The best deals on hotels near Chester River Yacht & Country Club in Chestertown, MD.
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 Chester River Yacht & Country Club
7738 Quaker Neck Rd Chestertown, MD 21620
Red Roof Inn & Suites Chestertown
From Red Roof Inn & Suites Chestertown, the uncomplicated run to Chester River Yacht & Country Club avoids complex roads for a clear journey, making travel easy.
The lobby at a Red Roof Inn is a hub of practicality, offering vending machines and local information to help guests get their bearings. The durable, hard-surface flooring in NextGen guest rooms is a practical feature that enhances the overall cleanliness of the space. On-site laundry facilities are a budget-friendly feature, allowing guests to avoid higher costs associated with outside cleaning services.
For a truly budget-conscious trip, the hotel combines a pets-stay-free rule with free Wi-Fi, free coffee, and free premium television.
Comfort Inn & Suites Chestertown
The journey from Comfort Inn & Suites Chestertown to Chester River Yacht & Country Club is a simple drive, a benefit that contributes to a hassle-free visit.
Comfort Inn reception desks are sized to allow personal engagement while keeping check-in lines moving during peak arrival windows. Every guest room supplies a safe and discreet storage nook that secures valuables while the room stays tidy and work-ready. Breakfast counters often place coffee taps beside grab-and-go shelves so early departures fuel up and keep tight itineraries on track.
From business centers and meeting rooms to reliable Wi-Fi and event parking, companies run briefings without leaving the property.
Baltimore Marriott Inner Harbor at Camden Yards
In the Chestertown area, Baltimore Marriott Inner Harbor at Camden Yards has a accessible location, acting as a practical base for visiting Chester River Yacht & Country Club.
Lobby seating with charging hubs allows Marriott guests to reset devices and regroup while waiting on companions to complete check-in. Each guest room includes blackout curtains, plush bedding, and digital climate systems, designed to deliver deep, restorative sleep. The pool deck includes seating, towel service, and family-friendly access, offering both relaxation and recreation during leisure hours.
Breakfast buffets, EV charging, and on-site dining pair with meeting spaces and business centers, making travel efficient and balanced.
BWI Suites
When staying in the Chestertown area, the uncomplicated drive from BWI Suites to Chester River Yacht & Country Club is a low-stress start to the day.
Guests at BWI Suites may encounter basic reception service, vending machines, and convenient parking options for daily guest use. Each guest room often includes ergonomic seating, compact work surfaces, and Wi-Fi, helping maintain productivity while away from home. Facilities may include coin-operated laundries, vending areas, and compact business corners that allow for simple guest productivity.
A stay often highlights Wi-Fi, vending access, modest breakfast, and guest laundries, reinforcing practical balance during daily travel.
Holiday Inn Express Annapolis East-Kent Island by IHG
When travel in the Chestertown area is a factor, Holiday Inn Express Annapolis East-Kent Island by IHG's position as a sensible base is a major benefit.
Reception staff at Holiday Inn Express remain visible and attentive, creating reliable first impressions and dependable orientation. All guest rooms provide flat-screen TVs, plush beds, and blackout curtains, making restful sleep and easy relaxation predictable. Fitness facilities stocked with ellipticals, treadmills, and weights enable travelers to keep wellness routines intact during trips.
Meeting rooms, breakfast buffets, and Wi-Fi pair with fitness centers and parking, covering the essentials for balanced travel.
Quality Inn Grasonville near Kent Island
Within the region, Quality Inn Grasonville near Kent Island acts as a sensible base, a fact that lets the hotel to feel both convenient and calm.
With canopy access and direct curb pulls Quality Inn eases vehicle handoffs so guests step inside without long walks to the desk. Every suite pairs multiple lighting zones with task surfaces, improving screen visibility for work while preserving a relaxed evening ambience. Fitness centers combine treadmills, ellipticals, and free weights with towel service and water stations so brief workouts fit naturally between plans.
Fitness centers and pool access provide easy on-property spots to recharge so guests maintain wellness between flights or sessions.
Best Western Kent Narrows Inn
Because Best Western Kent Narrows Inn is a sensible base, guests can plan on a simple commute to Chester River Yacht & Country Club.
