
Find Hotels with a Pool in Chestertown, MD
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Check availability on Chestertown Hotels with a Pool
Tonight
Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our top choices for Chestertown hotels with a pool




1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
- Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
$104 nightly
$115 total
Sep 20 - Sep 21
Total with taxes and fees




2. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
- Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
$122 nightly
$135 total
Sep 2 - Sep 3
Total with taxes and fees




3. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
- Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
$144 nightly
$159 total
Sep 2 - Sep 3
Total with taxes and fees




4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
$273 nightly
$289 total
Sep 8 - Sep 9
Total with taxes and fees




5. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees




6. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
- Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
$200 nightly
$223 total
Sep 7 - Sep 8
Total with taxes and fees




7. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
- Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
$100 nightly
$111 total
Sep 28 - Sep 29
Total with taxes and fees




8. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
- Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
$116 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
View all properties
Top Chestertown Hotel Reviews
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"The amazing staff , the room was awesome definitely staying here again already recommended to a few friends that travel to NC for a break back to NY like we did , actually went to the mall and loved it doing it again thank you for your amazing service"
Best Western Kent Narrows Inn
8/10 Good
"Location was great, beds were comfortable and the room was clean."
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"Great view of the water."
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
10/10 Excellent
"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."
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