𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chestertown from RM288 (2026) - 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 gym with various exercise equipment, a television, and a clock on the wall.

Two front-loading washing machines in a laundry room with a beige wall and a white ceiling.

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

RM415

RM460 total

includes taxes & fees

1 Nov - 2 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 multi-story brick building with a covered entrance and a parking lot.

A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Chestertown

Linda

RM294

RM326 total

includes taxes & fees

11 Oct - 12 Oct

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

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

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

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

3. Driftwood Inn

Chestertown

Kathy

RM259

RM288 total

includes taxes & fees

5 Oct - 6 Oct

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

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

A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

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.

4. The Lodge at Great Oak Landing

Chestertown

Sandra

RM441

RM504 total

includes taxes & fees

7 Oct - 8 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

RM546

RM606 total

includes taxes & fees

6 Oct - 7 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 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.

A sunflower field with a white barn and a large house in the background.

6. Inn at Huntingfield Creek

Rock Hall

Christine

RM655

RM727 total

includes taxes & fees

1 Nov - 2 Nov

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

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

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

7. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

RM621

RM689 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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.

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

Grasonville

Marc

RM421

RM467 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

9. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

Evelyn

RM437

RM505 total

includes taxes & fees

8 Oct - 9 Oct

A modern building with a patio area featuring outdoor seating and a fire pit.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.

10. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

RM486

RM540 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

11. Hilton Garden Inn Kent Island Marina

Grasonville

roney

RM566

RM628 total

includes taxes & fees

19 Oct - 20 Oct

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

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

A gym with treadmills, elliptical machines, and a weight machine.

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

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

Bel Air

Vanessa

RM364

RM408 total

includes taxes & fees

1 Nov - 2 Nov

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

A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

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

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

13. Hilton Garden Inn Bel Air

Bel Air

Jaccilynne

RM448

RM502 total

includes taxes & fees

3 Nov - 4 Nov

A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

A formal dining room with a long table, chairs, a chandelier, and a fireplace.

A cozy living room with a sofa, armchair, and a fireplace.

A traditional house with a covered porch, white picket fence, and lush greenery.

14. Vandiver Inn

Havre De Grace

Mary

RM714

RM800 total

includes taxes & fees

7 Oct - 8 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.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

15. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

RM392

RM435 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

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.

16. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

Lyn

RM348

RM390 total

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 bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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

17. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

RM781

RM971 total

includes taxes & fees

19 Oct - 20 Oct

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

A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.

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

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

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

Edgewood

Dalton

RM339

RM380 total

includes taxes & fees

3 Nov - 4 Nov

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

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 hotel lobby with seating areas, a TV on the wall, and patterned curtains.

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

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

Aberdeen

robin

RM413

RM463 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

A lobby with a beige carpet, a reception desk, and two beige armchairs.

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

Edgewood

Cherrie Mae

RM260

RM291 total

includes taxes & fees

14 Oct - 15 Oct

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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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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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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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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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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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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)

This historic 1928 theatre offers an intimate setting for plays, music, and lectures in city centre Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening.

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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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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.

See all hotels in Chestertown

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

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent

"Our room was a little dated and worn, but had all the amenities we care about - comfy bed, good shower, nice towels - and was clean and quiet. Affordable and convenient to highway and shopping, with friendly helpful staff."

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

8/10 Good

"Hotel was nice, pool was closed, the bathroom door didn't close properly and needs to be fixed. Staff was SUPER NICE and very helpful. Overall you pay for the location, which is very convenient."

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

8/10 Good

"The room itself was rather clean. The few members of staff I spoke to were helpful. The breakfast offered was okay, though when I went I believe the batter was out. No one's fault just poor planning on my part. Overall a good stay for the price."

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

8/10 Good

"ok"

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"Had a good time. Nice area"

The Lodge at Great Oak Landing

10/10 Excellent

"This is a wonderful facility for a couple or family. The restaurant is just "ok"."

More cheap stays in Chestertown

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

2112a Emmorton Park Road Edgewood MD

RM260

RM291 total

14 Oct - 15 Oct

includes taxes & fees

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

RM294

RM326 total

11 Oct - 12 Oct

includes taxes & fees

7.2/10 Good! (504 reviews)

Hampton Inn & Suites Edgewood/Aberdeen-South

2110 Emmorton Park Rd Edgewood MD

RM348

RM390 total

1 Nov - 2 Nov

includes taxes & fees

Hampton Inn Baltimore/White Marsh

8225 Town Center Drive Baltimore MD

RM415

RM480 total

12 Oct - 13 Oct

includes taxes & fees

SpringHill Suites Baltimore White Marsh/Middle River

6110 Greenleigh Avenue Middle River MD

RM437

RM505 total

8 Oct - 9 Oct

includes taxes & fees

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD

RM473

RM555 total

11 Oct - 12 Oct

includes taxes & fees

Frequently asked questions

Where is the best place for a stay in Chestertown?

Based on our traveller data, Red Roof Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free parking and free WiFi. Other good options for your trip include The Lodge at Great Oak Landing and Comfort Inn & Suites Chestertown. See all available top hotels, or vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

What's the best family accommodation in Chestertown?

Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it's a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What is the top LGBTQ-friendly hotel in Chestertown?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown are two other good options for your stay. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best dog-friendly accommodation option in Chestertown?

Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Other good options for you and your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn. See more pet-friendly hotel accommodations in Chestertown.

What's the best hotel to stay near the beach in Chestertown?

The Lodge at Great Oak Landing is a top lodge with 2 restaurants and a seasonal outdoor pool, and it's located near a private beach . Great Oak Manor is another good option to stay near the beach. See more stays near the beach in Chestertown.

What are some accommodation options with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 2 restaurants and 2 bars/lounges. View all hotels with pools in Chestertown.

How is it to stay in Chestertown?

Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 45 hotels and other accommodation options to choose from. Find out more about Chestertown.

What should I see while I'm in Chestertown?

Cultural venues include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. Take a look at what more there is to see and do in Expedia's Chestertown guide.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

Chestertown hotels from RM288

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chestertown

Check prices for these dates

Filter by

Star rating

Guest rating

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. Hyatt Place Kent Narrows & Marina

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

9. SpringHill Suites Baltimore White Marsh/Middle River

10. Fairfield Inn & Suites by Marriott Middletown

11. Hilton Garden Inn Kent Island Marina

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

13. Hilton Garden Inn Bel Air

14. Vandiver Inn

15. Quality Inn Grasonville near Kent Island

16. Hampton Inn & Suites Edgewood/Aberdeen-South

17. The Inn at Chesapeake Bay Beach Club

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

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

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

Stay near popular Chestertown attractions

Washington College

River Arts Chestertown

Chestertown Historic District

Historical Society of Kent County Maryland

Wilmer Park

Kings Town Park

Garfield Center for the Arts at the Prince Theater

Crumpton Auction

Learn more about Chestertown

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

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

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

Hilton Garden Inn Kent Island Marina

The Lodge at Great Oak Landing

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

Frequently asked questions

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