With covered entries and automatic doors, Best Western smooths the handoff from curb to lobby, preserving calm when weather or luggage complicate timing. Each suite supports fast Wi-Fi, HDMI-friendly TVs, and plentiful outlets, so presentations or media sharing stay smooth without setup delays. The café seating zone keeps outlets within reach, letting travelers sync devices while reviewing routes before heading back out.
With parking, EV stations where available, Wi-Fi, and breakfast, mobility and morning clarity connect smoothly across changing plans.
Hyatt Place Kent Narrows & Marina
This convenient base helps Hyatt Place Kent Narrows & Marina guests get like they are part of the local Chestertown scene without a major commute.
Communal seating and long tables in Hyatt Place lobbies provide flexible spaces for families or teams to regroup comfortably on arrival. Guest rooms provide branded bath products, walk-in showers, and soft lighting, refreshing daily routines with comfort and consistency. Meeting rooms with flexible layouts, AV equipment, and breakout tables support professional groups with seamless collaboration.
Pet-friendly policies, hot breakfast, and free Wi-Fi join with fitness centers and parking, creating dependable travel convenience.
Hilton Garden Inn Kent Island Marina
In the Chestertown region, Hilton Garden Inn Kent Island Marina's role as a sensible base lets guests travel easily to Chester River Yacht & Country Club before their stay.
Statement lighting and regional décor in Hilton Garden Inn receptions reinforce polished design, offering guests welcoming first impressions. All guest rooms provide ergonomic workstations, strong Wi-Fi, and multiple outlets, ensuring reliable productivity during every stay. Breakfast areas with pastries, coffee stations, and hot buffets create reliable clarity that helps mornings begin smoothly every day.
Complimentary internet, on-site dining, hot breakfast, business centers, and fitness rooms create balanced support for guest routines.
SpringHill Suites Baltimore White Marsh / Middle River
From the moment you leave SpringHill Suites Baltimore White Marsh / Middle River, Chester River Yacht & Country Club is within driving reach to get there easily, simplifying your plans.
SpringHill Suites emphasizes the little extras—infused water, grab-and-go snacks, bright seating—that make arrivals feel cared for and refreshed. Guest rooms include plush bedding, blackout shades, and adjustable thermostats, creating personalized conditions that promote restorative sleep. The market pantry offers drinks, light snacks, and late-night options, giving travelers dependable access to convenience around the clock.
Free Wi-Fi, hot breakfast variety, on-site parking, and indoor pool access together ensure essential comforts remain accessible during any stay.
Delta Hotels by Marriott Baltimore North
Guests at Delta Hotels by Marriott Baltimore North can appreciate it as a sensible base for visiting Chester River Yacht & Country Club and the wider region.
With bottled water, coffee service, and infused water, Delta Hotels provides small rituals that balance consistency and convenience. Guest rooms highlight blackout curtains, premium bedding, and coffee makers, supporting restful sleep and energized mornings daily. Guests enjoying the market encounter grab-and-go snacks, bottled drinks, and frozen items, dependable options that simplify routines.
With self-parking, hot breakfast buffets, meeting facilities, and fitness centers, travelers benefit from convenience and consistency.
The Inn at Chesapeake Bay Beach Club
Guests at The Inn at Chesapeake Bay Beach Club can depend on it as a sensible base to set a relaxed and convenient tone for their stay.
Arrivals at The Inn at Chesapeake Bay Beach Club may include an elegant lobby, attentive concierge presence, and complimentary coffee or tea during check-in. Rooms typically include upscale interiors, plush linens, and spa-style bathrooms designed to reflect an elegant and luxury-forward stay. Property amenities often showcase refined lounges, cocktail bars, and upscale restaurants that create a sophisticated guest impression.
Guests may enjoy wellness centers, cocktail bars, Wi-Fi, and valet parking, offering refined consistency across diverse travel routines.
Kent Island Resort
For guests in the Chestertown region, Kent Island Resort is a convenient base, a spot that makes for an unhurried start to the day.
