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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Sleep Inn Grasonville 101 Vfw Ave., Grasonville, MD 21638 ~10.06 miles west of Eastern Chesapeake Shore
  • Includes a swimming pool
  • Low-priced Resort hotel
Best Western Plus Easton Inn & Suites 8708 Alicia Dr., Easton, MD 21601 ~11.02 miles south of Eastern Chesapeake Shore
  • Pool details: Indoor swimming pool & hot tub
  • Affordable Rural property
From$88
Excellent 5.0 /5Review Score CallBookMore Details
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629 ~11.09 miles east of Eastern Chesapeake Shore
  • We have a pool
  • Midscale Highway property
From$80
Very Good 4.0 /5Reviews CallBookMore Details
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.32 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor Pool & Whirlpool9:00am-10:00pm
  • Excellent pool
  • Great pool
  • Indoor pool was a lot of
  • Nice pool
  • Mid-scale Rural property
From$105
Very Good 4.5 /5Reviews CallBookMore Details
Quality Inn Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.37 miles south of Eastern Chesapeake Shore
  • Pool details: 9:00am-9:00pmOutdoor Pool
  • Excellent pool
  • Great pool
  • Pool was pleasant and refreshing
  • Pool was great
  • Economy Rural property
From$75
Very Good 4.0 /5Reviews CallBookMore Details
Holiday Inn Express Annapolis East / Kent Island - Grasonville 1020 Kent Narrows Rd., Grasonville, MD 21638 ~11.92 miles west of Eastern Chesapeake Shore
  • We have a pool
  • Mid-scale Rural property
From$180
Very Good 4.0 /5Latest Reviews CallBookMore Details
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~12.01 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor pool open daily 6 AM-10PM
  • Affordable Riverfront hotel
From$136
Very Good 4.5 /5Review Score CallBookMore Details
Best Western Kent Narrows Inn - Grasonville 3101 Main St., Grasonville, MD 21638 ~12.13 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Cheap Resort hotel
Hampton Inn : 8058 Ocean Gateway 8058 Ocean Gateway, Easton, MD 21601 ~12.27 miles south of Eastern Chesapeake Shore
  • Includes a pool: Pool Hours 6am to 10pm
  • 2-star Downtown hotel
From$109
Very Good 4.5 /5Latest Reviews CallBookMore Details
St. Michaels Inn in St. Michaels 1228 South Talbot St., St. Michaels, MD 21663 ~15.74 miles southwest of Eastern Chesapeake Shore
  • Pool details: 8 am to 9 pm open seasonal
  • Great pool
  • Pool is good
  • Pool nice
  • Clean pool
  • Mid-scale Resort hotel
From$72
Average 3.5 /5Reviews CallBookMore Details
The Inn at Perry Cabin
+1-888-283-3404
308 Watkins Lane, St. Michael's, MD 21663 ~15.78 miles southwest of Eastern Chesapeake Shore
  • Has a pool!
  • Luxurious Five Star Resort property
From$150
Very Good 4.5 /5Review Score CallBookMore Details
Historic Kent Manor Inn : 500 Kent Manor Dr. 500 Kent Manor Dr., Stevensville, MD 21666 ~16.21 miles west of Eastern Chesapeake Shore
  • Includes a pool: Outdoor (seasonal pool)
  • High end Riverfront hotel
From$225
Very Good 4.5 /5Recent Reviews CallBookMore Details
Holiday Inn Expres & Suites in Chestertown 150 Scheeler Rd., Chestertown, MD 21620 ~19.70 miles north of Eastern Chesapeake Shore
  • Pool available: Indoor heated pool. Open 8am-10pm
  • Mid-scale Suburban hotel
From$79
Very Good 4.0 /5Reviews CallBookMore Details
Knapp's Narrows Marina & Inn : 6176 Tilghman Island Rd. 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~22.90 miles southwest of Eastern Chesapeake Shore
  • With a pool!
  • Luxury Five Star Oceanfront hotel
Harrison's Chesapeake House 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.12 miles southwest of Eastern Chesapeake Shore
  • Has swimming pool: Memorial Day thru Labor Day outside pool25000 gallons
  • 3 star Riverfront property
From$99
Very Good 4.5 /5Review Score CallBookMore Details
Holiday Inn Express & Suites in Harrington 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
  • 3 star hotel
From$80
Very Good 4.5 /5Read Reviews CallBookMore Details
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~26.17 miles west of Eastern Chesapeake Shore
  • Has swimming pool: indoor pool. lifeguard on duty. hours vary based upon season
  • Horrible pool
  • Pool should be renewed
  • No outdoor pool
  • Pool did not open
  • Four star Downtown property
From$139
Very Good 4.0 /5Guest Reviews CallBookMore Details
Hyatt Regency Chesapeake Bay in Cambridge 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 property
From$159
Very Good 4.0 /5Recent Reviews CallBookMore Details
Crowne Plaza in Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~28.23 miles west of Eastern Chesapeake Shore
  • Pool in hotel: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Also large whirlpool tht seats 6. Hours vary.
  • High end Suburban property
Hampton Inn & Suites Annapolis : 124 Womack Dr. 124 Womack Dr., Annapolis, MD 21401 ~28.48 miles west of Eastern Chesapeake Shore
  • Pool available: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Affordable Suburban property
Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 3 star Suburban property
From$89
Average 3.5 /5Reviews CallBookMore Details
Springhill Suites by Marriott Annapolis in Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.58 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Indoor Swimming Pool with Whirlpool Spa Tub and Outdoor Patio AreaDaily from 10:00am - 10:00pm (No lifeguard on duty)
  • Pool is below average
  • Pool should be renewed
  • Pool is small
  • Pool was very chilly
  • Pool water was very cold
  • 3 star Suburban property
Hilton Garden Inn Annapolis in Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~28.85 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
  • Three Star property
Country Inn & Suites - Annapolis 2600 Housley Rd., Annapolis, MD 21401 ~29.00 miles west of Eastern Chesapeake Shore
  • Includes a pool: Indoor heated pool open Monday - Friday 5pm - 10pm and Saturday and Sunday 10am - 10pm
  • My kids loved the pool
  • Midscale Suburban property
From$85
Very Good 4.0 /5Review Score CallBookMore Details
Hilton Garden Inn Dover in Dover 1706 North Dupont Highway, Dover, DE 19901 ~30.35 miles northeast of Eastern Chesapeake Shore
  • Pool in hotel: Indoor pool and hot tub open daily 6am-10pm
  • Three Star Suburban property
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