Hotels near Leonard Field
445 Washington St, Winchester, MA 1890
Hotels near Leonard Field
Swipe to find hotels on the map.
- 1
Spark by Hilton Woburn Boston
- 2
Best Western Plus New Englander
- 3
Courtyard by Marriott Woburn / Boston North
- 4
Hilton Boston / Woburn
- 5
Homewood Suites by Hilton Boston Woburn
- 6
Hampton Inn Boston Woburn
- 7
Fairfield Inn by Marriott Boston Woburn-Burlington
- 8
Holiday Inn Express Boston North-Woburn by IHG
- 9
Crowne Plaza Boston - Woburn by IHG
- 10
Red Roof Inn PLUS+ Boston - Woburn / Burlington
- 11
Extended Stay America Suites Boston Woburn
- 12
Hyatt Place Boston / Medford
- 13
HYATT house Boston / Burlington
- 14
Boston Marriott Burlington
- 15
Residence Inn by Marriott Boston Woburn
Booking with a team?
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Which hotel fits best?
Best brands for youth sports tournaments and amenities that actually matter.
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Food, traffic, and game-day tips you won't find on other booking sites.
15 Hotels near Leonard Field
Multiple hotel sources, one search — rates you won't find on a single booking site.
Spark by Hilton Woburn Boston
Established standards upgraded specifically for athletes navigating compressed timelines and early starts.
- Fuel up at signature omelet stations with made-to-order breakfast creations
- Order snacks and drinks delivered directly to your poolside lounge area
- Keep dress footwear polished with available on-site shoeshine services
Best Western Plus New Englander
Known for delivering what youth sports families need most — dependable ease.
- Leverage same-day dry cleaning when available for special events
- Book connecting rooms to supervise players while maintaining privacy
- Unpack tournament gear in upgraded rooms with extra storage options
Courtyard by Marriott Woburn / Boston North
Polished service and predictable quality built for multi-room team bookings that matter.
- Grab localized breakfast favorites that feel like home away from home
- Ease muscle tension in the therapeutic whirlpool spa
- Prepare sharp looks using in-room iron and full ironing board
Hilton Boston / Woburn
The flagship that honors tradition while adapting to how families travel for competition.
- Secure adjoining rooms at booking for multi-family tournament travel convenience
- Gather your team in spacious separate living rooms
- Access multiple rental car companies at the convenient on-site desk
Homewood Suites by Hilton Boston Woburn
The brand that knows tired teams crave comfort and connection in equal measure.
- Sink into Serta Suite Dreams mattresses after every game day
- Fuel up with complimentary hot coffee available around the clock
- Fill plates with rotating eggs, meats, yogurt, and pastries
Hampton Inn Boston Woburn
Staff here treat rosters like family and fix problems before asked.
- Recharge on crisp white duvets designed for deep, restorative sleep
- Purchase cold beverages and snacks at twenty-four-hour Suite Shop
- Energize players with complimentary hot breakfast before every match
Booking 9+ rooms? Get group rates.
Fairfield Inn by Marriott Boston Woburn-Burlington
Globally trusted comfort designed for early alarms and quick turnarounds.
- Claim poolside lounge seating for team bonding time
- Tackle wrinkles fast using in-room iron and full-size ironing board
- Expand sleeping capacity with rollaway beds for bigger family groups
Holiday Inn Express Boston North-Woburn by IHG
This system prioritizes execution so teams can focus energy on performance only.
- Sleep through neighbors with acoustic headboard technology in every room
- Navigate easily through well-lit parking areas during early morning departures
- Select your ideal pillow firmness from the bedding collection options
Crowne Plaza Boston - Woburn by IHG
Targets travelers who want polished service and spaces that work for all ages.
- Ease muscle tension in the whirlpool between competition days
- Handle garment needs with professional on-site dry cleaning
- Experience improved room layout through thoughtful angled bed design
Red Roof Inn PLUS+ Boston - Woburn / Burlington
The brand that prioritizes sleep quality and quick turnarounds for traveling competitors.
- Request additional pillows for parents sharing rooms with athletes
- Grab energy snacks for players before competition or practice
- Warm up athletes with complimentary hot tea before cold morning games
Extended Stay America Suites Boston Woburn
Known for giving traveling families the space to spread out and recharge.
