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Hotels with Pool & Resorts in Chestertown from NZ$164

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Check availability on Chestertown Hotels with Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Best Chestertown Hotels with Pool

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 NZ$164
includes taxes & fees
12 Oct - 13 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, (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
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 NZ$212
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express White Marsh by IHG
The Lodge at Great Oak Landing
Room, 1 King Bed with Sofa bed, Marina View

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
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (102)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is NZ$272
includes taxes & fees
7 Oct - 8 Oct
First Floor Studio Apartment in Historic Chestertown
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 NZ$218
includes taxes & fees
3 Nov - 4 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 NZ$192
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, (625)
"Check in staff was awesome!"
The price is NZ$227
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 NZ$274
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

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

10/10 Excellent
"Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!"
Christine 2-night trip
Posted 1 day ago
Sagamore Pendry Baltimore

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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.