Hotels in Chestertown, MD - Best Chestertown Hotels from £37 - Fully Refundable Options

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

£82

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a sofa, two beds, a painting, and a lamp.

A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Chestertown

Kate

£60

includes taxes & fees

18 Oct - 19 Oct

A row of motel rooms with stone walls and red doors.

A living room with a wooden cabinet, a television, a sofa, and a dining table.

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Chestertown

Kathy

£53

includes taxes & fees

13 Oct - 14 Oct

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

A campfire in a stone fire pit by a lakeside at sunset.

4. The Lodge at Great Oak Landing

Chestertown

Sandra

£93

includes taxes & fees

14 Oct - 15 Oct

A two-story house with a covered porch, a staircase, and a garden area.

A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

A row of stationary bicycles with green frames and white seats, parked outdoors.

5. Haven Point Inn and Gallery

Rock Hall

Joe

£112

includes taxes & fees

13 Oct - 14 Oct

A boat deck with a white bench and a view of a calm lake and distant trees.

A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

A buffet with various food items including fruits, pastries, and salads.

A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

6. Inn at Huntingfield Creek

Rock Hall

Christine

£134

includes taxes & fees

1 Nov - 2 Nov

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A modern food court with a central island, various food stations, and a yogurt display.

A reception desk with a modern design, a digital display, and a check-in counter.

7. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

£90

includes taxes & fees

9 Nov - 10 Nov

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

An outdoor event area with round tables and a view of the water.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

8. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

£127

includes taxes & fees

18 Oct - 19 Oct

A large, two-story barn-style building with a covered front porch and a garage.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

9. Kent Island Resort

Stevensville

Bethany

£126

includes taxes & fees

28 Oct - 29 Oct

A patio with outdoor seating, overlooking a marina with boats.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

An indoor swimming pool with clear views of boats and water.

10. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

£116

includes taxes & fees

19 Oct - 20 Oct

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

A spacious lobby with a staircase, a reception desk, and a dining area.

11. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

£76

includes taxes & fees

8 Nov - 9 Nov

A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

A hotel with a modern facade, a covered entrance, and a red car parked outside.

A modern lobby with a bar area, seating arrangements, and a television screen.

An outdoor patio with brick walls, green chairs, and a fire pit.

12. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

Juanita

£93

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk, a chair, and a bathroom.

A wooden pavilion with picnic tables and benches, a grill, and a red bench.

A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.

13. Best Western Kent Narrows Inn

Grasonville

Wesley

£75

includes taxes & fees

8 Nov - 9 Nov

A modern hotel lobby with a long dining table, several chairs, and a bar area.

A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

14. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

Lyn

£72

includes taxes & fees

2 Nov - 3 Nov

A hotel entrance with a clear sign reading "LA QUINTA".

A vending area with two beverage dispensers, a wall-mounted display of personal care items, and shelves stocked with snacks and beverages.

A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.

A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.

15. La Quinta Inn & Suites by Wyndham Aberdeen-APG

Aberdeen

robin

£91

includes taxes & fees

13 Oct - 14 Oct

A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

A vending machine with snacks and a drink dispenser.

A hotel room with a sofa, a bed, a desk, and a lamp.

A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

16. Quality Inn & Suites Bel Air I-95 Exit 77A

Edgewood

Jose

£52

includes taxes & fees

27 Oct - 28 Oct

A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.

An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.

A home gym with an elliptical, a treadmill, and a stationary bike.

17. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

Robert

£70

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

18. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Bel Air

Vanessa

£75

includes taxes & fees

1 Nov - 2 Nov

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

19. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

£190

includes taxes & fees

2 Nov - 3 Nov

A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

A modern building with a stone facade, large windows, and outdoor seating area with chairs.

A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.

20. Hilton Garden Inn Bel Air

Bel Air

Jaccilynne

£89

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)

Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.

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Chestertown Historic District

This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick pavements along the Chester River or visit during the annual Tea Party Festival reenactments.

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River Arts Chestertown

7.4/10 (6 reviews)

Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.

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Historical Society of Kent County Maryland

7.4/10 (6 reviews)

Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life.

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Crumpton Auction

8.8/10 (3 reviews)

Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins.

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Wilmer Park

8.2/10 (13 reviews)

Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts.

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Kings Town Park

Kings Town Park offers serene pathways winding through lush greenery in Chestertown, Maryland. Enjoy morning strolls or invigorating runs along the scenic trails away from urban bustle.

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Sumner Hall

You can spend time exploring the galleries in Sumner Hall during your travels in Chestertown. Experience the area's festivals and art scene.

