Hotels with Swimming Pools in Chestertown

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Our top choices for Chestertown hotels with a pool

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (864)
"Everything was well!"
United States
Ahmed
The price is S$143
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (331)
"Clean room, great staff, recommended. "
United States
Tom
The price is S$154
includes taxes & fees
11 Jan - 12 Jan
Fairfield Inn & Suites by Marriott Middletown

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (947)
"It was very comfortable and clean"
United States
Maria
The price is S$124
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is S$113
includes taxes & fees
30 Jan - 31 Jan
Hilton Garden Inn Aberdeen

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Great stay"
United States
Edward
The price is S$97
includes taxes & fees
5 Feb - 6 Feb
Quality Inn Smyrna

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870)
"Amazing stay"
United States
Katiana
The price is S$135
includes taxes & fees
13 Jan - 14 Jan
Hampton Inn Middletown

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is S$225
includes taxes & fees
11 Jan - 12 Jan
Kent Island Resort

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is S$254
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1005)
"Room was great and staff excellent. "
United States
Robert
The price is S$123
includes taxes & fees
9 Jan - 10 Jan
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.

Top Chestertown Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool and free self parking. Red Roof Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Offers complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. Hilton Garden Inn Baltimore/White Marsh: Offers a health club, an indoor pool and a snack bar/deli.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Historical Society of Kent County Maryland, Chestertown Historic District and Rolphs Wharf Marina during your stay.
When is the best time to book a hotel with a pool in Chestertown?
You may want to consider a place to stay that has an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.

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