Kent Island Resort often greets arrivals with curated interiors, boutique reception, and complimentary coffee or tea for a warm first impression. Accommodations often provide eclectic décor, curated minibars, and unique design details that emphasize boutique hospitality. Facilities often present farm-to-table dining, eclectic lounges, and art-focused interiors for a polished boutique guest experience.
A visit may present Wi-Fi, artisanal breakfast, laundry support, and bike rentals, sustaining boutique practicality during travel.
Motel Edgewood
From Motel Edgewood, Chester River Yacht & Country Club is within driving reach, a perk that makes the hotel a strategic choice.
Guests at Motel Edgewood may encounter compact lobbies, vending access, and exterior room entries that emphasize no-frills practicality. Rooms may provide climate control, modest desks, and Wi-Fi, reinforcing practical comfort throughout overnight stays. Facilities may highlight vending access, modest lobbies, and laundry rooms that reflect the functional focus of budget accommodations.
A stay may feature Wi-Fi, ice machines, vending access, and exterior parking, helping maintain straightforward guest routines each day.
Super 8 by Wyndham Baltimore / Essex Area
The journey from Super 8 by Wyndham Baltimore / Essex Area to Chester River Yacht & Country Club is an easy regional drive, a benefit that contributes to a cohesive and convenient visit.
Reception areas at Super 8 are brightly lit and staffed 24/7, supporting dependable service and orientation clarity for all guests. Suites add sofa seating, larger layouts, and additional televisions, ensuring families have flexible spaces for work and play. Business corners offering computers, Wi-Fi, and printing access support professionals with reliable setups for work efficiency.
Business corners, Wi-Fi, and complimentary breakfast connect with laundry and parking, creating reliable support for business travel.
Element Arundel Mills BWI Airport
Because Element Arundel Mills BWI Airport is a sensible base, guests can opt to get to Chester River Yacht & Country Club refreshed after an easy drive.
Element emphasizes orientation clarity through open lobby layouts, ensuring first-time guests navigate arrivals with ease and confidence. Suites include ergonomic desks, comfortable chairs, and complimentary Wi-Fi, helping travelers balance work tasks smoothly during long stays. Indoor pools include clean towels, safe depth markers, and natural décor, giving families reliable leisure areas to relax after daily activities.
Amenities like outdoor patios with BBQ grills, complimentary Wi-Fi, self-parking, and pet-friendly policies ensure flexibility during each stay.
Americas Best Value Inn Edgewood
Within the region, Americas Best Value Inn Edgewood acts as a sensible base, a fact that lets the hotel to feel both convenient and calm.
Americas Best Value Inn arrival lighting balances task and ambient layers so guests see staff, signage, and points of interest comfortably. Guest rooms include bedside USB ports, task lamps, and reachable outlets so devices stay charged and routines remain uninterrupted overnight. Breakfast areas arrange hot items, pastries, and coffee taps with mixed seating so early departures stay fueled and on schedule.
With meeting rooms, AV support, reliable Wi-Fi, and event parking, small trainings and briefings wrap up without unexpected slowdowns, and stay on schedule.
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
For a visit where an easy drive is key, Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area is a sensible base, making travel a manageable part of the day.
Lobby seating areas at Wingate by Wyndham balance lounge chairs and communal tables, offering guests versatile arrival spaces. All guest rooms highlight comfortable bedding, blackout shades, and quiet climate systems, reinforcing reliable rest across properties. Breakfast setups with cereals, coffee, and pastries provide guests with clarity and dependable routines each morning of their stay.
Business centers, breakfast service, and Wi-Fi join with meeting rooms and parking, supporting clarity for professionals on the road.
Ramada Hotel & Conference Center by Wyndham Edgewood
In the Chestertown area, Ramada Hotel & Conference Center by Wyndham Edgewood serves as a practical base, a spot that keeps travel easy.
Coffee stations in Ramada lobbies provide reliable care signals, offering guests refreshing touches that reinforce consistency. Guest rooms highlight plush bedding, blackout curtains, and climate systems, ensuring restful sleep and reliable comfort each night. Breakfast dining setups with cereals, fruit, and coffee provide clarity, making day-start routines simple across property locations.
