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Top hotels and accommodation in Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
The price is NZ$218
includes taxes & fees
3 Nov - 4 Nov
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (399)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is NZ$154
includes taxes & fees
12 Oct - 13 Oct
Red Roof Inn & Suites Chestertown

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (70)
"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 NZ$259
includes taxes & fees
7 Oct - 8 Oct
The Lodge at Great Oak Landing

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
The price is NZ$121
includes taxes & fees
27 Oct - 28 Oct
Driftwood Inn

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

3.0 star property
7.0 out of 10, Good, (1003)
"Had a nice stay "
The price is NZ$152
includes taxes & fees
8 Oct - 9 Oct
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is NZ$242
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG

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

2.5 star property
7.2 out of 10, Good, (1002)
"Fine would stay again"
The price is NZ$119
includes taxes & fees
2 Nov - 3 Nov
Quality Inn & Suites Bel Air I-95 Exit 77A

Best Western Plus Hotel & Conference Center

2.5 star property
7.8 out of 10, Good, (1005)
"Great stay"
The price is NZ$215
includes taxes & fees
2 Nov - 3 Nov
Best Western Plus Hotel & Conference Center

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
7.2 out of 10, Good, (1001)
"I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10...
The price is NZ$193
includes taxes & fees
14 Oct - 15 Oct
Country Inn & Suites by Radisson, Baltimore North, MD

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (633)
"Great location and rooms. Great place!"
The price is NZ$284
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Kent Narrows & Marina

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1002)
"Great location friendly staff "
The price is NZ$192
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott White Marsh

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (774)
"Room was clean, price is very reasonable. "
The price is NZ$178
includes taxes & fees
3 Nov - 4 Nov
Comfort Inn & Suites Aberdeen near APG

Super 8 by Wyndham Aberdeen MD

2.0 star property
7.0 out of 10, Good, (849)
"Parking was easy. Bed was super comfy. "
The price is NZ$116
includes taxes & fees
13 Oct - 14 Oct
Super 8 by Wyndham Aberdeen MD

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1002)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is NZ$164
includes taxes & fees
12 Oct - 13 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn Baltimore Bayview Campus

3.5 star property
9.0 out of 10, Wonderful, (1001)
"We’ve stayed here two times already and always enjoyed it! Clean rooms, friendly staff, free parking and many shopping options close by!"
The price is NZ$263
includes taxes & fees
15 Oct - 16 Oct
Hampton Inn Baltimore Bayview Campus

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Hotel was great, beautiful location near the water"
The price is NZ$279
includes taxes & fees
16 Oct - 17 Oct
Hilton Garden Inn Kent Island Marina

Americas Best Value Inn Edgewood

2.0 star property
5.6 out of 10, (988)
"I always have a good experience with the staff. The motel might not be the greatest, but the staff is always friendly and accommodating. That's why I keep coming back."
The price is NZ$109
includes taxes & fees
19 Oct - 20 Oct
Americas Best Value Inn Edgewood

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is NZ$424
includes taxes & fees
21 Oct - 22 Oct
Kent Island Resort

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (581)
"This Hotel was excellent in all ways. "
The price is NZ$187
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Baltimore/Aberdeen

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1835)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
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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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 harbour.

Photo by Assya A
Open Photo by Assya A

Top Chestertown Hotel Reviews

More cheap accommodation in Chestertown

More cheap accommodation in Chestertown

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chestertown offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 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 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 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.

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 41 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.

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