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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

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A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent

"The room was clean, staff was helpful for the most part with a few exceptions, wasn’t able to get breakfast because the lady snatched everything up quickly even after seeing me wait for someone to finish making their waffles,and wasn’t many options for breakfast anyways"

The Lodge at Great Oak Landing

10/10 Excellent

"Stayed in October. Room was clean and had a great view of the water. No microwave or coffee in the room but it was always available at the end of the hall. Keyless entry was convenient . Cell service is terrible though had to go to the windows to have any service."

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent

"Little weird driveway"

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent

"This is like our home away from home when visiting our son at college."

Hampton Inn Baltimore/Glen Burnie

8/10 Good

"A good location. Many stores and restaurants within walking distance and many more a short drive away."

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"Had an amazing stay here. The room was spotlessly clean from top to bottom. The linens were fresh, the bathroom was pristine, and everything felt completely sanitized. It’s rare to find a property that pays such close attention to detail. Fantastic housekeeping service!"

Pendry Baltimore

8/10 Good

"Beautiful Room"

Hampton Inn Baltimore/White Marsh

8/10 Good

"good"

More cheap stays in Chestertown

Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road Edgewood MD

£52

27 Oct - 28 Oct

includes taxes & fees

7.4/10 Good! (1,221 reviews)

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

£60

18 Oct - 19 Oct

includes taxes & fees

Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

£72

2 Nov - 3 Nov

includes taxes & fees

Hampton Inn Baltimore/White Marsh

8225 Town Center Drive Baltimore MD

£89

18 Oct - 19 Oct

includes taxes & fees

7.8/10 Good! (1,003 reviews)

SpringHill Suites Baltimore White Marsh/Middle River

6110 Greenleigh Avenue Middle River MD

£93

18 Oct - 19 Oct

includes taxes & fees

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

£98

18 Oct - 19 Oct

includes taxes & fees

Find out more about Chestertown

Top reasons to visit Chestertown

Historic Charm: Stroll through the picturesque streets of historic Chestertown, rich in heritage and character.
Outdoor Activities: Enjoy a variety of outdoor pursuits, from nature walks to beach outings along the scenic Eastern Shore.
Family-Friendly Attractions: Discover numerous attractions suitable for families, ensuring entertainment for all ages.
Welcoming Community: Experience the warm and friendly atmosphere of Chestertown, making you feel right at home.
Diverse Accommodation: Choose from a range of lodging options, including pet-friendly and LGBTQIA-friendly establishments.

Find great hotels near Chestertown

Discover a charming selection of hotels and motels in Chestertown, Maryland, tailored to meet the diverse needs of every traveller. Whether you're seeking pet-friendly accommodations, facilities for business travel, or a welcoming environment for the LGBTQIA community, you'll find the perfect spot to relax and unwind. Explore the best lodging options near Chestertown and enjoy a delightful stay in this picturesque town.

Quality Inn & Suites Bel Air I-95 Exit 77A: This budget-friendly hotel provides a convenient lodging option for business travellers seeking comfort and accessibility. Located 33.8km from Chestertown, Quality Inn & Suites Bel Air offers essential amenities designed for a productive stay. Guests can enjoy complimentary breakfast, free Wi-Fi, and a well-equipped business centre. The hotel's straightforward approach combines practicality with affordability, ensuring a pleasant experience for those on work-related visits.
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: With a commendable guest rating of 8.2, this welcoming hotel caters particularly well to pet owners. Situated 33.8km from Chestertown, La Quinta Inn & Suites is a pet-friendly haven, allowing guests to bring their furry companions along for the adventure. The amenities include a complimentary breakfast, fitness centre, and free Wi-Fi. Its warm atmosphere and accommodating pet policies make it an ideal choice for travellers looking to explore the area with their pets.
Americas Best Value Inn Edgewood: Another budget-friendly option, Americas Best Value Inn Edgewood is perfect for travellers with pets, allowing dogs and cats on the premises. Located 33.8km from Chestertown, the hotel features comfortable accommodations and essential amenities, including free Wi-Fi and on-site parking. The flexible pet policy, which includes a variable fee, makes it easy for pet owners to enjoy their stay. This property offers a relaxed environment that prioritises both comfort and affordability.

Where to stay in and around Chestertown

Chestertown, Maryland, is a delightful blend of history and natural beauty, perfect for a relaxing getaway. Explore the charming streets of historic Chestertown, where family-friendly attractions abound. The Eastern Shore offers tranquil scenery, ideal for outdoor enthusiasts. Venture into nearby towns to experience a warm, welcoming atmosphere and budget-friendly options, making it an ideal destination for a peaceful retreat. Enjoy the local culture and the friendly people that make this region truly special.

