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Chestertown Hotels

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Top 10 trending Chestertown hotels

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 €105
includes taxes & fees
17 Aug - 18 Aug
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 €69
includes taxes & fees
13 Aug - 14 Aug
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (58)
"Great place to get some quiet rest by the water"
The price is €127
includes taxes & fees
5 Aug - 6 Aug
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 €61
includes taxes & fees
5 Aug - 6 Aug
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 €133
includes taxes & fees
10 Aug - 11 Aug
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, (1007)
"I loved my stay"
The price is €77
includes taxes & fees
10 Aug - 11 Aug
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 €152
includes taxes & fees
13 Aug - 14 Aug
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 €57
includes taxes & fees
2 Sept - 3 Sept
Quality Inn & Suites Bel Air I-95 Exit 77A

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 €54
includes taxes & fees
11 Aug - 12 Aug
Super 8 by Wyndham Aberdeen MD

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (975)
"Great spot with beautiful views. "
The price is €148
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Kent Island Marina

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.4 out of 10, Good, (1003)
"It was a very nice stay. I enjoyed the peaceful atmosphere. Thank you. "
The price is €97
includes taxes & fees
1 Sept - 2 Sept
Country Inn & Suites by Radisson, Baltimore North, 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 €86
includes taxes & fees
2 Sept - 3 Sept
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 €108
includes taxes & fees
31 Aug - 1 Sept
Best Western Plus Hotel & Conference Center

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1822)
"Loved the hotel-great location "
Historic Inns of Annapolis

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (850)
"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 €225
includes taxes & fees
14 Aug - 15 Aug
Annapolis Waterfront Hotel, Autograph Collection

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1008)
"Great location friendly staff "
The price is €97
includes taxes & fees
31 Aug - 1 Sept
Fairfield Inn & Suites by Marriott White Marsh

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (953)
"The staff was great."
The price is €49
includes taxes & fees
11 Aug - 12 Aug
Americas Best Value Inn Edgewood

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (738)
"clean, nice staff, nice breakfast"
The price is €90
includes taxes & fees
6 Aug - 7 Aug
Comfort Inn & Suites Aberdeen near APG

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (107)
"Hotel was great and peaceful. This hotel was water front. Nice surroundings!! I enjoyed to stay here."
The price is €178
includes taxes & fees
3 Sept - 4 Sept
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is €218
includes taxes & fees
24 Aug - 25 Aug
The Inn at Chesapeake Bay Beach Club
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Learn more about Chestertown

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

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Best guest reviews of Chestertown

Top Chestertown Hotel Reviews

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 The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown as top options for your stay. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Chestertown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all 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 accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers 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 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's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels 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's the best hotel in Chestertown to learn about 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 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.

What is the best spa hotel in Chestertown?

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