The best deals on hotels near The Winchendon School in Winchendon, MA.
Access unmatched hotel rates and frequent flash deals on rooms.
Save up to 70% when booking as a group. Select 9+ rooms to get started.
Top 24 Hotels Near The Winchendon School
172 Ash St Winchendon, MA 1475
Gardner Inn
For a trip to the area, Gardner Inn's role as a practical base is a foundational part of its convenience.
Arrivals at Gardner Inn may present a simple reception, self-serve coffee, and accessible parking configured for routine travel. Standard guest rooms may include hardwood floors, modest seating, and in-room coffee stations that add to the balance of each stay. Shared spaces may feature vending machines, breakfast counters, and modest lobbies that reinforce straightforward travel convenience daily.
Guests may enjoy Wi-Fi, laundry facilities, vending access, and breakfast counters, reinforcing reliable support during travel stays.
The Colonial Hotel
The hotel's regional location is a strategic choice, serving as a practical base with The Winchendon School within driving reach.
At The Colonial Hotel, guests are often greeted with boutique interiors, artisanal coffee, and staff focused on creating a personal welcome. Rooms typically offer curated décor, plush bedding, and artisanal details for a boutique-forward and polished guest experience. Shared spaces may include small libraries, stylish cocktail bars, and curated lounges designed to reflect boutique hospitality.
Guests may enjoy artisanal breakfast, self-serve markets, Wi-Fi, and laundry facilities, ensuring flexibility for longer boutique visits.
The Birchwood Inn
From the lobby of The Birchwood Inn, The Winchendon School is a simple commute with no stress, simplifying your visit.
Guests at The Birchwood Inn may encounter cozy lobby areas, curated design, and warm boutique-style reception from attentive staff. Guest rooms may feature premium bedding, unique interiors, and curated minibars that contribute to a stylish boutique stay. Facilities often highlight cozy lounges, locally inspired dining, and art-focused interiors that create a boutique guest experience.
A stay may present complimentary Wi-Fi, bike storage, laundry service, and family-friendly dining, reinforcing ease across guest stays.
Riverhouse by Weekender (Formerly Jack Daniels Inn)
The benefit of using Riverhouse by Weekender (Formerly Jack Daniels Inn) as a practical base renders it into a great anchor point before the main experience.
Riverhouse by Weekender (Formerly Jack Daniels Inn) often provides an uncomplicated desk experience, on-site parking, and a compact lobby aimed at keeping wait times low. Accommodations often highlight comfortable bedding, Wi-Fi, and compact work surfaces, providing guests with simple and functional routines. Facilities often include guest laundries, vending corners, and compact business areas that create balance for both rest and productivity.
A stay often highlights Wi-Fi, vending areas, modest breakfast, and guest laundries, helping sustain clear routines for daily visitors.
Doubletree by Hilton Hotel Leominster
The Winchendon School is within driving reach from Doubletree by Hilton Hotel Leominster, a convenience that allows for easy travel to other local points.
The grab-and-go market at DoubleTree lets families reset with snacks on arrival, easing the transition before unpacking and planning. Guest rooms provide multiple USB and charging points, ensuring business and leisure travelers keep devices powered at all times. Pools provide heated water and sundecks with chairs, offering recharge opportunities and comfortable rest after long flights or events.
Complimentary Wi-Fi, breakfast stations, indoor pools, laundry service, and valet simplify routines, supporting clarity and reliability.
Comfort Inn & Suites Brattleboro I-91
In the Winchendon region, Comfort Inn & Suites Brattleboro I-91's role as a practical base lets guests commute easily to The Winchendon School before their stay.
Comfort Inn arrival spaces balance durable floor finishes and welcoming textiles to support high traffic while signaling care. Guest rooms supply USB ports and bedside charging as well as task lamps at desks, letting devices power up while you check messages quickly. Club lounges may serve evening appetizers or a light breakfast, turning the space into an easy default for quick, quiet meals.
From laundry, mini-fridges, free breakfast, meeting space, Wi-Fi, and on-site dining, extended stays keep routines intact and workdays productive.
Motel 6 Leominster MA
Guests at Motel 6 Leominster MA can appreciate it as a sensible base, with The Winchendon School an easy regional drive away.
Motel 6 integrates lobby lighting and acoustics for composure, setting a calm tone that softens the transition from transit to stay. All guest rooms supply simple work areas with tables and chairs, offering practical space for planning, reading, or laptop use daily. Lobby coffee stations carry lids and sleeves, so guests can take hot cups safely to rooms when mornings require quick, simple starts.