Connectivity with Wi-Fi, breakfast setups, and vending options pairs with pools and parking, simplifying guest routines daily.
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
From Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG, Chester River Yacht & Country Club is within driving reach, a convenience that makes the hotel a strategic choice.
Hydration points with tea and coffee at Holiday Inn Express reinforce brand consistency, easing arrivals with simple courtesy touches. Guest rooms offer ergonomic desks, Wi-Fi, and USB charging, supporting both productivity and convenience for business travelers. Pools equipped with towel racks, loungers, and family seating add recreation spaces that balance relaxation with group activity.
Free Wi-Fi, complimentary breakfast, and fitness centers combine with indoor pools and business spaces, giving guests balanced routines.
Red Roof Inn Edgewood
This flexible location means Red Roof Inn Edgewood is a sensible base, letting guests travel to Chester River Yacht & Country Club with ease.
A consistent and friendly welcome from the staff makes any Red Roof Inn feel like a reliable and safe stop on a traveler's journey. All guest rooms provide a quiet, private space where travelers can decompress from the road and enjoy a peaceful night without disturbances. The free coffee service in the lobby is a consistent brand standard, offering a familiar comfort that loyal guests appreciate and expect.
With a seasonal pool for recreation, laundry for practicality, and free Wi-Fi for connection, the hotel covers all the travel basics.
Quality Inn & Suites Bel Air I-95 Exit 77A
Reaching Chester River Yacht & Country Club from Quality Inn & Suites Bel Air I-95 Exit 77A is a simple commute, a feature that allows guests to ease into their day's schedule.
Quality Inn arrival signage and staff presence help guests identify elevators, parking, and breakfast areas quickly, reducing backtracking. Guest rooms place outlets and USB charging near both beds and desks so devices top up overnight without interrupting sleep routines. Indoor pools and seasonal outdoor pools provide lap lanes, loungers, and towel pickup so quick swims slot neatly between meetings or sightseeing.
Mini-fridges, microwaves, and grab-and-go markets mean medication, snacks, and early breakfasts stay convenient without leaving the hotel footprint.
La Quinta Inn & Suites by Wyndham Bel Air / I-95 Exit 77A
Chester River Yacht & Country Club is an easy regional drive from La Quinta Inn & Suites by Wyndham Bel Air / I-95 Exit 77A, a layout that ensures travel logistics are never a concern.
La Quinta reception desks are designed with clear sightlines, ensuring guests immediately know where to check in upon entry. Guest rooms supply branded bath amenities, glass showers, and soft towels, refreshing personal routines with predictable clarity. Business spaces containing computers, Wi-Fi, and printers offer reliable support for professionals who need quick work solutions.
Meeting facilities, Wi-Fi, and breakfast service join with business centers and parking, supporting professional priorities easily.
Hampton Inn & Suites Edgewood / Aberdeen-South
When travel in the Chestertown area is a factor, Hampton Inn & Suites Edgewood / Aberdeen-South's position as a sensible base is a major benefit.
Lobby sofa clusters at Hampton Inn create regrouping areas, giving families comfortable zones to pause before heading to guest rooms. Each suite includes rainfall showers, premium toiletries, and soft towels, letting guests refresh comfortably after a day of activities. Breakfast nooks with fresh fruit, pastries, and self-serve coffee offer clarity at day’s start, supporting smooth and dependable routines.
Pet-friendly policies, complimentary internet, business spaces, laundry access, and hot breakfast bags keep travel flexible for families.
Book as a group & pay separately.
Lowest Group Rate Guaranteed.
Chester River Yacht & Country Club Local Area Guide
Welcome to the Chester River Yacht & Country Club, a premier destination for golf, dining, and community events on Maryland's Eastern Shore. This guide is designed for visiting golfers, families attending events, and anyone looking to explore the charming surroundings of Chestertown. You’ll find practical advice on navigating the club and its environs, from planning your arrival to discovering local dining and attractions that complement your visit. Let us help you make the most of your time here, ensuring a smooth and enjoyable experience whether you're here for a tournament, a casual round, or a special occasion.