- Grab premium coffee and tea before early tournament starts
- Take advantage of pool facilities for post-competition cooldown
- Prepare polished looks with iron and ironing board in each suite
Hyatt Place Boston / Medford
Elevated midscale hospitality tailored to teams expecting more than basic lodging.
- Clean uniforms and warmups at accessible coin-operated laundry facility
- Settle into layouts that accommodate parents and players traveling together
- Relax on the signature sectional with plenty of seating space
HYATT house Boston / Burlington
Gives traveling teams the separation zones they need to truly decompress.
- Sleep better on pillow-top mattresses built for deep rest
- Power through tournaments with snacks available twenty-four seven at H Market
- Start game day with custom omelets built to order
Boston Marriott Burlington
Refined quality that respects tournament economics when booking rooms for the entire roster.
- Spread out in M Club rooms with upgraded square footage
- Charge electric cars conveniently while athletes rest and recover overnight
- Cleanse with This Works® products in spacious walk-in showers
Residence Inn by Marriott Boston Woburn
The brand that treats multi-day stays like home, not a hotel.
- Select ideal pillow firmness with down or down-alternative choices available
- Keep athletes energized with convenient grab-and-go snack options available always
- Fuel up with hot breakfast bowls customized for game day energy
Leonard Field Travel Guide
We built this guide so your team doesn't have to figure it all out from a Google search. Neighborhoods, restaurants, game day logistics, local tips — it's all here.
Welcome to Leonard Field in Winchester, Massachusetts, a vibrant hub for youth and amateur sports. This guide is designed for players, coaches, families, and visiting teams looking to make the most of their time at the field and in the surrounding community. We'll cover everything from arrival logistics and game day pacing to dining options and local attractions, ensuring a smooth and enjoyable experience for everyone involved in your team's visit.
Neighborhood Overview
Nestled in the charming town of Winchester, just northwest of Boston, Leonard Field benefits from a prime location that balances suburban tranquility with convenient access to metropolitan amenities. The field is situated off Washington Street, a main thoroughfare that connects you easily to Route 128/I-95, offering swift passage to and from the greater Boston area. For those arriving by air, Boston Logan International Airport (BOS) is approximately a 30-45 minute drive depending on traffic, and access via I-93 North is straightforward. Public transportation is also an option, with the MBTA Commuter Rail serving the Winchester Center station, located about a mile from the field. Parking is available on-site, but it can become congested during peak tournament times, so arriving early is highly recommended. Plan your travel to account for typical Boston-area rush hour traffic, especially if coming from or going to the city between 7-9 AM and 4-6 PM on weekdays. Utilizing GPS and checking real-time traffic apps is advised for the smoothest journey to the field.
Where to Stay
Leonard Field is surrounded by a residential neighborhood, with most lodging options found a short drive away in nearby towns like Woburn, Medford, or Burlington, or closer to Boston itself. While there are no hotels immediately adjacent to the field, Winchester Center offers a few local inns and bed & breakfasts, but larger hotel chains are concentrated along the Route 128 corridor. Many teams and families opt for hotels in Woburn or Burlington, which provide a good range of familiar accommodations and dining choices, all within a 10-15 minute drive of Leonard Field. Booking accommodations well in advance is crucial, particularly during spring and fall sports seasons when tournaments and league games are frequent. Utilizing map filters to search for hotels within a 5-10 mile radius and checking proximity to major highways like I-95 will help narrow down your best options. For groups seeking a more relaxed stay, consider areas with easy access to parks and local eateries for downtime between games.
Quick-Plan Overview
Getting There
Boston Logan International Airport (BOS) is about 30-45 minutes away by car, depending on traffic conditions.
Arrival & Parking
Arrive at least 30-45 minutes before game time to secure parking and find your team's area.
Food & Dining
Winchester Center offers charming cafes and small shops for a casual stroll or snack break.
Rainy Day Plan
The local library or nearby indoor sports facilities in Woburn can serve as a rainy-day alternative.
Food & Dining
Team meals or post-game gatherings can be found at family-friendly restaurants in Winchester or Woburn.
- Boston Logan International Airport (BOS) is about 30-45 minutes away by car, depending on traffic conditions.
- Arrive at least 30-45 minutes before game time to secure parking and find your team's area.
- Winchester Center offers charming cafes and small shops for a casual stroll or snack break.
- The local library or nearby indoor sports facilities in Woburn can serve as a rainy-day alternative.
- Team meals or post-game gatherings can be found at family-friendly restaurants in Winchester or Woburn.
