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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Top Chestertown Hotels with a Pool

The Lodge at Great Oak Landing
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (68)
"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 ₩182,111
₩202,144 total
includes taxes & fees
Sep 21 - Sep 22
The Lodge at Great Oak Landing
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (897)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is ₩185,828
₩206,270 total
includes taxes & fees
Oct 19 - Oct 20
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Belcamp - Aberdeen Area by IHG
Indoor pool

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.4 out of 10, Very Good, (719)
"It was a good location. Workers are super friendly and attentive. "
The price is ₩121,132
₩135,668 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Belcamp - Aberdeen Area by IHG
Quality Inn
Lobby

Quality Inn

2.5 star property
7.8 out of 10, Good, (828)
"Great place and great staff"
The price is ₩146,253
₩162,340 total
includes taxes & fees
Sep 21 - Sep 22
Quality Inn
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, (817)
"Friendly staff, clean room, convenient location. "
The price is ₩159,715
₩177,284 total
includes taxes & fees
Sep 28 - Sep 29
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, (281)
"Friendly staff, comfortable bed and clean room "
The price is ₩143,156
₩158,903 total
includes taxes & fees
Sep 28 - Sep 29
Fairfield Inn & Suites by Marriott Middletown
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1003)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is ₩121,683
₩136,285 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn & Suites Edgewood/Aberdeen-South
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 ₩213,702
₩237,213 total
includes taxes & fees
Sep 21 - Sep 22
Mariners Motel
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Seasonal outdoor pool

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1008)
"I love how easy it was to check in My key ready friendly staff Breakfast was wonderful helpful peipke"
The price is ₩121,683
₩136,285 total
includes taxes & fees
Sep 28 - Sep 29
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
"Fine would stay again"
DAVID 1-night trip
Posted 2 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

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: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Features buffet, an indoor pool, and free self parking. Sagamore Pendry Baltimore: Offers complimentary 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 like 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 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.