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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Sleep Inn Grasonville
+1-888-690-5247
101 Vfw Ave., Grasonville, MD 21638 ~10.07 miles west of Eastern Chesapeake Shore
  • Pool in hotel
  • Two star Resort property
Best Western Plus Easton Inn & Suites 8708 Alicia Dr., Easton, MD 21601 ~11.04 miles south of Eastern Chesapeake Shore
  • Includes a pool: Indoor swimming pool & hot tub
  • 3-star Rural property
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • Includes a swimming pool
  • 3-star Highway hotel
  • Fantastic service
  • Moderately clean hotel facilities
From$70
Very Good 4.0 /5Reviews CallBookMore Details
Holiday Inn Express Easton - Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.34 miles south of Eastern Chesapeake Shore
  • Has swimming pool: Indoor Pool & Whirlpool9:00am-11:00pm
  • Excellent pool
  • Great pool
  • Indoor pool was a lot of
  • Nice pool
  • Affordable Downtown property
Quality Inn Easton : 8523 Ocean Gateway 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
  • 2-star Rural hotel
Hilton Garden Inn Kent Island in Grasonville 3206 Main St., Grasonville, MD 21638 ~12.03 miles west of Eastern Chesapeake Shore
  • Pool details: Indoor pool open daily 6 AM-10PM
  • Three Star Riverfront hotel
From$124
Very Good 4.5 /5Latest Reviews CallBookMore Details
Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 ~12.14 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • 2-star Resort property
Hampton Inn in Easton 8058 Ocean Gateway, Easton, MD 21601 ~12.29 miles south of Eastern Chesapeake Shore
  • Has swimming pool: Pool Hours 6am to 10pm
  • Economy Downtown property
From$115
Very Good 4.5 /5Review Score CallBookMore Details
St. Michaels Inn : 1228 South Talbot St. 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Has swimming pool: 8 am to 9 pm open seasonal
  • Great pool
  • Pool is good
  • Pool nice
  • Clean pool
  • 3 star Resort hotel
The Inn at Perry Cabin
+1-800-881-1523
308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Luxury 5 star Resort property
From$150
Very Good 4.5 /5Reviews CallBookMore Details
Historic Kent Manor Inn 500 Kent Manor Dr., Stevensville, MD 21666 ~16.23 miles west of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Four-star Riverfront hotel
From$190
Very Good 4.5 /5Latest Reviews CallBookMore Details
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool details: Indoor heated pool. Open 8am-10pm
  • Mid-scale Suburban property
From$95
Very Good 4.0 /5Review Score CallBookMore Details
Harrison's Chesapeake House 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
  • Low priced Riverfront property
Holiday Inn Express & Suites 17271 South Dupont Highway, Harrington, DE 19952 ~24.35 miles east of Eastern Chesapeake Shore
  • Has swimming pool: We have an outdoor pool the hrs are 9a-9p
  • Midscale property
The Westin Annapolis - Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~26.20 miles west of Eastern Chesapeake Shore
  • Pool details: 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 /5Review Score CallBookMore Details
Hyatt Regency Chesapeake Bay 100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Has swimming pool
  • Pool is good
  • Great pool
  • Great adults only pool
  • Stunning pools
  • Clean pool
  • 4-star property
From$149
Very Good 4.0 /5Latest Reviews CallBookMore Details
Holiday Inn Express Cambridge Md : 2715 Ocean Gateway 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Has swimming pool
  • Mid-scale Rural property
From$99
Very Good 4.0 /5Read Reviews CallBookMore Details
Days Inn & Suites Cambridge in Cambridge 2917 Ocean Gateway, Cambridge, MD 21613 ~27.11 miles south of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Cheap Highway property
Crowne Plaza - Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~28.29 miles west of Eastern Chesapeake Shore
  • Has swimming pool: 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
  • Three Star Suburban hotel
Hampton Inn & Suites Annapolis 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3-star Suburban hotel
From$75
Very Good 4.0 /5Review Score CallBookMore Details
Best Western Annapolis : 2520 Riva Rd. 2520 Riva Rd., Annapolis, MD 21401 ~28.56 miles west of Eastern Chesapeake Shore
  • Pool details: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 3-star Suburban property
Springhill Suites by Marriott Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.62 miles west of Eastern Chesapeake Shore
  • Pool details: 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
  • Affordable Suburban property
Annapolis Courtyard by Marriott 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Has a pool!
  • Midscale Downtown hotel
Hilton Garden Inn Annapolis - Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~28.89 miles west of Eastern Chesapeake Shore
  • Includes a pool: 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
  • Affordable 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
  • Affordable Suburban property
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