Photo by Assya A
Find Hotels with a Pool in Chestertown, MD
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check availability on Chestertown Hotels with a Pool
Top Chestertown Hotels with a Pool
Our top choices for Chestertown hotels with a pool

Holiday Inn Express White Marsh by IHG
Holiday Inn Express White Marsh by IHG
9.6 out of 10, Exceptional, (916)
The price is AED 360
AED 416 total
includes taxes & fees
1 Sep - 2 Sep

Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
9.4 out of 10, Exceptional, (1009)
The price is AED 325
AED 364 total
includes taxes & fees
3 Sep - 4 Sep

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
8.8 out of 10, Excellent, (1002)
The price is AED 309
AED 346 total
includes taxes & fees
4 Sep - 5 Sep

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
8.0 out of 10, Very Good, (66)
The price is AED 486
AED 539 total
includes taxes & fees
4 Sep - 5 Sep

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
8.6 out of 10, Excellent, (806)
The price is AED 403
AED 447 total
includes taxes & fees
7 Sep - 8 Sep

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (99)
The price is AED 364
AED 583 total
includes taxes & fees
11 Sep - 12 Sep

Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
9.2 out of 10, Wonderful, (609)
The price is AED 393
AED 436 total
includes taxes & fees
7 Sep - 8 Sep

Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
9.2 out of 10, Wonderful, (894)
The price is AED 511
AED 567 total
includes taxes & fees
22 Sep - 23 Sep
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.
Hotels with private pools in Chestertown

First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (99)
The price is AED 364
AED 583 total
includes taxes & fees
11 Sep - 12 Sep
Hotels with outdoor pools in Chestertown

The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
8.0 out of 10, Very Good, (66)
The price is AED 486
AED 539 total
includes taxes & fees
4 Sep - 5 Sep
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.
Top Chestertown Hotel Reviews
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Find More Hotels near Chestertown
More Hotel Options in Chestertown
- Adventure Hotels in Chestertown
- Beach Hotels in Chestertown
- Business Hotels in Chestertown
- Cheap Hotels in Chestertown
- Family Hotels in Chestertown
- Golf Hotels in Chestertown
- Historic Hotels in Chestertown
- Hotel Wedding Venues in Chestertown
- Hotel with a Concierge in Chestertown
- Hotels with Bars in Chestertown
- Hotels with Free Parking in Chestertown
- Hotels with WiFi in Chestertown
- Hotels with an Indoor Pool in Chestertown
- Hotels with smoking rooms in Chestertown
- Luxury Hotels in Chestertown
- Pet-friendly Hotels in Chestertown
- Resorts & Hotels with Spas in Chestertown
- Romantic Hotels in Chestertown
- Shopping Hotels in Chestertown
More Accommodation Types in Chestertown
- Vacation Homes in Maryland
- Condo Rentals in Maryland
- Apartments in Maryland
- Cottages in Maryland
- Cabin Rentals in Maryland
- Motels in Maryland
- Aparthotels in Maryland
- B&B in Maryland
- Guest Houses in Maryland
- Chalets in Maryland
- Villas in Maryland
- Resorts in Maryland
- Houseboats in Maryland
- Inns in Maryland
- Lodges in Maryland
- Hostels in Maryland
- Condo Resorts in Maryland
- Holiday Park Resorts in Maryland
Hotels near popular Chestertown Attractions
Chestertown Hotels by Star Rating
Explore more hotels
- Hampton Inn & Suites Edgewood/Aberdeen-South
- La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
- Hyatt Place Kent Narrows & Marina
- Annapolis Waterfront Hotel, Autograph Collection
- Fairfield Inn & Suites by Marriott White Marsh
- Hampton Inn Baltimore/White Marsh
- Hampton Inn Baltimore/Glen Burnie
- The Inn at Henderson's Wharf, Ascend Hotel Collection
- Hilton Garden Inn Kent Island Marina
- Best Western Kent Narrows Inn
- SpringHill Suites Baltimore White Marsh/Middle River
- La Quinta Inn & Suites by Wyndham Aberdeen-APG
- Hampton Inn Baltimore Bayview Campus
- Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
- The Inn at Chesapeake Bay Beach Club
- Comfort Inn & Suites Aberdeen near APG
- Holiday Inn Express White Marsh by IHG
- Americas Best Value Inn Edgewood
- Residence Inn by Marriott Baltimore White Marsh
- Holiday Inn Express Aberdeen by IHG