Photo by Patricia Knorr

Chestertown Hotels from S$82

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chestertown hotels

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is S$323
includes taxes & fees
8 Sept - 9 Sept
Inn at Haven Harbour

Motel Edgewood

2.0 star property
8.6 out of 10, Excellent, (7)
"Bed was clean and crisply made. Occupants were respectful of sleeping hours. Check-in and check-out were simple. Parking was convenient and had easy access to the highway."
The price is S$84
includes taxes & fees
8 Sept - 9 Sept
Motel Edgewood

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (388)
"Good location."
The price is S$109
includes taxes & fees
1 Sept - 2 Sept
Red Roof Inn & Suites Chestertown

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (87)
"Owner was very nice. "
The price is S$127
includes taxes & fees
26 Aug - 27 Aug
Relax Inn Smyrna

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (66)
"Great place to get some quiet rest by the water"
The price is S$188
includes taxes & fees
26 Aug - 27 Aug
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (803)
"staff was friendly, accomodations were fine."
The price is S$156
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is S$606
includes taxes & fees
26 Aug - 27 Aug
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (265)
"I’ve stayed here a few times now and everyone is so pleasant and helpful. "
The price is S$146
includes taxes & fees
4 Sept - 5 Sept
Fairfield Inn & Suites by Marriott Middletown

86 State Circle - Luxury Boutique Hotel

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$358
includes taxes & fees
26 Aug - 27 Aug
86 State Circle - Luxury Boutique Hotel

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (111)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is S$281
includes taxes & fees
26 Aug - 27 Aug
Kent Island Resort

Quality Inn

2.5 star property
7.6 out of 10, Good, (1001)
"Wonerful place, all good..Hotel,area, staff."
The price is S$125
includes taxes & fees
24 Sept - 25 Sept
Quality Inn

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"Great boutique hotel for an overnight. Terrific location and accommodating staff. Couldn't have been a better stay. "
134 Prince - Luxury Boutique Hotel

Sagamore Pendry Baltimore

5.0 star property
9.4 out of 10, Exceptional, (1002)
"A fantastic hotel. Great location, pool, services, food, and rooms. One of our best hotel stays in years."
The price is S$595
includes taxes & fees
7 Sept - 8 Sept
Sagamore Pendry Baltimore

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is S$221
includes taxes & fees
26 Aug - 27 Aug
Mariners Motel

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (76)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is S$204
includes taxes & fees
26 Aug - 27 Aug
Flag House Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (893)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is S$192
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

The Inn at Henderson's Wharf, Ascend Hotel Collection

3.0 star property
9.2 out of 10, Wonderful, (714)
"Second time staying here - absolutely lovely. "
The price is S$241
includes taxes & fees
1 Sept - 2 Sept
The Inn at Henderson's Wharf, Ascend Hotel Collection

Hilton Garden Inn Bel Air

3.0 star property
9.4 out of 10, Exceptional, (209)
"Very quick and easy check in "
The price is S$182
includes taxes & fees
31 Aug - 1 Sept
Hilton Garden Inn Bel Air

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (884)
"Great price, nice staff. "
The price is S$94
includes taxes & fees
26 Aug - 27 Aug
Days Inn by Wyndham Aberdeen

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (608)
"Very beautiful and clean properly with great staff. "
The price is S$152
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express & Suites Middletown by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

More cheap stays in Chestertown

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Red Roof Inn & Suites Chestertown and Driftwood Inn 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 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. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Chestertown Historic District. 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.