Worton: Situated a mere 6.4km from Chestertown, Worton offers a charming blend of outdoor adventures and picturesque scenery. Visitors flock here during the peak months of April to May and July, drawn by its recreational areas and stunning natural landscapes. Whether you fancy a day at the beach, a stroll by the bay, or a serene afternoon by the lake, Worton provides a wealth of options for relaxation and exploration. With its seasonal visitor trends, it’s the perfect getaway for nature enthusiasts looking to unwind in a tranquil setting.
Georgetown: Nestled conveniently within the Chestertown area, Georgetown is a quaint village that attracts visitors primarily from June to August. Known for its romantic atmosphere and entertainment offerings, this village boasts a recreation centre and scenic hiking trails that cater to outdoor lovers. The nearby beach and marina offer splendid opportunities for water activities, while the proximity to a national state park allows for further exploration of Maryland's natural beauty. Georgetown is an ideal stop for those seeking both adventure and relaxation in a charming small-town setting.
Pomona: A delightful village located close to Chestertown, Pomona welcomes travellers year-round, with a slight peak in visitor numbers during the summer months of June to August. Known for its family-friendly atmosphere, Pomona features a shopping centre and golf facilities that cater to a variety of interests. The local parks and nearby beach provide ample space for outdoor activities, making it a great destination for families looking to enjoy quality time together. With its accessible amenities and relaxed vibe, Pomona is perfect for those seeking a leisurely escape.

Things to do in Chestertown

Chestertown offers a delightful escape for those seeking outdoor adventures and scenic beauty. Visitors can enjoy a variety of activities, from educational experiences to motor racing events, making it an ideal destination for both relaxation and excitement. The town's charm and natural surroundings provide a perfect backdrop for a memorable holiday.

Shopping

In Chestertown, visit local shops like the Imperial Hotel Gift Shop for unique souvenirs and artisan goods. If you're up for a drive, head to the nearby Annapolis Mall, around 48.3km away, boasting a wide selection of national retailers and dining options for a full shopping day.

Recreation

Serenity Spa offers a tranquil environment with soothing treatments, including massages and facials, perfect for rejuvenation. For outdoor relaxation, visit Wilmer Park, featuring scenic views, walking paths, and picnic areas, ideal for unwinding amidst nature's beauty.

Adventure

In Chestertown, explore the scenic Chester River by kayaking or paddleboarding, offering a thrilling way to experience the area's natural beauty. For a unique adventure, try the local bike trails that wind through picturesque landscapes, perfect for enjoying the fresh air and charming surroundings.

Nightlife

Chestertown offers a charming nightlife with venues like the historic Garfield Centre for the Arts, hosting live performances, and the relaxed atmosphere at the Fish Whistle, perfect for unwinding with local brews. For a lively evening, explore the vibrant local bars along High Street.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chestertown

The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, favoured location, and the type of hotel you desire. To discover the best prices and deals, simply sort the price filter from lowest to highest.
Consider bundling your trip: You can save money by combining your hotel stay in Chestertown with your flights and activities by booking a package through Expedia.

Find the best attractions in Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor activities, scenic views, and family-friendly experiences. Visitors can explore urban parks, marinas, and the charming historic district. The area is perfect for those seeking beach outings and nature walks, making it an ideal destination for a relaxing vacation. Don't miss the opportunity to visit historic Chestertown for a taste of its rich heritage.

Historical Society of Kent County Maryland: Discover the rich heritage of the region at this engaging museum. With various exhibits and historical artefacts, it offers a fascinating glimpse into Kent County's past, making it a must-visit for history enthusiasts.
Wilmer Park: This charming urban park is perfect for family outings and leisurely strolls. Enjoy its scenic views, playgrounds, and picnic areas, providing a delightful space to relax amidst nature in the heart of Chestertown.
River Arts Chestertown: Immerse yourself in the vibrant local arts scene at this arts centre. Featuring diverse exhibitions and workshops, it showcases the creativity of local artists and offers a platform for cultural engagement.