Area contextNeighborhood Overview – Chester River Yacht & Country Club (Chestertown, MD)
Nestled on Maryland's Eastern Shore, the Chester River Yacht & Country Club is situated in a picturesque, semi-rural setting just a short drive from the historic town of Chestertown. The primary access route is via Quaker Neck Road, which connects to Maryland Route 20, leading towards the town and other regional highways. While the club itself offers ample on-site parking, those arriving from out of town will likely fly into Baltimore/Washington International Thurgood Marshall Airport (BWI), which is approximately a 70-mile drive. Driving times can vary significantly based on traffic, especially when approaching the Baltimore metropolitan area, so budgeting an extra 30-45 minutes for transit is wise. Public transportation options are limited in this more spread-out rural area; therefore, private vehicles or rideshare services are the most common ways to reach the club. For a smooth arrival, consider reaching the club at least 30-45 minutes before your tee time or event to allow for parking, check-in, and familiarization with the facilities, particularly during busy weekend periods or special events.
Lodging contextWhere to Stay Near Chester River Yacht & Country Club
Accommodations for visitors to the Chester River Yacht & Country Club are primarily found in the nearby historic town of Chestertown, offering a range of inns and bed & breakfasts that capture the area's colonial charm. While the club is a destination in itself, the closest cluster of hotels is concentrated within Chestertown, about a 10-15 minute drive away. Many visitors choose to stay in town to experience its shops and restaurants, then drive to the club for their activities. For those seeking more extensive hotel options, Salisbury is a larger city approximately an hour's drive south, offering a wider selection of national hotel chains. Due to the club's location, booking accommodations well in advance is highly recommended, especially during peak golf season (spring through fall) or around local festivals in Chestertown. Utilizing map filters that show proximity to Chestertown can help narrow down lodging choices that balance convenience to the club with access to town amenities. Consider properties that offer easy access to Route 20 for a straightforward commute to the golf course.
View nearby hotels Quick Plan EssentialsQuick-Plan Overview
- Baltimore/Washington International Thurgood Marshall Airport is about a 70-mile drive, taking roughly 1 hour and 15 minutes without traffic.
- Arrive 30-45 minutes prior to your tee time or event to allow for parking, check-in, and locker room access.
- Explore historic downtown Chestertown for unique shops, antique stores, and waterfront dining options after your visit.
- If weather is uncooperative, the historic taverns and cafes in Chestertown offer cozy indoor diversions.
- The club lounge or a casual restaurant in Chestertown serve as convenient spots for groups to gather post-activity.
Game Day Flow
Check-In & Warm-Up
Begin your day by arriving at the Chester River Yacht & Country Club at least 30-45 minutes before your scheduled tee time or event. This buffer allows ample time for parking, which is generally straightforward on-site, and proceeding to the pro shop or club office for check-in. Take advantage of the practice facilities, which typically include a driving range and putting green, to get a feel for the conditions and loosen up your swing. Familiarize yourself with the locker room amenities if needed, and then make your way to the first tee, ready to start your round or attend your event.
Mid-Day Regroup
After your initial activities, the club's facilities provide excellent opportunities for a mid-day regroup. If you've played a morning round, consider enjoying lunch at the club's restaurant or lounge, which offers a relaxed atmosphere and views of the course. This is an ideal time for players and their families to discuss the game, plan the rest of their day, or simply relax and refuel. For those attending an event, breaks might be structured, but the common areas of the club can serve as informal meeting points for attendees to connect and recharge between sessions or activities.
Wrap-Up & Departure
As your golf game concludes or your event winds down, take time to settle any outstanding balances at the pro shop or administrative office. If you’ve enjoyed your time, consider a final beverage at the club lounge or browse the pro shop for any merchandise. Plan your departure, considering potential travel times back to your accommodation or to your next destination, especially if heading towards major roadways. Ensure all personal belongings are gathered from the locker room and that your vehicle is easily accessible in the parking area for a smooth exit from the club grounds.