Tournament Day Flow
Check-In & Warm-Up
Begin your arrival approximately 45 minutes before your scheduled game time. This buffer allows ample time for parking, especially during busy tournament days. Once parked, locate your designated field and begin setting up your team's base camp with chairs and shade structures. Coaches and players can utilize the open grassy areas around the fields for pre-game warm-ups and drills, ensuring everyone is ready to go when it's time for the official check-in with referees or tournament directors. Have all necessary player information and team rosters readily available.
Mid-Day Regroup
For teams with gaps between games or during longer tournament days, strategize your downtime. Utilize shaded areas near your field for players to rest, rehydrate, and have snacks from coolers. Families can explore the immediate vicinity for a brief walk or find a quiet spot to relax. This is also a good window to coordinate team meals or grab lunch from nearby food vendors or local eateries. Staying organized with hydration and nutrition is key to maintaining energy levels throughout the day and for subsequent games.
Wrap-Up & Departure
After your final game concludes, allow time for a proper cool-down and team debrief. Gather your equipment and personal belongings, ensuring no items are left behind. Take a moment for team photos or a quick post-game huddle. Factor in potential queues for parking lot exit during peak departure times. Consider a planned post-game gathering at a local restaurant or park to celebrate the team's effort before heading home, allowing ample time for travel back to your accommodations or onward destinations.
Check-In & Warm-Up
Begin your arrival approximately 45 minutes before your scheduled game time. This buffer allows ample time for parking, especially during busy tournament days. Once parked, locate your designated field and begin setting up your team's base camp with chairs and shade structures. Coaches and players can utilize the open grassy areas around the fields for pre-game warm-ups and drills, ensuring everyone is ready to go when it's time for the official check-in with referees or tournament directors. Have all necessary player information and team rosters readily available.
Mid-Day Regroup
For teams with gaps between games or during longer tournament days, strategize your downtime. Utilize shaded areas near your field for players to rest, rehydrate, and have snacks from coolers. Families can explore the immediate vicinity for a brief walk or find a quiet spot to relax. This is also a good window to coordinate team meals or grab lunch from nearby food vendors or local eateries. Staying organized with hydration and nutrition is key to maintaining energy levels throughout the day and for subsequent games.
Wrap-Up & Departure
After your final game concludes, allow time for a proper cool-down and team debrief. Gather your equipment and personal belongings, ensuring no items are left behind. Take a moment for team photos or a quick post-game huddle. Factor in potential queues for parking lot exit during peak departure times. Consider a planned post-game gathering at a local restaurant or park to celebrate the team's effort before heading home, allowing ample time for travel back to your accommodations or onward destinations.
Things to Do
Walkable
Winchester Town Center
1.1 miThe heart of Winchester offers a charming New England experience, perfect for a post-game stroll or a relaxed lunch break. Browse the local boutiques, grab a coffee at a cozy café, or simply enjoy the historic architecture and town green. It’s a pleasant area for families to stretch their legs and find some light refreshments, providing a nice contrast to the athletic fields. The town center is easily accessible by a short walk or a very quick drive from Leonard Field, making it a convenient option for downtime.
Abbot Downing Park
0.8 miLocated a short walk from Leonard Field, Abbot Downing Park provides a peaceful green space for relaxation and recreation. It features walking paths, picnic areas, and open fields suitable for casual play or simply unwinding between games. Families can enjoy the playground equipment, making it an ideal spot for younger siblings to burn off energy. The park offers a tranquil setting to escape the intensity of competition and enjoy some fresh air.
5–15 Minutes Away
The Fells Reservation
4.5 miJust a short drive from Leonard Field, The Fells is a sprawling reservation offering extensive hiking trails, scenic views of the lakes, and historic estate grounds. It's an excellent option for active families or groups looking to explore nature and enjoy some light physical activity away from the sports complex. The diverse terrain makes for enjoyable walks, and opportunities for birdwatching and enjoying the natural Massachusetts landscape are abundant. Pack some water and snacks for a longer exploration.
Middlesex Fells Reservoir
4.0 miThis vast reservoir and surrounding parkland offers a wealth of outdoor activities. Visitors can enjoy hiking and biking trails, fishing, and scenic drives around the water. The DCR administration building also has maps and information about the various access points and trails within the Fells. It’s a great spot for team outings or family relaxation, providing a beautiful natural escape within easy reach of Winchester. Many trails are well-maintained and offer varying degrees of difficulty.
