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Find hotels in Chestertown, MD from ₩79,210

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Compare 1,075 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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 ₩289,763
₩352,353 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩89,933
₩100,725 total
includes taxes & fees
Aug 26 - Aug 27
Motel Edgewood

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (388)
"Good location."
The price is ₩105,831
₩117,472 total
includes taxes & fees
Sep 1 - Sep 2
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 ₩123,277
₩137,134 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩183,047
₩203,182 total
includes taxes & fees
Aug 26 - Aug 27
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (802)
"staff was friendly, accomodations were fine."
The price is ₩151,710
₩168,398 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Chestertown

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is ₩260,113
₩654,392 total
includes taxes & fees
Sep 8 - Sep 9
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 ₩142,509
₩158,185 total
includes taxes & fees
Sep 4 - Sep 5
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 ₩408,018
₩465,140 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩227,494
₩303,125 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩121,727
₩135,117 total
includes taxes & fees
Sep 24 - Sep 25
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. "
The price is ₩294,956
₩336,250 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩536,829
₩687,682 total
includes taxes & fees
Sep 11 - Sep 12
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 ₩214,801
₩238,433 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩193,009
₩220,030 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩186,783
₩207,329 total
includes taxes & fees
Sep 1 - Sep 2
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 ₩197,990
₩260,170 total
includes taxes & fees
Sep 1 - Sep 2
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 ₩175,230
₩196,258 total
includes taxes & fees
Aug 31 - Sep 1
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 ₩90,901
₩101,809 total
includes taxes & fees
Aug 26 - Aug 27
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 ₩148,043
₩164,328 total
includes taxes & fees
Sep 7 - Sep 8
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.
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Stay near popular Chestertown attractions

Wilmer Park

Wilmer Park

Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.

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 harbor.

Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favorite 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 trip. 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, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your scheduled arrival. If your reservation is non-refundable, 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.

Where can I learn more about changing or cancelling my trip to Chestertown?

For more details about rescheduling or cancelling your trip to Chestertown, click here.

What's the best hotel for families 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 kid-friendly vacation. Kids of all ages will also enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best LGBTQ-friendly accommodation 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 other good options for your trip. See all available hotels listed as LGBTQ-friendly in Chestertown.

What's the best pet-friendly hotel in Chestertown?

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

Where is the best hotel to stay near Washington College?

Adjacent to Washington College, Driftwood Inn is one of the top choices for your stay based on our traveler data, and this property offers free parking and free WiFi. Other good options close by include Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.

What about the best place to stay near Rolphs Wharf Marina?

One of the top choices for your stay is Comfort Inn & Suites Chestertown, located 4.1 mi (6.6 km) from Rolphs Wharf Marina, and this hotel offers free breakfast and free parking. Driftwood Inn and Red Roof Inn & Suites Chestertown are two other good options within a few miles.

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 accommodations with pools in Chestertown?

The Lodge at Great Oak Landing is a top lodge with a seasonal outdoor pool, 3 bars, and free WiFi. View all hotels with pools in Chestertown.

What's the best hotel for staying near Salisbury - Ocean City Wicomico Regional Airport (SBY)?

Country Inn & Suites by Radisson, Salisbury, MD is one of the top choices for your stay and is a popular 3-star hotel featuring free breakfast and an indoor pool. It's located 2.2 mi (3.6 km) from Salisbury - Ocean City Wicomico Regional Airport. Other options close to the airport include Microtel Inn & Suites by Wyndham Salisbury and Sleep Inn Salisbury.

How is it to stay in Chestertown?

Visitors to Chestertown are sure to enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals, and art. In Chestertown, there are 44 hotels and other accommodations to choose from. Find out more about Chestertown.

What are the top places to visit 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 agenda are Rolphs Wharf Marina and Chestertown Historic District. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.