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Find hotels in Chestertown, MD from ₩77,085

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Compare 1,077 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Our top choices for Chestertown hotels

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (897)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ₩185,828
₩206,270 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Annapolis East-Kent Island by IHG

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
The price is ₩209,366
₩234,490 total
includes taxes & fees
Sep 21 - Sep 22
Vandiver Inn

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"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 ₩213,702
₩237,213 total
includes taxes & fees
Sep 21 - Sep 22
Mariners Motel

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is ₩182,111
₩202,144 total
includes taxes & fees
Sep 21 - Sep 22
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (817)
"Friendly staff, clean room, convenient location. "
The price is ₩159,715
₩177,284 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (395)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ₩105,290
₩116,871 total
includes taxes & fees
Sep 24 - Sep 25
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is ₩87,408
₩97,030 total
includes taxes & fees
Oct 14 - Oct 15
Driftwood Inn

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (736)
"Great stay. "
The price is ₩168,690
₩194,830 total
includes taxes & fees
Sep 21 - Sep 22
SpringHill Suites Baltimore White Marsh/Middle River

Relax Inn Smyrna

2.0 star property
7.8 out of 10, Good, (88)
"Owner was very nice. "
The price is ₩122,647
₩136,432 total
includes taxes & fees
Sep 21 - Sep 22
Relax Inn Smyrna

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (281)
"Friendly staff, comfortable bed and clean room "
The price is ₩143,156
₩158,903 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
9.0 out of 10, Wonderful, (518)
"Clean hotel, good hot breakfast, comfortable bed."
The price is ₩119,756
₩134,126 total
includes taxes & fees
Sep 21 - Sep 22
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Quality Inn

2.5 star property
7.6 out of 10, Good, (1003)
"Wonerful place, all good..Hotel,area, staff."
The price is ₩122,646
₩136,136 total
includes taxes & fees
Sep 24 - Sep 25
Quality Inn

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (833)
"Decent for a Hampton Inn"
The price is ₩150,933
₩167,536 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn Middletown

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
The price is ₩220,612
₩244,880 total
includes taxes & fees
Sep 29 - Sep 30
Inn at Huntingfield Creek

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (619)
"Check in staff was awesome!"
The price is ₩147,286
₩163,487 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Express & Suites Middletown by IHG

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 ₩256,070
₩314,791 total
includes taxes & fees
Sep 25 - Sep 26
Inn at Haven Harbour

Quality Inn

2.5 star property
7.8 out of 10, Good, (828)
"Great place and great staff"
The price is ₩146,253
₩162,340 total
includes taxes & fees
Sep 21 - Sep 22
Quality Inn

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1003)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is ₩121,683
₩136,285 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn & Suites Edgewood/Aberdeen-South

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (24)
"Very friendly staff!"
The price is ₩293,447
₩334,530 total
includes taxes & fees
Sep 21 - Sep 22
134 Prince - Luxury Boutique Hotel

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is ₩234,143
₩310,559 total
includes taxes & fees
Oct 1 - Oct 2
Kent Island Resort
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

Quaint Chestertown awaits: its sports, university life, festivals, and more!

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

More cheap stays in Chestertown

More cheap stays in Chestertown

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 The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown 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 42 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.