Hotels with Swimming Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Swimming Pool

Our top choices for Chestertown hotels with a pool

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very Good, (81 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
"beautiful pool…."
United States
Stephen
The price is P8,166
P9,336 total
includes taxes & fees
May 19 - May 20
The Lodge at Great Oak Landing

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (911 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
"Sorry pool was closed"
United States
Anita
The price is P6,651
P7,383 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Inn & Suites Chestertown

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
"The pool, hot tub, and sauna were exactly the kind of decompressing I needed."
United States
Elizabeth-Ann
The price is P6,943
P7,707 total
includes taxes & fees
May 17 - May 18
Best Western Kent Narrows Inn

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
"Pool was great"
United States
Cristy
The price is P10,991
P12,200 total
includes taxes & fees
May 17 - May 18
Inn at Huntingfield Creek

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,002 reviews)
  • cleanliness
    Dip into poolside bliss at this hotel with a sun-soaked outdoor pool and modern fitness center nearby.
"Comfortable bed, quiet room. Nice little swimming pool, just enough to cool off or do a little exercise in the summer heat. There’s a really nice brew pub about 2 miles away, there’s a grocery store across the parking lot. And it’s just 15 minutes drive from the fabulous Bombay Hook National Wildlife Refuge where we were birding. And the staff was really nice."
United States
Frances
The price is P5,341
P5,929 total
includes taxes & fees
May 25 - May 26
Quality Inn Smyrna

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
  • cleanliness
    Splash into waterfront bliss with indoor and outdoor pools at this log cabin retreat.
"This is a cute little cabin. The room was as advertised. The place is also a Christian ministry place. Hotels.com guests should be aware that there are signs on the road in that reference Jesus. We also saw a couple prayer circles. This was not a problem for us. It waa early season so the lovely pools were not open. They send an email with check in directions which were use the lock box. We did not get the email. We went to what looked like a check in area and no one was around. This was quite...
United States
mary
The price is P21,591
P26,158 total
includes taxes & fees
May 21 - May 22
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (653 reviews)
  • cleanliness
    Plunge into tranquil waters at this hotel's refreshing indoor pool for a serene aquatic escape.
"I had a great stay at the Hilton Garden Inn Aberdeen last month (Aug 2022). The staff was great the room and facilities (breakfast dining and pool) were first class, and the location was perfect, near to a variety of restaurants, places of business, and a church for Sunday Mass. It all made for a very comfortable and enjoyable stay."
United States
John
The price is P6,529
P7,312 total
includes taxes & fees
May 27 - May 28
Hilton Garden Inn Aberdeen

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (387 reviews)
  • cleanliness
    Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
"The pool was small but did the trick."
United States
Richard
The price is P6,419
P7,125 total
includes taxes & fees
May 31 - Jun 1
Fairfield Inn & Suites by Marriott Middletown

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (648 reviews)
  • cleanliness
    Revitalizing dips await at this indoor pool sanctuary with attentive staff and plush amenities.
"We were in and out pretty quickly but it was a really nice clean property the staff was helpful it was good to have some snacks available in the lobby there was a pool table in the lobby which is nice and comfortable chairs and an easy place to hang out they served a very nice breakfast in the morning so all good"
United States
Thomas
The price is P5,820
P6,519 total
includes taxes & fees
May 25 - May 26
Hampton Inn & Suites Baltimore/Aberdeen
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.

Choose what matters most at hotels with a pool in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

What are some accommodations 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 Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Inner Harbor Marina. Features 2 bars, a seasonal outdoor pool, and spa services. Hampton Inn Baltimore/Glen Burnie: Offers complimentary wired internet access, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Rolphs Wharf Marina, Historical Society of Kent County Maryland, 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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