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Hotel Name
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Amenities

Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Best Western Plus Easton Inn : 8708 Alicia Dr. 8708 Alicia Dr., Easton, MD 21601 ~11.09 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor swimming pool & hot tub
  • Midscale property
From$107
Excellent 5.0 /5 Recent Reviews Call
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • We have a pool
  • 3 star Highway property
From$70
Very Good 4.0 /5 Latest Reviews Call
Holiday Inn Express Easton - Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.34 miles south of Eastern Chesapeake Shore
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-11:00pm
  • Midscale Downtown property
From$108
Very Good 4.5 /5 Guest Reviews Call
Comfort Inn Easton : 8523 Ocean Gateway 8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Includes a pool: 9:00am-9:00pm Outdoor Pool
  • Inexpensive Rural hotel
From$76
Very Good 4.0 /5 Reviews Call
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
  • Mid-scale Riverfront hotel
From$137
Very Good 4.5 /5 Latest Reviews Call
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 ~12.17 miles west of Eastern Chesapeake Shore
  • Pool available: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Two star Resort hotel
From$80
Average 3.5 /5 Hotel Reviews Call
Hampton Inn - Easton 8058 Ocean Gateway, Easton, MD 21601 ~12.29 miles south of Eastern Chesapeake Shore
  • Pool available: Pool Hours 6am to 10pm
  • Cheap Downtown property
From$119
Very Good 4.5 /5 Hotel Reviews Call
Harbourtowne Golf Resort & Conference Center 9784 Martingham Dr., Saint Michaels, MD 21663 ~14.45 miles southwest of Eastern Chesapeake Shore
  • Pool details: May - September Olympic Size Outdoor Pool with Lifeguard
  • 3 star Riverfront property
From$99
Average 3.5 /5 Guest Reviews Call
St. Michaels Inn 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Affordable Resort property
From$69
Average 3.5 /5 Reviews Call
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
  • Includes a pool
  • 4 star Resort hotel
From$245
Very Good 4.5 /5 Read Reviews Call
Holiday Inn Express & Suites Chestertown Md 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool details: Indoor heated pool. Open 8am-10pm
  • Affordable Suburban hotel
From$115
Very Good 4.0 /5 Guest Reviews Call
Knapp's Narrows Marina & Inn - Tilghman Island 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~22.95 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Luxury 5 star Oceanfront property
Harrison's Chesapeake House - Tilghman 21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.18 miles southwest of Eastern Chesapeake Shore
  • Has swimming pool
  • Cheap Riverfront hotel
Holiday Inn Express & Suites 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
  • Midscale hotel
From$69
Very Good 4.5 /5 Review Score Call
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
  • High-end Downtown hotel
From$119
Very Good 4.0 /5 Hotel Reviews Call
Hyatt Regency Chesapeake Bay : 100 Heron Blvd.
+1-800-230-4134
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Pool in hotel
  • 4 star property
From$219
Very Good 4.0 /5 Recent Reviews Call
Holiday Inn Express Cambridge Md in Cambridge 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • With a pool!
  • 3-star Rural hotel
From$80
Very Good 4.0 /5 Read Reviews Call
Crowne Plaza : 173 Jennifer Rd. 173 Jennifer Rd., Annapolis, MD 21401 ~28.29 miles west of Eastern Chesapeake Shore
  • Pool details: 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.
  • High-end Suburban property
From$109
Average 3.5 /5 Review Score 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.
  • Three Star Suburban hotel
From$89
Very Good 4.0 /5 Read Reviews Call
Best Western - Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~28.53 miles west of Eastern Chesapeake Shore
  • Includes a pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Affordable Suburban property
From$62
Average 3.5 /5 Recent Reviews Call
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 Whirlpool Weekdays: 5pm-10pm Fridays: 3pm - 10pm Weekends: 10am - 10pm Summer: 10am - 10pm daily
  • Affordable Suburban property
From$79
Very Good 4.5 /5 Review Score Call
Annapolis Courtyard by Marriott 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • With a pool!
  • 3 star Downtown hotel
From$79
Very Good 4.0 /5 Guest Reviews Call
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.
  • Mid-scale hotel
From$89
Very Good 4.0 /5 Guest Reviews Call
Country Inn & Suites in Annapolis 2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • We have a pool
  • Midscale Suburban hotel
From$75
Very Good 4.0 /5 Hotel Reviews Call
Hampton Inn 22871 Sussex Highway, Seaford, DE 19973 ~29.59 miles southeast of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Midscale Rural property
From$107
Very Good 4.5 /5 Reviews Call
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