Photo by Patricia Knorr
Find Hotels with a Pool in Chester, MD
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Chester Hotels with a Pool
Compare Chester Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.
Find out more about Chester
Find out more about Chester
Recent reviews of Chester hotels
Recent reviews of Chester hotels

The Westin Annapolis
5/5 Excellent
"Always love our Westin Annapolis stay - can’t wait to see it post construction "
A verified traveler stayed at The Westin Annapolis
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Find More Hotels near Chester
More Accommodation Types in Chester
- 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 Chester Attractions
- Hotels near Chesapeake Exploration Center
- Hotels near U.S. Naval Academy
- Hotels near Chesapeake Bay Bridge
- Hotels near Annapolis City Dock
- Hotels near Sandy Point State Park
- Hotels near Navy-Marine Corps Memorial Stadium
- Hotels near Anne Arundel Medical Center
- Hotels near Westfield Annapolis Mall
- Hotels near St. Michaels Winery
- Hotels near Annapolis Mall Shopping Center
Chester Hotels by Star Rating
Explore more hotels
- Graduate by Hilton Annapolis
- Hampton Inn & Suites Annapolis
- Inn at Perry Cabin
- DoubleTree by Hilton Hotel Annapolis
- Fairfield Inn & Suites By Marriott Annapolis
- Holiday Inn Express & Suites Annapolis by IHG
- Hilton Garden Inn Kent Island Marina
- Best Western Kent Narrows Inn
- St Michaels Inn
- Best Western Annapolis
- The Inn at Chesapeake Bay Beach Club
- Hilton Garden Inn Annapolis
- The Wildset
- Best Western Plus Easton Inn & Suites
- Wylder Tilghman Island
- Holiday Inn Express Annapolis - Kent Island by IHG
- The Tidewater Inn
- 240' Private Beachfront @Kent Island Love Point - Great for Large Groups
- Residence Inn By Marriott Annapolis
- Quality Inn