Walkable
- Winchester Town Center — The heart of Winchester offers a charming New England experience, perfect for a post-game stroll or a relaxed lunch break. Browse the local boutiques, grab a coffee at a cozy café, or simply enjoy the historic architecture and town green. It’s a pleasant area for families to stretch their legs and find some light refreshments, providing a nice contrast to the athletic fields. The town center is easily accessible by a short walk or a very quick drive from Leonard Field, making it a convenient option for downtime. 1.1 mi
- Abbot Downing Park — Located a short walk from Leonard Field, Abbot Downing Park provides a peaceful green space for relaxation and recreation. It features walking paths, picnic areas, and open fields suitable for casual play or simply unwinding between games. Families can enjoy the playground equipment, making it an ideal spot for younger siblings to burn off energy. The park offers a tranquil setting to escape the intensity of competition and enjoy some fresh air. 0.8 mi
5–15 Minutes Away
- The Fells Reservation — Just a short drive from Leonard Field, The Fells is a sprawling reservation offering extensive hiking trails, scenic views of the lakes, and historic estate grounds. It's an excellent option for active families or groups looking to explore nature and enjoy some light physical activity away from the sports complex. The diverse terrain makes for enjoyable walks, and opportunities for birdwatching and enjoying the natural Massachusetts landscape are abundant. Pack some water and snacks for a longer exploration. 4.5 mi
- Middlesex Fells Reservoir — This vast reservoir and surrounding parkland offers a wealth of outdoor activities. Visitors can enjoy hiking and biking trails, fishing, and scenic drives around the water. The DCR administration building also has maps and information about the various access points and trails within the Fells. It’s a great spot for team outings or family relaxation, providing a beautiful natural escape within easy reach of Winchester. Many trails are well-maintained and offer varying degrees of difficulty. 4.0 mi
Food & Drink
Inside & Adjacent
Local Field Concessions
On siteWhen at Leonard Field, the on-site concessions are often the most convenient option for quick snacks and refreshments. They typically offer classic stadium fare like hot dogs, pretzels, drinks, and sometimes pizza or sandwiches, catering directly to players and spectators during games and tournaments. This is the go-to for grabbing something fast without leaving the venue, perfect for a quick bite between innings or during a brief break.
Tuscan Kitchen
3.2 miA short drive to Woburn brings you to Tuscan Kitchen, offering a high-quality Italian dining experience with an emphasis on fresh ingredients and authentic preparation. Known for its pasta, wood-fired pizzas, and impressive wine list, it's a sophisticated choice for a team dinner or a meal with visiting family. The atmosphere is lively yet refined, making it suitable for celebrating achievements or enjoying a well-deserved meal after a day of competition. Reservations are often recommended, especially for larger groups.
Nearby Gathering Spots
The Stand
0.4 miLocated conveniently on Washington Street near Leonard Field, The Stand is a popular spot offering a casual dining experience with a diverse menu. They serve up burgers, sandwiches, salads, and comfort food favorites, making it a family-friendly choice for grabbing a bite. It's a relaxed environment perfect for teams looking for a straightforward, satisfying meal close to the fields. Their outdoor seating can be a nice option during warmer months.
Biltmore Bar & Grille
1.2 miSituated in Winchester Center, the Biltmore Bar & Grille provides a lively atmosphere with a menu featuring American pub fare, seafood, and specialty cocktails. It’s a great place for teams or families to gather for a meal, offering a range of options to please different tastes. The pub-like setting makes it conducive to relaxed conversations and post-game analysis. They often have daily specials and a good selection of draft beers.
Local & Elevated Picks
Lucia Ristorante
1.3 miFor a more refined Italian dining experience, Lucia Ristorante in Winchester Center is an excellent choice. They focus on authentic regional Italian cuisine with a well-curated wine list, perfect for a special team occasion or a more intimate group dinner. The ambiance is warm and inviting, with attentive service that complements the quality of the food. It’s a place to savor a memorable meal and celebrate your team’s efforts.
Joe's American Bar & Grill
1.5 miJoe's American Bar & Grill offers a classic American dining experience with a broad menu that includes steaks, seafood, burgers, and salads. It’s a dependable option for groups seeking familiar favorites in a comfortable setting. The restaurant is known for its friendly service and consistent quality, making it a solid choice for a family-friendly meal after a day of sports. They can often accommodate larger groups with advance notice.
