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Find hotels in Chestertown, MD from ₩73,225

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Compare 1,078 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, (791)
"It was a clean comfortable spot to rest for the night. "
The price is ₩152,355
₩169,114 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (384)
"Good location."
The price is ₩100,042
₩111,048 total
includes taxes & fees
Aug 10 - Aug 11
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (57)
"Great place to get some quiet rest by the water"
The price is ₩183,827
₩204,047 total
includes taxes & fees
Aug 5 - Aug 6
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is ₩88,231
₩97,943 total
includes taxes & fees
Aug 5 - Aug 6
Driftwood Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
The price is ₩198,694
₩220,550 total
includes taxes & fees
Aug 17 - Aug 18
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, (1005)
"I loved my stay"
The price is ₩107,823
₩124,535 total
includes taxes & fees
Aug 10 - Aug 11
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, (603)
"Great place to stay. "
The price is ₩220,926
₩245,228 total
includes taxes & fees
Aug 11 - Aug 12
Hyatt Place Kent Narrows & Marina

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

2.5 star property
7.2 out of 10, Good, (1007)
"I liked everything about the hotel was very clean friendly staff "
The price is ₩81,562
₩91,348 total
includes taxes & fees
Aug 31 - Sep 1
Quality Inn & Suites Bel Air I-95 Exit 77A

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (975)
"Friendly staff, nice environment"
The price is ₩223,274
₩247,834 total
includes taxes & fees
Aug 19 - Aug 20
Hilton Garden Inn Kent Island Marina

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1002)
"It was a very nice stay. I enjoyed the peaceful atmosphere. Thank you. "
The price is ₩134,987
₩155,909 total
includes taxes & fees
Sep 1 - Sep 2
Country Inn & Suites by Radisson, Baltimore North, MD

Super 8 by Wyndham Aberdeen MD

2.0 star property
6.8 out of 10, (827)
"Everything is good for a business trip, simply sleep"
The price is ₩79,130
₩88,626 total
includes taxes & fees
Sep 1 - Sep 2
Super 8 by Wyndham Aberdeen MD

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Great stay at a great price "
The price is ₩126,539
₩141,723 total
includes taxes & fees
Sep 2 - Sep 3
Hampton Inn & Suites Edgewood/Aberdeen-South

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1003)
"Convenient location"
The price is ₩148,382
₩174,349 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Plus Hotel & Conference Center

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (953)
"The staff was great."
The price is ₩70,863
₩79,367 total
includes taxes & fees
Aug 10 - Aug 11
Americas Best Value Inn Edgewood

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1819)
"Loved the hotel-great location "
The price is ₩141,610
₩208,955 total
includes taxes & fees
Aug 10 - Aug 11
Historic Inns of Annapolis

Super 8 by Wyndham Havre De Grace Aberdeen Area

2.0 star property
6.6 out of 10, (936)
"It was nice "
The price is ₩73,225
₩82,013 total
includes taxes & fees
Aug 5 - Aug 6
Super 8 by Wyndham Havre De Grace Aberdeen Area

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (736)
"clean, nice staff, nice breakfast"
The price is ₩128,734
₩144,182 total
includes taxes & fees
Aug 6 - Aug 7
Comfort Inn & Suites Aberdeen near APG

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (849)
"We were pleased with the staff, room and the view. We were disappointed that there was no restaurant or bar on the property as the description led us to believe."
The price is ₩305,892
₩348,716 total
includes taxes & fees
Aug 10 - Aug 11
Annapolis Waterfront Hotel, Autograph Collection

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1007)
"Great location friendly staff "
The price is ₩134,640
₩155,510 total
includes taxes & fees
Aug 31 - Sep 1
Fairfield Inn & Suites by Marriott White Marsh

Days Inn by Wyndham Aberdeen

2.0 star property
7.0 out of 10, Good, (874)
"Great price, nice staff. "
The price is ₩93,789
₩105,044 total
includes taxes & fees
Aug 11 - Aug 12
Days Inn by Wyndham Aberdeen
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, art, 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

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 place to stay on a budget in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travelers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

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 accommodation for a romantic vacation to Chestertown?

Red Roof Inn & Suites Chestertown is a favorite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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's the best place to stay in Chestertown to absorb the local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also notable landmarks to visit include Historical Society of Kent County Maryland. See more options for historical stays 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 is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness center. See all spa hotels 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.