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Hotels with Pool & Resorts in Chestertown from AU$144

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Check availability on Chestertown Hotels with Pool

Best Chestertown Hotels with Pool

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, (831)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
United States
Charlie
The price is AU$174
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn & Suites Chestertown
Room, 1 King Bed with Sofa bed, Marina View
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
7.8 out of 10, Good, (70)
"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!!"
United States
Melissa
The price is AU$233
includes taxes & fees
20 Oct - 21 Oct
The Lodge at Great Oak Landing
Property grounds
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (103)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
United States
Mary
The price is AU$248
includes taxes & fees
20 Oct - 21 Oct
First Floor Studio Apartment in Historic Chestertown
Indoor pool
Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
2.5 star property
9.2 out of 10, Wonderful, (630)
"This was a great relaxing stay"
United States
Pamela
The price is AU$203
includes taxes & fees
13 Nov - 14 Nov
Holiday Inn Express & Suites Middletown by IHG
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1010)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
United States
Jamijha
The price is AU$144
includes taxes & fees
3 Nov - 4 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool
Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott Middletown
2.5 star property
9.2 out of 10, Wonderful, (295)
"One of the best hotels I have ever stayed "
United States
jean
The price is AU$184
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Middletown
Seasonal outdoor pool
La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
9.0 out of 10, Wonderful, (1011)
"Loved our stay! Will visit again soon!!! "
United States
Meagan
The price is AU$152
includes taxes & fees
26 Oct - 27 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Seasonal outdoor pool, pool umbrellas
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
8.8 out of 10, Excellent, (1006)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is AU$145
includes taxes & fees
3 Nov - 4 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (584)
"This Hotel was excellent in all ways. "
United States
Denny
The price is AU$168
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Baltimore/Aberdeen
Property amenity
Comfort Inn & Suites Aberdeen near APG
Comfort Inn & Suites Aberdeen near APG
2.5 star property
7.8 out of 10, Good, (782)
"The front desk staff were friendly and welcoming!"
United States
Bonnie
The price is AU$152
includes taxes & fees
21 Oct - 22 Oct
Comfort Inn & Suites Aberdeen near 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
"Nice place to stay"
Patrick 1-night trip
Posted 8 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Frequently asked questions

What are some accommodation options 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: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Baltimore Cruise Terminal. Offers buffet, 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.