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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Best Western Plus Easton Inn & Suites in Easton 8708 Alicia Dr., Easton, MD 21601 ~11.09 miles south of Eastern Chesapeake Shore
  • Has swimming pool: Indoor swimming pool & hot tub
  • Mid-scale Rural hotel
From$92
Excellent 5.0 /5Review Score Call
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • With a pool!
  • 3-star Highway hotel
  • Value below average
  • Great room
Holiday Inn Express Easton - Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.34 miles south of Eastern Chesapeake Shore
  • Pool in hotel: Indoor Pool & Whirlpool9:00am-11:00pm
  • Excellent pool
  • Great pool
  • Indoor pool was a lot of
  • Nice pool
  • 3-star Downtown property
From$105
Very Good 4.5 /5Review Score Call
Comfort Inn Easton - Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Has swimming pool: 9:00am-9:00pmOutdoor Pool
  • Excellent pool
  • Great pool
  • Pool was pleasant and refreshing
  • Pool was great
  • Cheap Rural hotel
From$80
Very Good 4.0 /5Read Reviews Call
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~12.03 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor pool open daily 6 AM-10PM
  • Affordable Riverfront property
From$124
Very Good 4.5 /5Guest Reviews Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~12.17 miles west of Eastern Chesapeake Shore
  • Includes a pool: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Low priced Resort hotel
Hampton Inn : 8058 Ocean Gateway 8058 Ocean Gateway, Easton, MD 21601 ~12.29 miles south of Eastern Chesapeake Shore
  • Pool details: Pool Hours 6am to 10pm
  • Inexpensive Downtown hotel
From$119
Very Good 4.5 /5Hotel Reviews Call
Harbourtowne Golf Resort & Conference Center : 9784 Martingham Dr. 9784 Martingham Dr., Saint Michaels, MD 21663 ~14.45 miles southwest of Eastern Chesapeake Shore
  • Includes a pool: May - SeptemberOlympic Size Outdoor Pool with Lifeguard
  • Mid-scale Riverfront hotel
St. Michaels Inn : 1228 South Talbot St. 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Pool available: 8 am to 9 pm open seasonal
  • Great pool
  • Pool is good
  • Pool nice
  • Clean pool
  • Mid-scale Resort property
The Inn at Perry Cabin - St. Michael's
+1-800-230-4134
308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • Has a pool!
  • 4 star Resort hotel
From$150
Very Good 4.5 /5Recent Reviews Call
Holiday Inn Express & Suites Chestertown Md in Chestertown 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool details: Indoor heated pool. Open 8am-10pm
  • 3 star Suburban hotel
From$162
Very Good 4.0 /5Guest Reviews Call
Knapp's Narrows Marina & Inn 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~22.95 miles southwest of Eastern Chesapeake Shore
  • Has a pool!
  • Luxurious Five Star Oceanfront hotel
Harrison's Chesapeake House in Tilghman 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.18 miles southwest of Eastern Chesapeake Shore
  • Includes a pool: Memorial Day thru Labor Day outside pool25000 gallons
  • Cheap Riverfront property
Holiday Inn Express & Suites 17271 South Dupont Highway, Harrington, DE 19952 ~24.35 miles east of Eastern Chesapeake Shore
  • Pool in hotel: We have an outdoor pool the hrs are 9a-9p
  • Affordable property
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~26.20 miles west of Eastern Chesapeake Shore
  • Pool available: indoor pool. lifeguard on duty. hours vary based upon season
  • Horrible pool
  • Pool should be renewed
  • No outdoor pool
  • Pool did not open
  • High-end Downtown property
From$112
Very Good 4.0 /5Recent Reviews Call
Hyatt Regency Chesapeake Bay - Cambridge
+1-800-997-5149
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Pool is good
  • Great pool
  • Great adults only pool
  • Stunning pools
  • Clean pool
  • Expensive hotel
From$189
Very Good 4.0 /5Recent Reviews Call
Holiday Inn Express Cambridge Md - Cambridge 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Has a pool!
  • Midscale Rural property
From$109
Very Good 4.0 /5Latest Reviews Call
Days Inn & Suites Cambridge - Cambridge 2917 Ocean Gateway, Cambridge, MD 21613 ~27.11 miles south of Eastern Chesapeake Shore
  • Includes a swimming pool
  • 2-star Highway hotel
Crowne Plaza 173 Jennifer Rd., Annapolis, MD 21401 ~28.29 miles west of Eastern Chesapeake Shore
  • Pool available: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Also large whirlpool tht seats 10. Hours vary based on MD laws that require a lifeguard on duty. Higher demand dates have longer hours.
  • Moderately clean pool area
  • About half of guests thought the pool was clean
  • Midscale Suburban property
Hampton Inn & Suites Annapolis - Annapolis 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Pool in hotel: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Midscale Suburban hotel
Best Western : 2520 Riva Rd. 2520 Riva Rd., Annapolis, MD 21401 ~28.53 miles west of Eastern Chesapeake Shore
  • Pool available: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 3-star Suburban property
Springhill Suites by Marriott Annapolis : 189 Admiral Cochrane Dr. 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.62 miles west of Eastern Chesapeake Shore
  • Includes a pool: Indoor Swimming Pool with WhirlpoolWeekdays: 5pm-10pmFridays: 3pm - 10pmWeekends: 10am - 10pmSummer: 10am - 10pm daily
  • Pool is below average
  • Pool should be renewed
  • Pool is small
  • Pool was very chilly
  • Pool water was very cold
  • Mid-scale Suburban property
From$79
Very Good 4.5 /5Reviews Call
Annapolis Courtyard by Marriott : 2559 Riva Rd. 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Mid-scale Downtown property
Hilton Garden Inn Annapolis : 305 Harry South Truman 305 Harry South Truman, Annapolis, MD 21401 ~28.89 miles west of Eastern Chesapeake Shore
  • Pool details: We have an outdoor pool. We open it on Memorial Day and close it on Labor Day.
  • Horrible pool
  • Pool should be renewed
  • No indoor pool
  • Swimming pool was not open
  • No pool
  • Midscale hotel
Country Inn & Suites 2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • Pool in hotel
  • My kids loved the pool
  • Mid-scale Suburban hotel
From$75
Very Good 4.0 /5Read Reviews Call
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