Chestertown Hotels with Swimming Pool

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 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, (861)
"Everything was well!"
United States
Ahmed
The price is RM404
RM449 total
includes taxes & fees
25 Jan - 26 Jan 2026
Comfort Inn & Suites Chestertown
1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is RM401
RM458 total
includes taxes & fees
31 Dec - 1 Jan 2026
The Lodge at Great Oak Landing
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, (325)
"Clean room, great staff, recommended. "
United States
Tom
The price is RM437
RM486 total
includes taxes & fees
5 Jan - 6 Jan 2026
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, (942)
"It was very comfortable and clean"
United States
Maria
The price is RM320
RM355 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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 RM275
RM306 total
includes taxes & fees
27 Jan - 28 Jan 2026
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, (868)
"Amazing stay"
United States
Katiana
The price is RM385
RM428 total
includes taxes & fees
13 Jan - 14 Jan 2026
Hampton Inn Middletown
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, (634)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
The price is RM390
RM437 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hilton Garden Inn Aberdeen
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 RM518
RM717 total
includes taxes & fees
1 Jan - 2 Jan 2026
Kent Island Resort
Indoor pool, pool loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (683)
"friendly staff, clean room / lobby, nice bar, everything was great"
United States
William
The price is RM470
RM522 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Staff was extremely courteous and helpful. Breakfast was great. The room was very clean. The pool was well maintained. It was a great hotel all around."
Richard 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South

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. Provides 2 bars, a seasonal outdoor pool and spa services. Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Best Western Plus Hotel & Conference Center: 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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