Things to Do Near Chester River Yacht & Country Club
Walkable
Chester River Yacht & Country Club Grounds
The club itself is a primary attraction, offering beautifully maintained grounds for a leisurely stroll or simply enjoying the natural surroundings. The meticulously kept golf course is the centerpiece, providing scenic vistas and a peaceful environment. Visitors can often find shaded benches or quiet spots to relax, particularly around the clubhouse and overlooking the water. It's an ideal place for quiet contemplation or enjoying the fresh air before or after scheduled activities. The marina facilities, if accessible, also offer a glimpse into local boating culture and water views.
On siteLocal Waterfront Views
While the club offers its own water views, a short drive into Chestertown provides access to the Chester River waterfront. Stroll along the docks and enjoy the picturesque scene of sailboats and yachts. The town's historic district lines the river, offering charming views of colonial architecture alongside the water. It's a peaceful area for a relaxing walk, especially in the late afternoon, where you can watch boats come and go and enjoy the tranquility of the river. The area is perfect for photography enthusiasts and those seeking a serene moment by the water.
Chestertown, MD · 2.5 mi5–15 Minutes Away
Historic Downtown Chestertown
Step back in time in Chestertown's beautifully preserved historic downtown, a designated National Historic Landmark District. Wander along High Street and Water Street, admiring the 18th-century architecture, charming boutiques, art galleries, and antique shops. The waterfront area is particularly scenic, offering views of the Chester River and its working harbor. Take your time exploring the unique shops, perhaps finding a local craft or antique treasure. The town offers a pleasant atmosphere for an afternoon of leisurely exploration and discovery, providing a stark contrast to the club's more focused activities.
Chestertown, MD · 2.5 miChesapeake Heritage Museum
Located in the heart of Chestertown, the Chesapeake Heritage Museum showcases the rich history and maritime heritage of the Chester River and the Eastern Shore. Housed in a historic building, the museum features exhibits on shipbuilding, oystering, and the area's colonial past. It offers a fascinating glimpse into the lives of the people who have shaped this region. The museum provides context for the local landscape and culture, making it a worthwhile stop for those interested in understanding the area's roots and development. Plan for about an hour to fully appreciate the displays.
Chestertown, MD · 2.8 miBeyond the Event: Beyond the immediate vicinity, the broader Eastern Shore offers numerous state parks and charming small towns, each with its own unique character. Consider a scenic drive to explore more of the rural landscapes, farms, and waterfront communities that define this part of Maryland. The natural beauty and slower pace of life are central to the Eastern Shore experience, inviting further exploration for those with extra time.
Dining & nightlifeFood & Drink Near Chester River Yacht & Country Club
Inside & Adjacent
CRYC Restaurant & Bar
The Chester River Yacht & Country Club features its own on-site dining establishment, offering a convenient and pleasant atmosphere for members and guests. The restaurant typically serves a menu that complements its setting, featuring American cuisine with potential seafood specialties reflecting its waterfront location. Enjoy meals with views of the golf course or marina, making it an ideal spot for a post-game meal or a relaxed lunch. The bar area provides a more casual setting for drinks and lighter fare, perfect for unwinding after a round or event.
On siteThe Kitchen at the Ebenezer Theater
Located within the historic Ebenezer Theater in downtown Chestertown, this restaurant offers a unique dining experience in a charming, revitalized space. The menu often focuses on fresh, seasonal ingredients, with creative American dishes and a well-curated wine list. Dining here combines culinary enjoyment with the ambiance of a historic venue, making it a popular choice for a special evening out. Reservations are often recommended, especially on weekends, to secure a table in this sought-after spot.
Chestertown, MD · 2.5 miNearby Gathering Spots
The Mainstay Inn & Conference Center Restaurant
The Mainstay Inn offers a refined dining experience in a beautifully restored historic inn located in downtown Chestertown. Their restaurant is known for its classic American cuisine, often featuring locally sourced ingredients, particularly seafood. It provides an elegant setting for dinner, suitable for couples or small groups seeking a more sophisticated meal. The inn also often hosts events and offers a cozy bar area for pre- or post-dinner drinks, contributing to its reputation as a local gathering place.
