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Hotels with Swimming Pools in Chestertown

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
10 Oct - 12 Oct
Next weekend
17 Oct - 19 Oct

Top Hotels with Swimming Pools in Chestertown

Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool

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 S$123
includes taxes & fees
16 Oct - 17 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (904)
"Nice Holiday Inn Express with great water views."
The price is S$176
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express White Marsh by IHG
Indoor pool

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (943)
"Staff was very nice and rooms were clean. Breakfast was great too!!"
The price is S$160
includes taxes & fees
29 Oct - 30 Oct
Holiday Inn Express White Marsh by IHG
The Lodge at Great Oak Landing
1 bedroom, free WiFi, bed sheets

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 S$195
includes taxes & fees
8 Oct - 9 Oct
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
The price is S$165
includes taxes & fees
2 Nov - 3 Nov
Comfort Inn & Suites Chestertown
Fairfield Inn & Suites by Marriott Middletown
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (289)
"Friendly staff, comfortable bed and clean room "
The price is S$144
includes taxes & fees
19 Oct - 20 Oct
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG
Indoor pool

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (626)
"Check in staff was awesome!"
The price is S$170
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express & Suites Middletown by IHG
Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is S$206
includes taxes & fees
2 Nov - 3 Nov
Mariners Motel
Inn at Huntingfield Creek
Outdoor pool, pool loungers

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
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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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Easy access, dmooth check in, felt safe parking, close to port. "
Roberta 1-night trip
Posted 5 days ago
Best Western Plus Hotel & Conference Center

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Red Roof Inn & Suites Chestertown: Offers full, a seasonal outdoor pool and free self parking. Comfort Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool and free self parking.
What is there to see and do in Chestertown?
Make a point to visit attractions such as Chestertown Dog Park and Crumpton Auction. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater 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.