Best time to go to Chestertown

The best time to visit Chestertown can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chestertown falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chestertown falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	77.4°F (25.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Average	Average
September	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Average	Average
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

The nearest major airports for your trip to Chestertown

When planning your visit to Chestertown, Maryland, you have several airports to consider. Philadelphia International Airport (PHL) is approximately 101.4km away, with luxury accommodation options such as the W Philadelphia and The Rittenhouse, both within 9.7km of the airport. Alternatively, Ronald Reagan Washington National Airport (DCA) is 93.3km away, offering nearby hotels like the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both just 3.2km distant. Lastly, Washington Dulles International Airport (IAD) is 122.3km away, with convenient stays at The Westin Washington Dulles Airport and Hyatt Regency Dulles International Airport, both a mile from the terminal.

Frequently asked questions

What is the best area to stay in Chestertown?

The best area to stay in Chestertown is the historic downtown, particularly around High Street and Water Street.This charming area is the heart of Chestertown, known for its beautifully preserved 18th-century architecture and tree-lined streets. It's very walkable, with most shops, restaurants, and attractions clustered around the main thoroughfares. The Chestertown Marina and the scenic waterfront along the Chester River are also just a short stroll away.For couples looking for a romantic getaway, staying in downtown Chestertown offers a delightful experience. You'll find boutique hotels and historic inns that provide a cosy base, with easy access to art galleries, antique shops, and fine dining. Enjoy an evening walk along the waterfront or catch a performance at the local theatre.Solo travellers will also appreciate the convenience and character of downtown. Everything you need is within walking distance, from independent bookstores to coffee shops, making it easy to explore at your own pace and connect with the local community.

What are the best hotels in Chestertown that travellers recommend?

Two of the best hotels in Chestertown that receive consistently high recommendations from travellers are the Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.The Comfort Inn & Suites Chestertown, with an 8.6 rating, is frequently praised by guests for its comfortable and clean rooms and beds. Travellers also highlight the friendly and helpful staff, particularly at the front desk, and the nice, free breakfast.Another highly recommended option is the 3.5-star The Lodge at Great Oak Landing, which has an 8.0 rating. Guests often comment on the friendly and helpful staff, the excellent food at the on-site restaurant, and the perfect, comfortable rooms. This hotel also features an on-site golf course, water and marina views, and a great pool area with umbrellas and sun loungers.

What are the best family hotels in Chestertown?

For family-friendly accommodation in Chestertown, the Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing are both excellent choices.The Comfort Inn & Suites Chestertown, with an 8.6 rating, is highly regarded by guests for its comfortable and clean rooms, as well as its friendly and helpful staff. The hotel offers a pool, sofa beds, and cribs, suiting families. Guests also appreciate the complimentary and nice breakfast provided.Another great option is the 3.5-star Lodge at Great Oak Landing, which has an 8.0 rating. This hotel features a pool, connecting rooms, and a playground for children, making it very suitable for families. Guests consistently praise the friendly and helpful staff, the great restaurant with excellent food, and the comfortable rooms. The property also boasts water and marina views, along with pool umbrellas and sun loungers for relaxation.

What hotels in Chestertown offer free breakfast?

For hotels in Chestertown that offer complimentary breakfast, the Comfort Inn & Suites Chestertown is an excellent choice.This highly-rated hotel, with an 8.6 review score, provides a free full breakfast, which guests often describe as nice. It also offers other convenient amenities such as free internet, complimentary WiFi, and free self-parking. Guests consistently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff. The hotel is conveniently located just 1.1 kilometres from Chestertown Dog Park and Rolling Road Park.

What are the top pet-friendly hotels in Chestertown?

For top pet-friendly hotels in Chestertown, consider the Comfort Inn & Suites Chestertown, the Red Roof Inn & Suites Chestertown, and the Driftwood Inn.The Comfort Inn & Suites Chestertown, with an 8.6 rating, is a highly recommended 3-star option. This hotel permits pets and offers early check-in, free breakfast, and free full breakfast. Guests frequently mention the comfortable and clean rooms, the friendly and helpful staff, and the comfortable beds. It is conveniently located near Chestertown Dog Park and Rolling Road Park, both just 1.1 km away.Another great choice is the Red Roof Inn & Suites Chestertown, rated 7.2. This hotel also permits pets, including both dogs and cats. Guests have praised the comfortable and clean rooms, the nice staff, and the easy parking. It is within 1 km of Chestertown Dog Park and Rolling Road Park.The Driftwood Inn is another pet-friendly option, providing free toiletries, free self-parking, and free WiFi. Guests often highlight the clean rooms and friendly staff. It is well-situated for exploring local arts and nature, being 1.6 km from the Garfield Centre for the Arts at the Prince Theater, 1.5 km from River Arts Chestertown, and 2.0 km from Wilmer Park.