With free coffee in lobbies, vending areas, and Wi-Fi throughout, amenities keep mornings clear and daily routines uninterrupted.
Chocksett Inn and Restaurant
For a trip where a straightforward drive is essential, Chocksett Inn and Restaurant serves as a practical base for reaching The Winchendon School.
Chocksett Inn and Restaurant often greets arrivals with curated furnishings, locally inspired décor, and complimentary refreshments for guests. Accommodations often highlight artisanal décor, refined furnishings, and boutique bathrooms that create a personalized retreat. Amenities may present artisanal cafés, farm-to-table restaurants, and cocktail bars that reinforce boutique creativity and style.
Accommodations often feature Wi-Fi, yoga mats, breakfast options, and laundry service, creating consistency in boutique travel routines.
Best Western Plus Keene Hotel
For a trip to the area, Best Western Plus Keene Hotel's location as a practical base is an essential element of its practical charm.
Where shuttles operate, Best Western marks pickup points near the doors, converting transfers into simple, directed movement after check-in. Every guest room typically features a shower/tub combo, reliable water pressure, and refillable toiletries, making quick refreshes simple. Indoor pools at select hotels include loungers, towel stations, and nearby restrooms, creating low-effort recovery that fits busy schedules.
Between indoor pools where available, fitness access, breakfast service, and vending, guests weave wellness and fuel into busy days without friction.
Courtyard by Marriott Keene Downtown
For a trip to the area, Courtyard by Marriott Keene Downtown's location as a practical base is an essential component of the guest journey.
Lobby seating at Courtyard uses modular clusters and tables, creating natural hubs where families or teams can regroup comfortably. Every suite includes rainfall showers, marble vanities, and premium toiletries, refreshing guests with daily spa-quality rituals. The fitness studio with treadmills, bikes, and mats ensures wellness routines remain dependable during extended travel days.
Amenities include outdoor pools, pet-friendly policies, Wi-Fi, and meeting rooms, ensuring family routines and professional needs align.
Hampton Inn & Suites Keene
For travelers with a wide-ranging itinerary, Hampton Inn & Suites Keene is a practical base, keeping The Winchendon School an easy regional drive away.
Sofa groupings throughout Hampton Inn lobbies form intuitive pause points, creating comfort zones for families to rest together. Guest rooms feature televisions, sofa seating, and blackout drapes, combining relaxation with restful comfort for traveling families. Breakfast areas with cereal bars, hot buffets, and pastries create reliable structure, ensuring mornings begin smoothly every day.
On-site markets, complimentary internet, indoor pools, breakfast bags, and laundry services ensure ease that keeps daily travel smooth.
Fairfield Inn & Suites by Marriott Keene Downtown
Reaching The Winchendon School from Fairfield Inn & Suites by Marriott Keene Downtown is an easy regional drive, a trait that allows for a more flexible daily schedule.
Upon arrival, Fairfield Inn guides guests toward a compact lobby core—desk, market, and seating—so first choices remain clear and immediate. All guest rooms contain mini-fridges, microwaves, and coffee makers, letting families maintain routines with ease during extended hotel stays. Breakfast halls deliver hot options, fruit, and oatmeal, ensuring guests can establish consistent and healthy morning starts across stays.
Amenities such as 24/7 Market access, fitness equipment, complimentary Wi-Fi, and breakfast service provide clear routines that reduce daily stress.
HOLIDAY INN EXPRESS KEENE
For a trip to the area, HOLIDAY INN EXPRESS KEENE's role as a sensible base is a fundamental part of its convenience.
Holiday Inn Express lobbies blend lounge seating and communal work tables, supporting productivity alongside relaxed conversation. Each guest room provides ergonomic chairs, spacious desks, and Wi-Fi, giving business travelers a reliable work-ready environment. Breakfast dining areas filled with cereals, fruit, and hot dishes keep morning routines stress-free and clear for all types of travelers.
Free breakfast, self-parking, and Wi-Fi combine with business spaces and fitness centers, delivering consistency across properties.
Keene Elm City Hotel an Ascend Collection Hotel
From Keene Elm City Hotel an Ascend Collection Hotel, The Winchendon School is an easy regional drive, a detail that enhances the feeling of being well-situated.
At Keene Elm City Hotel an Ascend Collection Hotel, arrivals may feature efficient reception, vending options, and close parking that favor practical guest routines. Rooms may include premium linens, rainfall showers, and hardwood floors that contribute to a practical yet stylish environment for rest. Public areas may highlight breakfast rooms, vending stations, and modest seating that emphasize a simple and consistent guest routine.