Inside & Adjacent
- Local Field Concessions — When at Leonard Field, the on-site concessions are often the most convenient option for quick snacks and refreshments. They typically offer classic stadium fare like hot dogs, pretzels, drinks, and sometimes pizza or sandwiches, catering directly to players and spectators during games and tournaments. This is the go-to for grabbing something fast without leaving the venue, perfect for a quick bite between innings or during a brief break. On site
- Tuscan Kitchen — A short drive to Woburn brings you to Tuscan Kitchen, offering a high-quality Italian dining experience with an emphasis on fresh ingredients and authentic preparation. Known for its pasta, wood-fired pizzas, and impressive wine list, it's a sophisticated choice for a team dinner or a meal with visiting family. The atmosphere is lively yet refined, making it suitable for celebrating achievements or enjoying a well-deserved meal after a day of competition. Reservations are often recommended, especially for larger groups. 3.2 mi
Nearby Gathering Spots
- The Stand — Located conveniently on Washington Street near Leonard Field, The Stand is a popular spot offering a casual dining experience with a diverse menu. They serve up burgers, sandwiches, salads, and comfort food favorites, making it a family-friendly choice for grabbing a bite. It's a relaxed environment perfect for teams looking for a straightforward, satisfying meal close to the fields. Their outdoor seating can be a nice option during warmer months. 0.4 mi
- Biltmore Bar & Grille — Situated in Winchester Center, the Biltmore Bar & Grille provides a lively atmosphere with a menu featuring American pub fare, seafood, and specialty cocktails. It’s a great place for teams or families to gather for a meal, offering a range of options to please different tastes. The pub-like setting makes it conducive to relaxed conversations and post-game analysis. They often have daily specials and a good selection of draft beers. 1.2 mi
Local & Elevated Picks
- Lucia Ristorante — For a more refined Italian dining experience, Lucia Ristorante in Winchester Center is an excellent choice. They focus on authentic regional Italian cuisine with a well-curated wine list, perfect for a special team occasion or a more intimate group dinner. The ambiance is warm and inviting, with attentive service that complements the quality of the food. It’s a place to savor a memorable meal and celebrate your team’s efforts. 1.3 mi
- Joe's American Bar & Grill — Joe's American Bar & Grill offers a classic American dining experience with a broad menu that includes steaks, seafood, burgers, and salads. It’s a dependable option for groups seeking familiar favorites in a comfortable setting. The restaurant is known for its friendly service and consistent quality, making it a solid choice for a family-friendly meal after a day of sports. They can often accommodate larger groups with advance notice. 1.5 mi
Local Tips
Traffic on Washington Street can be heavy during school drop-off/pickup and typical commuter hours: plan accordingly.
Weekend tournament days often see Leonard Field parking fill up quickly: arriving extra early is crucial.
Winchester Center is best explored on foot: parking can be limited during peak times like Saturdays.
Public parks are plentiful for downtime: , but check local regulations on team gatherings or food service at parks.
Seasonal note: The seasons paint a distinct picture around Leonard Field. Spring and early summer are vibrant with team sports, the fields bustling with activity under mild to warm weather, requiring light athletic gear and sun protection. Mid-summer can bring heat and humidity, making hydration and seeking shade paramount for players and spectators alike; outdoor dining on patios becomes popular. Fall offers crisp air and beautiful foliage, ideal for comfortable game days, though evenings can turn cool, necessitating layers. Winter sees the fields dormant, with sports shifting indoors, and the town takes on a quieter, cozy atmosphere, though holiday decorations add cheer. Rain can occur year-round, sometimes leading to cancellations or schedule adjustments, so always check official notices.
- Traffic on Washington Street can be heavy during school drop-off/pickup and typical commuter hours plan accordingly.
- Weekend tournament days often see Leonard Field parking fill up quickly arriving extra early is crucial.
- Winchester Center is best explored on foot parking can be limited during peak times like Saturdays.
- Local pharmacies and grocery stores are concentrated around Winchester Center and nearby commercial areas in Woburn.
- Public parks are plentiful for downtime , but check local regulations on team gatherings or food service at parks.
