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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
Nov 6 - Nov 7
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Nov 7 - Nov 8
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top Chestertown Hotels with a Pool

Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
8.0 out of 10, Very Good, (74)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Nov 9 - Nov 10
Total with taxes and fees
The Lodge at Great Oak Landing
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (838)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
$102 nightly
The price is $113
Nov 9 - Nov 10
Total with taxes and fees
Comfort Inn & Suites Chestertown
Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
$144 nightly
The price is $159
Nov 10 - Nov 11
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Indoor pool
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (300)
"Friendly staff, comfortable bed and clean room "
United States
DAVID
$108 nightly
The price is $120
Nov 16 - Nov 17
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1000)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
$82 nightly
The price is $91
Nov 18 - Nov 19
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (914)
"Excellent, pet friendly, clean, convenient, and beautiful "
United States
John
$95 nightly
The price is $105
Dec 1 - Dec 2
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Free daily self-serve breakfast
Quality Inn
Quality Inn
2.5 star property
7.6 out of 10, Good, (1001)
"Good property "
United States
Deryahna
$68 nightly
The price is $75
Dec 8 - Dec 9
Total with taxes and fees
Quality Inn
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
$90 nightly
The price is $101
Nov 25 - Nov 26
Total with taxes and fees
Hampton Inn & Suites Baltimore/Aberdeen
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
8.0 out of 10, Very Good, (1000)
"The experience was as expected. Everything worked well and the staff were very friendly. I would recommend this hotel for a short stay."
United States
Bernadette
$92 nightly
The price is $102
Nov 16 - Nov 17
Total with taxes and fees
Best Western Kent Narrows Inn
Exterior
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (425)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
$207 nightly
The price is $230
Dec 1 - Dec 2
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Great breakfast, good location, clean."
william 3-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh

Frequently asked questions

What are some accommodations 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: Offers complimentary wired internet access, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Features buffet, an indoor pool, and free self parking. Hilton Garden Inn Baltimore/White Marsh: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services.
What is there to see and do in Chestertown?
Surround yourself with nature at Chesapeake Bay and Chestertown Dog Park. 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 offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.

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