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Chestertown hotels from RM235

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Check prices for these dates

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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Star rating

Our top choices for Chestertown hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (929 reviews)
"Great visit"
United States
Danielle
The price is RM437
RM486 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (89 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is RM540
RM617 total
includes taxes & fees
6 Jul - 7 Jul
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (458 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is RM294
RM326 total
includes taxes & fees
9 Jul - 10 Jul
Red Roof Inn & Suites Chestertown
Front of property ā€“ evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didnā€™t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didnā€™t care what they were doing. Donā€™t go to this place it should be shut down !"
United States
Gabriel
The price is RM259
RM288 total
includes taxes & fees
7 Jul - 8 Jul
Driftwood Inn
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (612 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is RM385
RM431 total
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,003 reviews)
"Good hotel for the price"
United States
Brenda
The price is RM511
RM567 total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn
Lobby

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,006 reviews)
"We had a very nice stay."
United States
Aimee
The price is RM390
RM437 total
includes taxes & fees
6 Jul - 7 Jul
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,000 reviews)
"Great place to stay"
United States
Harry
The price is RM382
RM428 total
includes taxes & fees
7 Jul - 8 Jul
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (386 reviews)
"Love this awesome place best around "
United States
Christopher
The price is RM474
RM531 total
includes taxes & fees
9 Jul - 10 Jul
SpringHill Suites by Marriott Edgewood/Aberdeen
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (348 reviews)
"Would definitely stay here again"
United States
Marie
The price is RM447
RM500 total
includes taxes & fees
5 Jul - 6 Jul
Fairfield Inn & Suites by Marriott Aberdeen
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
2.0 star property
Havre De Grace
6.6 out of 10, (1,001 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
The price is RM210
RM235 total
includes taxes & fees
6 Jul - 7 Jul
Super 8 by Wyndham Havre De Grace Aberdeen Area
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is RM927
RM1,057 total
includes taxes & fees
5 Jul - 6 Jul
Flag House Inn
In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (928 reviews)
"Room was clean and staff took very good care of us"
United States
Carol
The price is RM408
RM453 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Grasonville near Kent Island
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (150 reviews)
"It was such a lovely quaint resort. I loved everything about staying there. Thank you."
United States
Sue
The price is RM666
RM878 total
includes taxes & fees
16 Jul - 17 Jul
Kent Island Resort
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (696 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
The price is RM430
RM477 total
includes taxes & fees
12 Jul - 13 Jul
Holiday Inn Express & Suites Middletown by IHG
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,867 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is RM368
RM559 total
includes taxes & fees
12 Jul - 13 Jul
Historic Inns of Annapolis
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (558 reviews)
"The staff was wonderful! the place was nice and clean. everything was in walking distance. highly recommend staying here if visiting."
United States
Danielle
The price is RM590
RM660 total
includes taxes & fees
6 Jul - 7 Jul
Vandiver Inn
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,001 reviews)
"Convenient location, clean room and delicious breakfast"
United States
Connie
The price is RM367
RM411 total
includes taxes & fees
9 Jul - 10 Jul
Hampton Inn & Suites Edgewood/Aberdeen-South
Lake

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is RM727
RM807 total
includes taxes & fees
8 Jul - 9 Jul
Inn at Huntingfield Creek
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (408 reviews)
"Great place to stay"
United States
Angelique
The price is RM486
RM539 total
includes taxes & fees
2 Aug - 3 Aug
Fairfield Inn & Suites by Marriott Middletown
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

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

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Staff was friendly, helpful and wonderful. Room was good, location is great."
LAURA 3-night trip
Posted 1 hour ago
Historic Inns of Annapolis

More cheap stays in Chestertown

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

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

2112a Emmorton Park Road Edgewood MD
The price is RM255 per night from 6 Jul to 7 Jul
RM255
RM286 total
6 Jul - 7 Jul
includes taxes & fees
7.4/10 Good! (1,155 reviews)

Frequently asked questions

Where is the best place for a stay in Chestertown?
Based on our traveller data, Comfort Inn & Suites Chestertown is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good options for your trip include Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing. 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 free WiFi, 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, free WiFi and free self-parking. 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 44 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 23Ā°C, while the coldest months are January and February, with an average of 4Ā°C. Average annual precipitation for Chestertown is 1232 mm.

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