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Chestertown Hotels with Swimming Pool

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
8 Jul - 9 Jul
Tomorrow
9 Jul - 10 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Top Chestertown Hotels with Swimming Pools

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (53)
"Great little gem in the middle of nowhere….beautiful
pool
….private beach…great restaurant….free golf course on the property too!!…what else can you ask for….10 stars😀"
Stephen
The price is RM560
RM622 total
includes taxes & fees
9 Jul - 10 Jul
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (777)
"Great stay. Sorry
pool
was closed "
Anita
The price is RM481
RM534 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown
Quality Inn
Property amenity

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"Well I have to start by saying that the check in was fast and easy the front clerk was a young man very polite and nice so the greeting was welcoming. The room was nice and clean and smelled good. My kids so very much enjoyed the
pool
that was also clean e ended booking the hotel another nite. The breakfast was simple but good. I have to say I'm very pleased and impressed with the hotel and thank you to the young clerk who was attentive and accommodating to my family. Will be coming again."
Evelyn
The price is RM424
RM470 total
includes taxes & fees
27 Jul - 28 Jul
Quality Inn
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (813)
"Great hotel!
Pool
and hot tub was fabulous! Free breakfast which had fruit, cereal, bacon, potatoes, waffels, yogurt and much more! Would come again!"
lisa
The price is RM533
RM591 total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Exterior

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (590)
"All staff were soo kind and cheery! They were helpful and we felt welcome when we came and went at the hotel. Place was very clean, super accommodating. Kids loved the
indoor pool
. "
Aidenn
The price is RM522
RM579 total
includes taxes & fees
4 Aug - 5 Aug
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Lobby

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (247)
"Clean, quiet, friendly staff, great complimentary breakfast. All around a great hotel."
Clarissonia
The price is RM563
RM625 total
includes taxes & fees
27 Jul - 28 Jul
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (784)
"Everything was clean despite a weird odor in the hallway of the first floor. The staff was nice and the
pool
was good. Breakfast was nothing special, but it was good and had a good variety. "
Samantha
The price is RM422
RM468 total
includes taxes & fees
3 Aug - 4 Aug
Quality Inn
Hilton Garden Inn Kent Island Marina
Terrace/patio

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (956)
"The rooms were very comfortable. We had a great view from our balcony. The staff were amazing. We loved the
pool
. The food at the grill could use some improvement. It was a very comfortable and enjoyable trip."
barbara
The price is RM644
RM715 total
includes taxes & fees
20 Jul - 21 Jul
Hilton Garden Inn Kent Island 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.

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: 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 high-speed (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 such as Chestertown Dog Park and Crumpton Auction. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina and Chestertown Historic District 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.