Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a 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
7.8 out of 10, Good, (80 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
"beautiful pool…."
United States
Stephen
The price is NT$4,156
NT$4,752 total
includes taxes & fees
May 14 - May 15
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, (909 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 NT$3,605
NT$4,002 total
includes taxes & fees
May 25 - May 26
Comfort Inn & Suites Chestertown

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 NT$2,872
NT$3,187 total
includes taxes & fees
May 26 - May 27
Quality Inn Smyrna

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,006 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 NT$3,615
NT$4,013 total
includes taxes & fees
May 27 - May 28
Best Western Kent Narrows Inn

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 NT$10,990
NT$13,315 total
includes taxes & fees
May 14 - May 15
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

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 NT$5,669
NT$6,292 total
includes taxes & fees
May 31 - Jun 1
Inn at Huntingfield Creek

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
"Pool, patio and water view!"
United States
Linda
The price is NT$4,210
NT$4,673 total
includes taxes & fees
May 27 - May 28
Holiday Inn Express Annapolis East-Kent Island by IHG

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (338 reviews)
  • cleanliness
    Splash into vacation bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.
"Myself and kids had a great experience "
United States
Jayson
The price is NT$3,440
NT$3,852 total
includes taxes & fees
Jun 9 - Jun 10
Fairfield Inn & Suites by Marriott Aberdeen

Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
2.5 star property
Aberdeen
8.0 out of 10, Very Good, (897 reviews)
  • cleanliness
    Dive into a refreshing seasonal outdoor pool experience at this comfortable Aberdeen hotel with immaculate, newly remodeled rooms.
"A plus was the pool where the boys got to cool off and relax after games."
United States
Gloria
The price is NT$2,403
NT$2,692 total
includes taxes & fees
May 18 - May 19
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.

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 Baltimore Inner Harbor Marina. Provides 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Features complimentary wired internet access, an indoor pool, and free self parking. Hampton Inn Baltimore/Glen Burnie: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access.
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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