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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Sleep Inn Grasonville in Grasonville
+1-888-690-5247
101 Vfw Ave., Grasonville, MD 21638 ~10.06 miles west of Eastern Chesapeake Shore
  • We have a pool ready for use
  • Economy Resort hotel
From$60
Average 3.5 /5 Reviews Call BookMore Details
Best Western Plus Easton Inn & Suites - Easton 8708 Alicia Dr., Easton, MD 21601 ~11.02 miles south of Eastern Chesapeake Shore
  • Pool in hotel: Indoor swimming pool & hot tub
  • Affordable Rural hotel
From$92
Excellent 5.0 /5 Reviews Call BookMore Details
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.32 miles south of Eastern Chesapeake Shore
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-11:00pm
  • Excellent pool
  • Great pool
  • Indoor pool was a lot of
  • Nice pool
  • Affordable Downtown hotel
From$95
Very Good 4.5 /5 Review Score Call BookMore Details
Quality Inn Easton - Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.37 miles south of Eastern Chesapeake Shore
  • Has swimming pool: 9:00am-9:00pm Outdoor Pool
  • Excellent pool
  • Great pool
  • Pool was pleasant and refreshing
  • Pool was great
  • Cheap Rural hotel
From$85
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Kent Island - Grasonville 3206 Main St., Grasonville, MD 21638 ~12.01 miles west of Eastern Chesapeake Shore
  • Includes a pool: Indoor pool open daily 6 AM-10PM
  • Mid-scale Riverfront hotel
From$124
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 ~12.13 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Cheap Resort property
From$72
Average 3.5 /5 Review Score Call BookMore Details
Hampton Inn : 8058 Ocean Gateway 8058 Ocean Gateway, Easton, MD 21601 ~12.27 miles south of Eastern Chesapeake Shore
  • Pool details: Pool Hours 6am to 10pm
  • Cheap Downtown hotel
From$115
Very Good 4.5 /5 Read Reviews Call BookMore Details
St. Michaels Inn in St. Michaels 1228 South Talbot St., St. Michaels, MD 21663 ~15.74 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 hotel
From$55
Average 3.5 /5 Latest Reviews Call BookMore Details
The Inn at Perry Cabin
+1-888-305-3366
308 Watkins Lane, St. Michael's, MD 21663 ~15.78 miles southwest of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Luxurious Five Star Resort property
From$150
Very Good 4.5 /5 Reviews Call BookMore Details
Historic Kent Manor Inn - Stevensville 500 Kent Manor Dr., Stevensville, MD 21666 ~16.21 miles west of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Four star Riverfront hotel
From$190
Very Good 4.5 /5 Reviews Call BookMore Details
Holiday Inn Express & Suites Chestertown Md - Chestertown 150 Scheeler Rd., Chestertown, MD 21620 ~19.75 miles north of Eastern Chesapeake Shore
  • Includes a pool: Indoor heated pool. Open 8am-10pm
  • 3 star Suburban property
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Harrison's Chesapeake House : 21551 Chesapeake House Dr. 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.12 miles southwest of Eastern Chesapeake Shore
  • Includes a pool: Memorial Day thru Labor Day outside pool 25000 gallons
  • Affordable Riverfront property
Holiday Inn Express & Suites : 17271 South Dupont Highway 17271 South Dupont Highway, Harrington, DE 19952 ~24.31 miles east of Eastern Chesapeake Shore
  • Includes a pool: We have an outdoor pool the hrs are 9a-9p
  • Midscale hotel
From$79
Very Good 4.5 /5 Review Score Call BookMore Details
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~26.17 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 /5 Read Reviews Call BookMore Details
Hyatt Regency Chesapeake Bay 100 Heron Blvd., Cambridge, MD 21613 ~26.47 miles south of Eastern Chesapeake Shore
  • With a pool!
  • Pool is good
  • Great pool
  • Great adults only pool
  • Stunning pools
  • Clean pool
  • 4-star hotel
From$149
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Cambridge Md 2715 Ocean Gateway, Cambridge, MD 21613 ~26.82 miles south of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Three Star Rural property
From$99
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Days Inn & Suites Cambridge 2917 Ocean Gateway, Cambridge, MD 21613 ~27.07 miles south of Eastern Chesapeake Shore
  • We have a pool ready for use
  • Inexpensive Highway property
From$60
Average 3.5 /5 Review Score Call BookMore Details
Crowne Plaza 173 Jennifer Rd., Annapolis, MD 21401 ~28.26 miles west of Eastern Chesapeake Shore
  • Includes a 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 property
From$109
Average 3.5 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Annapolis in Annapolis 124 Womack Dr., Annapolis, MD 21401 ~28.48 miles west of Eastern Chesapeake Shore
  • Pool details: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Three Star Suburban hotel
From$75
Very Good 4.0 /5 Read Reviews Call BookMore Details
Best Western Annapolis in Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Pool details: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Three Star Suburban property
From$69
Average 3.5 /5 Read Reviews Call BookMore Details
Springhill Suites by Marriott Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.58 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor Swimming Pool with Whirlpool Weekdays: 5pm-10pm Fridays: 3pm - 10pm Weekends: 10am - 10pm Summer: 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 hotel
From$79
Very Good 4.5 /5 Read Reviews Call BookMore Details
Annapolis Courtyard by Marriott : 2559 Riva Rd. 2559 Riva Rd., Annapolis, MD 21401 ~28.70 miles west of Eastern Chesapeake Shore
  • Has a pool!
  • 3 star Downtown hotel
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Annapolis in Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~28.85 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
  • 3-star property
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Country Inn & Suites 2600 Housley Rd., Annapolis, MD 21401 ~29.00 miles west of Eastern Chesapeake Shore
  • Includes a swimming pool
  • My kids loved the pool
  • 3 star Suburban property
From$75
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover 1706 North Dupont Highway, Dover, DE 19901 ~30.35 miles northeast of Eastern Chesapeake Shore
  • Includes a pool: Indoor pool and hot tub open daily 6am-10pm
  • Midscale Suburban hotel
From$84
Very Good 4.5 /5 Review Score Call BookMore Details
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