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Hotels with Pool & Resorts in Chestertown from AU$147

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Check availability on Chestertown Hotels with Pool

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, (1006)
"Great stay at a great price "
The price is AU$152
includes taxes & fees
21 Aug - 22 Aug
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (912)
"We had a great stay!"
The price is AU$174
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express White Marsh by IHG
Best Western Kent Narrows Inn
Indoor pool

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1003)
"Excellent location"
The price is AU$186
includes taxes & fees
24 Aug - 25 Aug
Best Western Kent Narrows Inn
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
8.2 out of 10, Very good, (61)
"Great place to get some quiet rest by the water"
The price is AU$226
includes taxes & fees
19 Aug - 20 Aug
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, (794)
"It was a clean comfortable spot to rest for the night. "
The price is AU$194
includes taxes & fees
24 Aug - 25 Aug
Comfort Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (96)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is AU$247
includes taxes & fees
28 Aug - 29 Aug
First Floor Studio Apartment in Historic Chestertown
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (603)
"Very beautiful and clean properly with great staff. "
The price is AU$198
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express & Suites Middletown by IHG
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is AU$402
includes taxes & fees
17 Aug - 18 Aug
Inn at Haven Harbour
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, (887)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is AU$223
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn
Free daily self-service breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Wonerful place, all good..Hotel,area, staff."
The price is AU$147
includes taxes & fees
15 Sept - 16 Sept
Quality Inn
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"It was a beautiful hotel - super fun sitting area/lobby. Very quiet and peaceful experience. "
Joseph 6-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh

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: Provides 3 bars, a seasonal outdoor pool and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool and free self parking. Hampton Inn Baltimore/Glen Burnie: Offers complimentary high-speed (wired) Internet access, 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.