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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Sleep Inn
+1-888-690-5281
101 Vfw Ave., Grasonville, MD 21638 ~10.11 miles west of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Low priced Resort hotel
Best Western Plus Easton Inn & Suites - Easton 8708 Alicia Dr., Easton, MD 21601 ~11.03 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor swimming pool & hot tub
  • Affordable Rural hotel
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • We have a pool
  • Three Star Highway property
  • Vibe was good
  • Fantastic service
Holiday Inn Express 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 hotel
From$100
Very Good 4.5 /5Recent Reviews CallBookMore Details
Quality Inn Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Pool in hotel: 9:00am-9:00pmOutdoor Pool
  • Excellent pool
  • Great pool
  • Pool was pleasant and refreshing
  • Pool was great
  • Inexpensive Rural property
From$80
Very Good 4.0 /5Reviews CallBookMore Details
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~12.03 miles west of Eastern Chesapeake Shore
  • Pool in hotel: Indoor pool open daily 6 AM-10PM
  • Midscale Riverfront property
From$124
Very Good 4.5 /5Latest Reviews CallBookMore Details
Best Western Kent Narrows Inn in Grasonville 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.
  • Economical Resort property
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
  • Low Cost Downtown hotel
From$115
Very Good 4.5 /5Hotel Reviews CallBookMore Details
St. Michaels Inn in St. Michaels 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
  • Three Star Resort hotel
The Inn at Perry Cabin
+1-800-230-4134
308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Expensive Resort property
From$150
Very Good 4.5 /5Read Reviews CallBookMore Details
Historic Kent Manor Inn - Stevensville 500 Kent Manor Dr., Stevensville, MD 21666 ~16.23 miles west of Eastern Chesapeake Shore
  • With a pool!
  • Expensive Riverfront hotel
From$200
Very Good 4.5 /5Hotel Reviews CallBookMore Details
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool in hotel: Indoor heated pool. Open 8am-10pm
  • Affordable Suburban hotel
Harrison's Chesapeake House 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.18 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel: Memorial Day thru Labor Day outside pool25000 gallons
  • Economical Riverfront hotel
Holiday Inn Express & Suites : 17271 South Dupont Highway 17271 South Dupont Highway, Harrington, DE 19952 ~24.35 miles east of Eastern Chesapeake Shore
  • Includes a pool: We have an outdoor pool the hrs are 9a-9p
  • 3 star property
The Westin 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
  • Expensive Downtown property
From$112
Very Good 4.0 /5Read Reviews CallBookMore Details
Hyatt Regency Chesapeake Bay
+1-800-997-5149
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • We have a pool
  • Pool is good
  • Great pool
  • Great adults only pool
  • Stunning pools
  • Clean pool
  • High-end hotel
From$149
Very Good 4.0 /5Read 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
  • Includes a pool
  • Three Star Rural hotel
Days Inn & Suites Cambridge : 2917 Ocean Gateway 2917 Ocean Gateway, Cambridge, MD 21613 ~27.11 miles south of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Economy Highway property
From$75
Average 3.5 /5Reviews CallBookMore Details
Crowne Plaza 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
  • Mid-scale Suburban property
Best Western Annapolis in Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~28.51 miles west of Eastern Chesapeake Shore
  • Includes a pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 3 star Suburban hotel
From$69
Average 3.5 /5Reviews CallBookMore Details
Hampton Inn & Suites Annapolis in Annapolis 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Includes a pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Midscale Suburban hotel
Springhill Suites by Marriott Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.62 miles west of Eastern Chesapeake Shore
  • Pool in hotel: 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
  • Three Star Suburban hotel
Annapolis Courtyard by Marriott - Annapolis 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Mid-scale Downtown property
From$79
Very Good 4.0 /5Review Score CallBookMore Details
Hilton Garden Inn Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~28.89 miles west of Eastern Chesapeake Shore
  • Pool available: 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
  • 3-star hotel
Country Inn & Suites : 2600 Housley Rd. 2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • Pool in hotel
  • My kids loved the pool
  • 3 star Suburban hotel
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