Accommodations may present Wi-Fi, vending machines, breakfast service, and laundry rooms, maintaining practical balance in budget hotels.
Days Inn by Wyndham Keene NH
As a sensible base, Days Inn by Wyndham Keene NH is a key aspect that enhances the freedom of the guest.
From entrance to desk, Days Inn maintains open sightlines so new arrivals identify staff and next steps quickly day or night for clarity. Every guest room clusters microwave, refrigerator, and coffee supplies together, turning short windows into simple, no-drive meals. Fitness rooms line treadmills, bikes, and free weights beside towel bins and water, maintaining familiar routines without leaving property.
For families, breakfast seating, Wi-Fi, and a fitness room connect with a pool where available and towels, keeping routines balanced.
SpringHill Suites by Marriott Boston Devens Common Center
In Winchendon, SpringHill Suites by Marriott Boston Devens Common Center is situated as a practical base, which creates a sense of calm.
Guests find bright reception zones and clear layouts at SpringHill Suites, providing intuitive navigation that reduces stress and confusion. Suites are designed with west elm furnishings, lounge seating, and modern décor, creating stylish retreats that feel both comfortable and functional. The breakfast space provides eggs, fruit, and baked goods with hot coffee, helping travelers establish consistent routines every morning.
Amenities include indoor pools, breakfast with quality coffee, 24/7 Market access, and self-parking, ensuring stays remain convenient and clear.
Hilton Garden Inn Devens Common
In the Winchendon area, Hilton Garden Inn Devens Common has a accessible location, serving as a convenient base for visiting The Winchendon School.
Statement lighting and regional décor in Hilton Garden Inn receptions reinforce polished design, offering guests welcoming first impressions. Suites offer sofa beds, televisions, and lounge seating, creating versatile living areas that balance relaxation with shared family use. Pavilion Pantry markets with packaged meals, bottled drinks, and frozen items deliver immediate convenience that reduces travel stress.
Complimentary breakfast, valet parking, indoor pools, business lounges, and Wi-Fi deliver ease and efficiency across extended stays.
Nashoba Valley Inn & Suites
This useful role as a base is a defining feature of Nashoba Valley Inn & Suites, since it frames a stay built around easy travel.
Guests at Nashoba Valley Inn & Suites may encounter a no-nonsense front desk, modest lobby chairs, and parking access for stress-reduced arrivals. Each guest room typically provides climate control, compact seating, and in-room coffee, reinforcing comfort and daily travel routines. Shared spaces typically provide vending access, guest laundries, and compact lobbies that reflect the functional focus of budget hotels.
A visit may offer Wi-Fi, guest laundry, vending corners, and compact breakfast areas, sustaining clarity for everyday guest routines.
The Inn at Crumpin Fox
Serving as a sensible base, The Inn at Crumpin Fox keeps The Winchendon School an easy regional drive away.
The Inn at Crumpin Fox typically offers quick desk service, self-serve beverages, and on-site parking so guests can settle in with minimal delay. Guest rooms may feature hardwood floors, tasteful décor, and blackout curtains that help ensure rest and privacy during overnight stays. Facilities may showcase modest breakfast spaces, vending corners, and coin-operated laundry that sustain clarity and convenience daily.
Guests may encounter Wi-Fi, modest breakfast, vending access, and parking, reflecting straightforward support across budget properties.
Blue Bear Inn
In the Winchendon region, Blue Bear Inn boasts a strategic location, serving as a practical base for visiting The Winchendon School.
Arrivals at Blue Bear Inn may include an elegant lobby, attentive concierge presence, and complimentary coffee or tea during check-in. Accommodations may include upscale décor, plush bedding, and spa-style bathrooms that highlight a polished and comfortable retreat. Amenities typically include elegant lounges, stylish cocktail bars, and spa-style spaces that highlight a polished guest impression.
Guests may enjoy elegant dining, wellness areas, valet support, and Wi-Fi, aligning indulgent experiences with dependable convenience.
Hampton Inn Nashua
Within the region, Hampton Inn Nashua serves as a practical base, keeping The Winchendon School within driving reach.
Community tables in Hampton Inn receptions foster relaxed connection, giving colleagues or friends functional spaces to plan ahead. Each suite offers vanities with bright lighting, rainfall showers, and premium bath amenities, supporting morning and evening refresh routines. Fitness centers with rowing machines, treadmills, and free weights allow wellness continuity, letting guests recharge through exercise.
Complimentary breakfast, pet services, outdoor pools, business centers, and Wi-Fi connectivity give guests balance across leisure and work.