- Seasonal note: The seasons paint a distinct picture around Leonard Field. Spring and early summer are vibrant with team sports, the fields bustling with activity under mild to warm weather, requiring light athletic gear and sun protection. Mid-summer can bring heat and humidity, making hydration and seeking shade paramount for players and spectators alike; outdoor dining on patios becomes popular. Fall offers crisp air and beautiful foliage, ideal for comfortable game days, though evenings can turn cool, necessitating layers. Winter sees the fields dormant, with sports shifting indoors, and the town takes on a quieter, cozy atmosphere, though holiday decorations add cheer. Rain can occur year-round, sometimes leading to cancellations or schedule adjustments, so always check official notices.
Weather & Seasons
Winter
Winchester winters are cold with average temperatures often below freezing, bringing snow and ice. Visitors should pack heavy coats, hats, gloves, and waterproof boots. Games are rare on outdoor fields; check for indoor alternatives. Travel can be impacted by snowstorms, so monitor weather forecasts closely for any travel advisories or venue changes.
Spring & early summer
Spring and early summer offer mild to warm conditions, ideal for outdoor sports. Daytime temperatures are pleasant, but evenings can still be cool, so packing layers is advisable. Sunscreen, hats, and sunglasses are essential as the sun becomes stronger. Occasional spring showers can occur, so bring a light rain jacket or umbrella.
Mid-summer
Mid-summer in Winchester is typically warm to hot, with high humidity common, especially in July and August. Temperatures can reach the 80s and 90s Fahrenheit. Lightweight, breathable clothing is recommended, along with ample hydration. Sun protection is critical, and seeking shade during breaks is crucial. Be prepared for potential afternoon thunderstorms.
Fall season
Fall brings cooler, crisp air, making it a perfect time for outdoor activities. Daytime temperatures are often in the 50s and 60s Fahrenheit, but evenings can drop significantly. Layers are essential, including sweaters or light jackets. The foliage is beautiful, but outdoor events should still account for shorter daylight hours and potential wind or rain.
Rain & snow
Rain can occur in any season, sometimes leading to game delays or cancellations; always check the official schedule or venue updates. Snowfall is common in winter, potentially making roads hazardous and fields unplayable. Be prepared for wet conditions by packing rain gear and waterproof footwear, and for winter travel, ensure your vehicle is equipped for snow and ice conditions.
Winter
Winchester winters are cold with average temperatures often below freezing, bringing snow and ice. Visitors should pack heavy coats, hats, gloves, and waterproof boots. Games are rare on outdoor fields; check for indoor alternatives. Travel can be impacted by snowstorms, so monitor weather forecasts closely for any travel advisories or venue changes.
Spring & early summer
Spring and early summer offer mild to warm conditions, ideal for outdoor sports. Daytime temperatures are pleasant, but evenings can still be cool, so packing layers is advisable. Sunscreen, hats, and sunglasses are essential as the sun becomes stronger. Occasional spring showers can occur, so bring a light rain jacket or umbrella.
Mid-summer
Mid-summer in Winchester is typically warm to hot, with high humidity common, especially in July and August. Temperatures can reach the 80s and 90s Fahrenheit. Lightweight, breathable clothing is recommended, along with ample hydration. Sun protection is critical, and seeking shade during breaks is crucial. Be prepared for potential afternoon thunderstorms.
Fall season
Fall brings cooler, crisp air, making it a perfect time for outdoor activities. Daytime temperatures are often in the 50s and 60s Fahrenheit, but evenings can drop significantly. Layers are essential, including sweaters or light jackets. The foliage is beautiful, but outdoor events should still account for shorter daylight hours and potential wind or rain.
Rain & snow
Rain can occur in any season, sometimes leading to game delays or cancellations; always check the official schedule or venue updates. Snowfall is common in winter, potentially making roads hazardous and fields unplayable. Be prepared for wet conditions by packing rain gear and waterproof footwear, and for winter travel, ensure your vehicle is equipped for snow and ice conditions.
Venue Facts
Primary team
Youth and amateur sports leagues
Neighborhood
West side of Winchester, near residential areas
Nearest airport
Boston Logan International (BOS)
Parking
On-site lot, can fill quickly
Walkable district
Winchester Center (1.1 miles)
Groceries & supplies
Winchester Center or nearby Woburn commercial areas
Pharmacy
CVS or Walgreens in Winchester Center
Urgent care
Immediate Care Center in Woburn or Winchester Hospital Urgent Care
Downtime
Abbot Downing Park, Winchester Center, or The Fells Reservation
Pro tip
Arrive early on tournament days to secure preferred parking and team setup spots.
