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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Best Western Plus Easton Inn 8708 Alicia Dr., Easton, MD 21601 ~11.09 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor swimming pool & hot tub
  • 3 star property
From$107
Excellent 5.0 /5Latest Reviews Call
Best Western Denton Inn - Denton 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • Has swimming pool
  • 3 star Highway hotel
From$70
Very Good 4.0 /5Reviews Call
Holiday Inn Express Easton : 8561 Ocean Gateway 8561 Ocean Gateway, Easton, MD 21601 ~11.34 miles south of Eastern Chesapeake Shore
  • Has swimming pool: Indoor Pool & Whirlpool9:00am-11:00pm
  • 3 star Downtown hotel
From$108
Very Good 4.5 /5Recent Reviews Call
Comfort Inn Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Pool available: 9:00am-9:00pmOutdoor Pool
  • Economy Rural hotel
Hilton Garden Inn Kent Island - Grasonville 3206 Main St., Grasonville, MD 21638 ~12.03 miles west of Eastern Chesapeake Shore
  • Pool details: Indoor pool open daily 6 AM-10PM
  • Midscale Riverfront property
From$137
Very Good 4.5 /5Reviews Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~12.17 miles west of Eastern Chesapeake Shore
  • Pool details: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Two star 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
  • Low Cost Downtown hotel
From$119
Very Good 4.5 /5Guest Reviews Call
Harbourtowne Golf Resort & Conference Center 9784 Martingham Dr., Saint Michaels, MD 21663 ~14.45 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel: May - SeptemberOlympic Size Outdoor Pool with Lifeguard
  • Affordable Riverfront hotel
From$99
Average 3.5 /5Reviews Call
St. Michaels Inn - St. Michaels 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Three Star Resort hotel
The Inn at Perry Cabin
+1-800-997-5148
308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • 4 star Resort hotel
From$245
Very Good 4.5 /5Read Reviews Call
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd. 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool available: Indoor heated pool. Open 8am-10pm
  • 3 star Suburban property
From$115
Very Good 4.0 /5Review Score Call
Knapp's Narrows Marina & Inn - Tilghman Island 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~22.95 miles southwest of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Luxury 5 star Oceanfront property
Harrison's Chesapeake House : 21551 Chesapeake House Dr. 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.18 miles southwest of Eastern Chesapeake Shore
  • Has a pool!
  • Low priced 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
  • Pool in hotel: We have an outdoor pool the hrs are 9a-9p
  • 3 star hotel
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~26.20 miles west of Eastern Chesapeake Shore
  • Has swimming pool: indoor pool. lifeguard on duty. hours vary based upon season
  • Four-star Downtown hotel
From$130
Very Good 4.0 /5Recent Reviews Call
Hyatt Regency Chesapeake Bay - Cambridge
+1-800-230-4134
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Has a pool!
  • Expensive hotel
From$219
Very Good 4.0 /5Guest Reviews Call
Holiday Inn Express Cambridge Md in Cambridge 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Includes a pool
  • 3-star Rural hotel
Crowne Plaza - Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~28.29 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 10. Hours vary based on MD laws that require a lifeguard on duty. Higher demand dates have longer hours.
  • 4 star Suburban property
From$109
Average 3.5 /5Reviews Call
Hampton Inn & Suites Annapolis - Annapolis 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Pool available: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Mid-scale Suburban property
Best Western 2520 Riva Rd., Annapolis, MD 21401 ~28.53 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 3-star Suburban property
Springhill Suites by Marriott Annapolis in Annapolis 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
  • Mid-scale Suburban hotel
Annapolis Courtyard by Marriott in Annapolis 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Has a pool!
  • 3 star Downtown hotel
Hilton Garden Inn Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~28.89 miles west of Eastern Chesapeake Shore
  • Has swimming pool: We have an outdoor pool. We open it on Memorial Day and close it on Labor Day.
  • Affordable property
Country Inn & Suites 2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Three Star Suburban hotel
Hampton Inn : 22871 Sussex Highway 22871 Sussex Highway, Seaford, DE 19973 ~29.59 miles southeast of Eastern Chesapeake Shore
  • With a pool!
  • Affordable Rural property
From$107
Very Good 4.5 /5Hotel Reviews Call
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