Chestertown, MD · 2.6 miBluebird Tavern
A popular spot in Chestertown for a more casual and lively atmosphere, the Bluebird Tavern serves up elevated pub fare and a good selection of craft beers and cocktails. It's a go-to for locals and visitors alike seeking a relaxed environment to enjoy good food and company. The menu typically includes well-crafted burgers, sandwiches, and shareable plates. The tavern often has a welcoming buzz, making it a great place to gather with friends or teammates after a day of activities.
Chestertown, MD · 2.7 miLocal & Elevated Picks
The Great Oak Grill
While a short drive, The Great Oak Grill in Georgetown offers a distinct dining experience, often focusing on seasonal menus with an emphasis on fresh, local ingredients and wood-fired cooking. The ambiance tends to be refined yet comfortable, making it a destination for those seeking a high-quality meal in a picturesque setting. It’s a good option for a more celebratory dinner or when you're looking to explore beyond the immediate Chestertown area for a culinary adventure.
Georgetown, MD · 9.5 miBad Habits Gastropub
For those willing to venture a bit further, Bad Habits Gastropub in Rock Hall provides a vibrant atmosphere and a creative take on comfort food, alongside an impressive craft beer selection. This spot is known for its inventive dishes and lively setting, appealing to groups looking for a fun and casual dining experience. It’s a great example of the diverse culinary offerings available on the Eastern Shore, rewarding those who explore its coastal towns.
Rock Hall, MD · 15.0 miLocal Tips & Year-Round Info
- Weekends, especially during event season, can see increased traffic on Route 20 heading into Chestertown from the club.
- Most dining establishments in Chestertown observe standard business hours, with some smaller shops closing on Mondays.
- Parking in downtown Chestertown is generally ample, particularly in designated public lots, though street parking is metered.
- The Eastern Shore experiences a slower pace of life; embrace it and allow extra time for your journeys.
- Consider checking local event listings in Chestertown for festivals or markets that might coincide with your visit.
Weather & Seasons at Chester River Yacht & Country Club
- Winter: Winters here are cool to cold, with average temperatures ranging from the low 30s to the mid-40s Fahrenheit. Expect rain and occasional snow or sleet, which can impact course conditions and outdoor activities. Dressing in warm layers, including waterproof outerwear, is essential for comfort. Shorter daylight hours mean planning activities for mid-day is advisable.
- Spring & early summer: Spring brings milder temperatures, typically from the 50s to the 70s, with increasing sunshine but also a chance of rain showers. Early summer continues this trend before temperatures climb. It's an excellent time for golf and outdoor exploration, with blooming landscapes. Light jackets or sweaters are useful for cooler mornings and evenings.
- Mid-summer: Mid-summer is characterized by warm to hot and humid conditions, with average highs in the upper 80s and occasional heatwaves pushing into the 90s. Afternoon thunderstorms are common. Lightweight, breathable clothing is a must, along with sun protection like hats and sunscreen. Hydration is key for any outdoor activities during this period.
- Fall season: Fall offers crisp and pleasant weather, with temperatures gradually cooling from the 70s into the 50s. This season is renowned for its beautiful autumn foliage, making it a visually stunning time to visit. Layers are recommended, as mornings can be cool and afternoons mild. It’s a prime time for golf and enjoying the scenic beauty before winter sets in.
- Rain & snow: Rain is a frequent occurrence throughout the year, especially in spring and fall. Winters can bring snow, sleet, and freezing rain, potentially leading to course closures or hazardous driving conditions. Always check local weather forecasts before traveling and be prepared with waterproof gear. Even summer thunderstorms can be intense but are often short-lived.
Venue Facts & Trip Essentials
Venue facts
- Primary team: N/A (Golf Club/Social Venue)
- Neighborhood: Rural Chester River Area
- Nearest airport: BWI Airport (Baltimore)
- Parking: Ample on-site parking
- Walkable district: Chestertown Historic District
Trip essentials
- Groceries & supplies: Stores in Chestertown
- Pharmacy: CVS in Chestertown
- Urgent care: University of Maryland Shore Emergency Center at Easton (approx. 30 min drive)
- Downtime: Historic Chestertown cafes and riverfront
- Pro tip: Book tee times and dining well in advance, especially during peak season.

