Hotels with Pool & Resorts in Chestertown from NZ$131

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Check availability on Chestertown Hotels with Pool

Tonight
4 Jan - 5 Jan
Tomorrow
5 Jan - 6 Jan
Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan

Our top choices for Chestertown hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (863)
"Everything was well!"
United States
Ahmed
The price is NZ$183
includes taxes & fees
26 Jan - 27 Jan
Comfort Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is NZ$275
includes taxes & fees
6 Jan - 7 Jan
First Floor Studio Apartment in Historic Chestertown
Indoor pool
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (330)
"Clean room, great staff, recommended. "
United States
Tom
The price is NZ$208
includes taxes & fees
11 Jan - 12 Jan
Fairfield Inn & Suites by Marriott Middletown
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

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 NZ$167
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Hilton Garden Inn Aberdeen

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 NZ$152
includes taxes & fees
15 Jan - 16 Jan
Hilton Garden Inn Aberdeen
Free daily self-service breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1002)
"Great stay"
United States
Edward
The price is NZ$131
includes taxes & fees
3 Feb - 4 Feb
Quality Inn Smyrna
Indoor pool
Hampton Inn Middletown

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 NZ$183
includes taxes & fees
13 Jan - 14 Jan
Hampton Inn Middletown
Aerial view
Kent Island Resort

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 NZ$307
includes taxes & fees
6 Jan - 7 Jan
Kent Island Resort
Exterior
The Inn at Chesapeake Bay Beach Club

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)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is NZ$344
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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 NZ$167
includes taxes & fees
10 Jan - 11 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.
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Top Chestertown Hotel Reviews

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

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

10/10 Excellent
"Decent place not loud quiet and out of the way."
Tarrell 1-night trip
Posted 7 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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.