| Primary team | Youth and amateur sports leagues |
| Neighborhood | West side of Winchester, near residential areas |
| Nearest airport | Boston Logan International (BOS) |
| Parking | On-site lot, can fill quickly |
| Walkable district | Winchester Center (1.1 miles) |
| Groceries & supplies | Winchester Center or nearby Woburn commercial areas |
| Pharmacy | CVS or Walgreens in Winchester Center |
| Urgent care | Immediate Care Center in Woburn or Winchester Hospital Urgent Care |
| Downtime | Abbot Downing Park, Winchester Center, or The Fells Reservation |
| Pro tip | Arrive early on tournament days to secure preferred parking and team setup spots. |
Frequently Asked Questions
Real questions travelers ask before booking near Leonard Field — answered with the specifics you actually need.
Questions Travelers Ask What people want to know before booking near Leonard Field
What are the closest hotels to Leonard Field?
The closest hotel to Leonard Field is Spark by Hilton Woburn Boston (1.93 mi, from $157/night) — a 4-minute drive. Other nearby options include Best Western Plus New Englander (2 mi, from $132/night) and Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night). Spark by Hilton Woburn Boston offers free breakfast, a pool, and a fitness center. Best Western Plus New Englander offers free breakfast, a pool, and a fitness center. Courtyard by Marriott Woburn / Boston North offers free breakfast, a pool, and a fitness center.
Which hotels near Leonard Field are good for families?
Several hotels near Leonard Field are well-suited for families. Spark by Hilton Woburn Boston (1.93 mi, from $157/night), Best Western Plus New Englander (2 mi, from $132/night), and Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night) all offer suites, connecting rooms, a pool, complimentary breakfast, and on-site laundry.
Which hotels near Leonard Field are good for team or group travel?
Several hotels near Leonard Field accommodate team and group travel. Crowne Plaza Boston - Woburn by IHG (4.54 mi, from $154/night), Spark by Hilton Woburn Boston (1.93 mi, from $157/night), and Best Western Plus New Englander (2 mi, from $132/night) all offer meeting space, complimentary breakfast, and on-site laundry. Crowne Plaza Boston - Woburn by IHG also has bus or oversized vehicle parking.
Are there extended-stay hotels near Leonard Field?
Yes — Homewood Suites by Hilton Boston Woburn (4.01 mi, from $286/night), Extended Stay America Suites Boston Woburn (5.1 mi, from $134/night), and HYATT house Boston / Burlington (6.04 mi, from $199/night) are all extended-stay properties near Leonard Field, with full kitchens and on-site laundry.
Are there upscale or luxury hotels near Leonard Field?
Several upscale hotels are available near Leonard Field. Spark by Hilton Woburn Boston (1.93 mi, from $157/night), Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night), and Hilton Boston / Woburn (3.62 mi, from $148/night) all offer on-site dining, room service, and a pool.
Hotel Amenities & Features Pools, breakfast, pet policies, and more
Which hotels near Leonard Field offer free breakfast?
Best Western Plus New Englander (2 mi, from $132/night), Homewood Suites by Hilton Boston Woburn (4.01 mi, from $286/night), and Hampton Inn Boston Woburn (4.05 mi, from $305/night) include complimentary breakfast.
Can I get early check-in at hotels near Leonard Field?
Spark by Hilton Woburn Boston (1.93 mi, from $157/night), Best Western Plus New Englander (2 mi, from $132/night), and Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night) may offer early check-in upon request, subject to availability. Call ahead to confirm — especially helpful for morning games or early events.
Which hotels near Leonard Field have laundry facilities?
Spark by Hilton Woburn Boston (1.93 mi, from $157/night), Best Western Plus New Englander (2 mi, from $132/night), and Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night) have guest laundry facilities on-site.
Which hotels near Leonard Field have suites or extra space?
Spark by Hilton Woburn Boston (1.93 mi, from $157/night), Best Western Plus New Englander (2 mi, from $132/night), and Courtyard by Marriott Woburn / Boston North (2.86 mi, from $214/night) offer suite-style rooms with extra living space.
Which hotels near Leonard Field have a full in-room kitchen?
Homewood Suites by Hilton Boston Woburn (4.01 mi, from $286/night), Extended Stay America Suites Boston Woburn (5.1 mi, from $134/night), and HYATT house Boston / Burlington (6.04 mi, from $199/night) offer rooms with a full kitchen — stove, full-size fridge, and dishwasher.
Other sports fields nearby
Also planning a multi-venue trip? Check these within 50 miles.
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