The Boxboro Regency
The benefit of using The Boxboro Regency as a convenient base turns it into a great starting point before the main experience.
At The Boxboro Regency, arrivals may highlight cozy seating, boutique details, and staff offering tailored service for each guest. Rooms may showcase eclectic design, curated minibars, and plush bedding that reflect boutique hospitality and comfort. Shared spaces often provide intimate bars, eclectic lounges, and co-working corners that emphasize boutique orientation and comfort.
A visit may highlight complimentary Wi-Fi, bike rentals, EV charging, and laundry support, offering boutique practicality and balance.
Motel 6 Nashua NH - North
Reaching The Winchendon School from Motel 6 Nashua NH - North is an easy regional drive, a trait that weaves convenience into the start of any day.
Motel 6 underscores first impressions with free morning coffee, signaling basic care while keeping the check-in lane efficient and clear. Guest rooms combine climate control, Wi-Fi, and entertainment, creating a consistent foundation that keeps stays predictable and comfortable. Self-service laundry rooms provide change or card options and folding space, allowing travelers to keep wardrobes organized across weeks.
Between pools, guest laundry, and vending plus Wi-Fi, properties balance relaxation, upkeep, and connectivity in one predictable mix.
Econo Lodge Brattleboro
As a convenient base, Econo Lodge Brattleboro is a central element that connects the hotel to the area's highlights.
At check-in, Econo staff commonly offer luggage storage and local directions so guests can explore before rooms are ready without burden. Each guest room balances premium bedding, a dedicated desk, a coffee maker and free Wi-Fi so sleep and short remote work remain feasible. Conference suites contain HDMI inputs, whiteboards and modular chairs that let organizers pivot quickly from presentation to workshop modes.
With free Wi-Fi, a hot buffet or grab-and-go, meeting rooms, a fitness corner, laundry and EV charging at select sites, travel runs smoother.
Book as a group & pay separately.
Lowest Group Rate Guaranteed.
The Winchendon School Local Area Guide
Event & Visitor Overview – The Winchendon School
The Winchendon School is a prep boarding school that hosts a mix of high-school-level athletics, weekend tournament play, school performances, admissions events, and occasional regional youth competitions. Typical visitors include students and boarding families, visiting student-athletes, parents and youth coaches, admissions guests, and alumni who return for seasonal matches or special ceremonies. Athletic use centers on school teams and interscholastic competition at the high school level, while weekday visitor traffic often comes from prospective families and academic or arts events. Trips tend to be organized around game schedules, tournament brackets, and key calendar moments such as season openers, homecoming-style weekends, and staged performances that draw repeat visitors from the New England prep community.
Day-of flowGame & Event Day Rhythm
Event days commonly follow a full-day rhythm with early warm-ups, mid-day competition windows, and evening finales for marquee matches or performances. For multi-team tournaments, fields or courts see continuous rotation throughout the day with scheduled downtime between games for warm-ups, team meetings, and field turnover; parents often arrive well before the first match and space out their visits across the day. Weekday contests are usually compact affairs that wrap up in the evening, while weekend tournaments can fill the venue from morning through late afternoon with bracket play and short breaks between sessions. Performance evenings follow a different cadence, with rehearsals earlier in the day and audience arrival concentrated 30–60 minutes before curtain. Post-event dispersal is staggered, with many families leaving soon after final scores or bows, and a smaller group lingering for debriefs or social time.
Getting thereTravel & Arrival Patterns
Most attendees travel by car from the surrounding New England region, making day trips common for families and local teams; some visitors plan overnight stays when schedules include multiple games or when coming from farther afield. Admissions visitors and alumni sometimes arrive the night before for early-morning activities or full-day events, while tournament teams often schedule staggered arrivals to accommodate warm-up windows. Expect clear surges in traffic just before high-profile starts and a concentrated departure period immediately after final matches or performances. Staying somewhere nearby simplifies timing on busy event days, and many groups coordinate arrival times with team coaches or event organizers to avoid congestion.
Weather checkWeather & Seasonal Considerations
New England seasonality shapes comfort and gear choices: late fall through early spring often brings cold, wind, and occasional snow that affect outdoor sports and spectator comfort, while spring can be wet and variable, producing muddy fields and rain delays. Summers deliver warmer, sometimes humid conditions that make shade, sun protection, and hydration important for daylong tournaments. Layering is practical for shifting daytime warmth and cooler evenings; waterproof outerwear and covered seating help during spring showers, and breathable clothing plus sun protection improve comfort for extended outdoor activity in summer months. Plan for earlier start times in colder months and for potential short-notice schedule changes when precipitation is likely.