What are the best budget hotels in Chestertown?

For budget hotels in Chestertown, Maryland, the Comfort Inn & Suites Chestertown and the Red Roof Inn & Suites Chestertown are both good options.The Comfort Inn & Suites Chestertown, with an 8.6 rating, offers comfortable and clean rooms with free WiFi and toiletries. Guests consistently praise the friendly and helpful staff, as well as the nice complimentary breakfast. It is conveniently located near Chestertown Dog Park and Rolling Road Park, both just over 1 km away.Another suitable choice is the Red Roof Inn & Suites Chestertown, rated 7.2. This hotel also provides comfortable and clean rooms, free WiFi, and complimentary toiletries. Guests often mention the friendly staff and easy parking. It is situated approximately 1 km from Chestertown Dog Park and Rolling Road Park.

What are the most romantic hotels in Chestertown for couples?

For couples seeking a romantic getaway in Chestertown, The Lodge at Great Oak Landing is a highly recommended choice.This 3.5-star lodge, with a rating of 8.0, offers a delightful setting with many rooms providing marina and water views, great for a romantic stay. Guests frequently praise the friendly and helpful staff, as well as the excellent food served at the on-site restaurant. The comfortable rooms also contribute to a great experience. The property features a shared, secured pool with umbrellas and sun loungers, and some rooms include a furnished balcony, ideal for enjoying the picturesque surroundings together.

What are the best hotels in Chestertown near Wilmer Park?

For a family-friendly accommodation near Wilmer Park in Chestertown, the Driftwood Inn is a suitable option.The Driftwood Inn offers child-friendly window designs, ensuring a safe stay for families. Guests appreciate the complimentary toiletries, free self-parking, and free WiFi access. It is located 2.0 km from Wilmer Park, making it a convenient choice for those wishing to visit the park. Guests consistently praise the clean rooms and friendly staff.

When is the best time to go to Chestertown?

The best time to go to Chestertown is during the spring (April to May) and autumn (September to October) months when the weather is pleasant and the town hosts various events.Spring offers mild temperatures, making it ideal for exploring the historic streets and enjoying outdoor activities along the Chester River. The Chestertown Tea Party Festival in May is a popular annual event, reenacting the 1774 protest and featuring a parade, historic crafts, and tall ship tours. This period is particularly good for families looking for engaging historical experiences.Autumn brings cooler weather and beautiful fall foliage, especially along the riverfront and surrounding countryside. The Chestertown Harry Potter Festival in September draws many visitors with themed activities, street performers, and a "Quidditch" tournament.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chestertown.

How much is the nightly rate at a Chestertown hotel?

Prices for hotels in Chestertown often vary, but you can find a great deal from £37 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Wye Mills Holiday Rentals

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Our top choices for Chestertown hotels

1. Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

3. Driftwood Inn

4. The Lodge at Great Oak Landing

5. Haven Point Inn and Gallery

6. Inn at Huntingfield Creek

7. Holiday Inn Express Annapolis East-Kent Island by IHG

8. Hyatt Place Kent Narrows & Marina

9. Kent Island Resort

10. Hilton Garden Inn Kent Island Marina

11. Quality Inn Grasonville near Kent Island

12. SpringHill Suites Baltimore White Marsh/Middle River

13. Best Western Kent Narrows Inn

14. Hampton Inn & Suites Edgewood/Aberdeen-South

15. La Quinta Inn & Suites by Wyndham Aberdeen-APG

16. Quality Inn & Suites Bel Air I-95 Exit 77A

17. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

18. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

19. The Inn at Chesapeake Bay Beach Club

20. Hilton Garden Inn Bel Air

Stay near popular Chestertown attractions

Washington College

Chestertown Historic District

River Arts Chestertown

Historical Society of Kent County Maryland

Crumpton Auction

Wilmer Park

Kings Town Park

Sumner Hall

Learn more about Chestertown

Top Chestertown Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

The Lodge at Great Oak Landing

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Fairfield Inn & Suites by Marriott White Marsh

Hampton Inn Baltimore/Glen Burnie

The Inn at Chesapeake Bay Beach Club

Pendry Baltimore

Hampton Inn Baltimore/White Marsh

More cheap stays in Chestertown

Quality Inn & Suites Bel Air I-95 Exit 77A

Red Roof Inn & Suites Chestertown

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn Baltimore/White Marsh

SpringHill Suites Baltimore White Marsh/Middle River

Best Western Plus Hotel & Conference Center

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Top reasons to visit Chestertown

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Where to stay in and around Chestertown

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