Chestertown hotels from RM231

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29 Dec - 30 Dec
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30 Dec - 31 Dec
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2 Jan - 4 Jan
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9 Jan - 11 Jan

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Our top choices for Chestertown hotels

Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is RM401
RM458 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Lodge at Great Oak Landing
Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (423)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is RM292
RM324 total
includes taxes & fees
4 Jan - 5 Jan 2026
Red Roof Inn & Suites Chestertown
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (861)
"Everything was well!"
United States
Ahmed
The price is RM404
RM449 total
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Chestertown
Terrace/patio
Vandiver Inn

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (533)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn
In-room safe, desk, soundproofing, rollaway beds
Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (969)
"It's was satisfactory "
United States
John
The price is RM215
RM241 total
includes taxes & fees
4 Jan - 5 Jan 2026
Super 8 by Wyndham Havre De Grace Aberdeen Area
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (683)
"friendly staff, clean room / lobby, nice bar, everything was great"
United States
William
The price is RM470
RM522 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (97)
"Spotless, very good "
United States
Efrain
The price is RM441
RM494 total
includes taxes & fees
30 Dec - 31 Dec
TownePlace Suites by Marriott Edgewood Aberdeen
In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is RM341
RM378 total
includes taxes & fees
2 Jan - 3 Jan 2026
Quality Inn Grasonville near Kent Island
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is RM518
RM717 total
includes taxes & fees
1 Jan - 2 Jan 2026
Kent Island Resort
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (942)
"It was very comfortable and clean"
United States
Maria
The price is RM320
RM355 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is RM668
RM845 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Chesapeake Bay Beach Club
Exterior
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very good, (474)
"The staff is great, roon clean & spacious"
United States
Thomas
The price is RM336
RM377 total
includes taxes & fees
31 Dec - 1 Jan 2026
Candlewood Suites Aberdeen-Bel Air by IHG
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (234)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is RM395
RM443 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Bel Air
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1002)
"Nice place "
United States
Tucker T
The price is RM338
RM375 total
includes taxes & fees
5 Jan - 6 Jan 2026
Best Western Kent Narrows Inn
Property amenity
SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (364)
"I usually like staying at SpringHill Suites locations. While this location was absolutely clean, quiet and the staff was great, the facility itself was a bit run down- cracks in the sink, etc. "
United States
Katharine
The price is RM446
RM499 total
includes taxes & fees
5 Jan - 6 Jan 2026
SpringHill Suites by Marriott Edgewood/Aberdeen
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.4 out of 10, (416)
"The hotel was great the staff was great very clean "
United States
Sean
The price is RM263
RM304 total
includes taxes & fees
5 Jan - 6 Jan 2026
Super 8 by Wyndham Baltimore/Essex Area
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1002)
"Clean and friendly staff"
United States
Lisa
The price is RM495
RM549 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Kent Island Marina
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (219)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is RM341
RM382 total
includes taxes & fees
15 Jan - 16 Jan 2026
Courtyard Aberdeen at Ripken Stadium
Lobby
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (304)
"Always consistent and great staff!"
United States
Linda
The price is RM441
RM494 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Aberdeen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Chestertown attractions

Washington College

4.1/5 (45 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.
See properties

Historical Society of Kent County Maryland

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.
See properties

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
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Staff was extremely courteous and helpful. Breakfast was great. The room was very clean. The pool was well maintained. It was a great hotel all around."
Richard 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

More cheap stays in Chestertown

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

1709 Edgewood Road Edgewood MD
The price is RM207 per night from 30 Dec to 31 Dec
RM207
RM231 total
30 Dec - 31 Dec
includes taxes & fees
5.6/10 (999 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Reviews from our site also recommend The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your stay. 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?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing 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 a seasonal outdoor pool and 3 bars/lounges, and it's located near a private 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, 3 bars/lounges and free WiFi. 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 39 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. 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.

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