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Find hotels in Chestertown, MD from NT$1,691

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Compare 1,073 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (809)
"Friendly staff, clean room, convenient location. "
The price is NT$3,368
NT$3,738 total
includes taxes & fees
Sep 14 - Sep 15
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (391)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is NT$2,343
NT$2,601 total
includes taxes & fees
Sep 10 - Sep 11
Red Roof Inn & Suites Chestertown

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 NT$4,052
NT$4,498 total
includes taxes & fees
Sep 14 - Sep 15
The Lodge at Great Oak Landing

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is NT$4,013
NT$4,454 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Express Annapolis East-Kent Island by IHG

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
7.0 out of 10, Good, (1016)
"I loved my stay"
The price is NT$2,350
NT$2,714 total
includes taxes & fees
Sep 4 - Sep 5
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (620)
"Great location"
The price is NT$4,870
NT$5,406 total
includes taxes & fees
Sep 14 - Sep 15
Hyatt Place Kent Narrows & Marina

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1000)
"Great service always "
The price is NT$2,938
NT$3,394 total
includes taxes & fees
Sep 4 - Sep 5
Country Inn & Suites by Radisson, Baltimore North, MD

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

2.5 star property
7.2 out of 10, Good, (1020)
"It's very clean, safe with easy parking, and very easy to get to it "
The price is NT$1,691
NT$1,894 total
includes taxes & fees
Oct 1 - Oct 2
Quality Inn & Suites Bel Air I-95 Exit 77A

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1011)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is NT$2,708
NT$3,033 total
includes taxes & fees
Sep 9 - Sep 10
Hampton Inn & Suites Edgewood/Aberdeen-South

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (837)
"Staff is great & rooms always good "
The price is NT$1,719
NT$1,925 total
includes taxes & fees
Sep 16 - Sep 17
Super 8 by Wyndham Aberdeen MD

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1001)
"Nice hotel "
The price is NT$3,280
NT$3,854 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Plus Hotel & Conference Center

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (993)
"Hotel was great, beautiful location near the water"
The price is NT$4,568
NT$5,071 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Garden Inn Kent Island Marina

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 NT$6,054
NT$7,883 total
includes taxes & fees
Sep 21 - Sep 22
Kent Island Resort

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1001)
"Great location friendly staff "
The price is NT$3,098
NT$3,579 total
includes taxes & fees
Sep 10 - Sep 11
Fairfield Inn & Suites by Marriott White Marsh

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1851)
"Excellent location, clean, friendly staff"
Historic Inns of Annapolis

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (962)
"The staff was great."
The price is NT$1,410
NT$1,579 total
includes taxes & fees
Sep 18 - Sep 19
Americas Best Value Inn Edgewood

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (563)
"Great stay!"
The price is NT$3,350
NT$3,752 total
includes taxes & fees
Oct 2 - Oct 3
Hampton Inn & Suites Baltimore/Aberdeen

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (860)
"Easy check in, clean and close to everything "
The price is NT$7,284
NT$8,304 total
includes taxes & fees
Sep 28 - Sep 29
Annapolis Waterfront Hotel, Autograph Collection

Hampton Inn Baltimore Bayview Campus

3.5 star property
9.0 out of 10, Wonderful, (1000)
"The location is good for our needs"
The price is NT$3,994
NT$4,693 total
includes taxes & fees
Sep 18 - Sep 19
Hampton Inn Baltimore Bayview Campus

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1012)
"I love how easy it was to check in My key ready friendly staff Breakfast was wonderful helpful peipke"
The price is NT$2,655
NT$2,974 total
includes taxes & fees
Sep 9 - Sep 10
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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

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

More cheap stays in Chestertown

More cheap stays in Chestertown

Hotels in Chestertown with star-rating

Hotels in Chestertown with star-rating

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 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.