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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 hotel
From$107
Excellent 5.0 /5 Reviews Call
Best Western Denton Inn - Denton 521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • We have a pool ready for use
  • Three Star Highway property
From$70
Very Good 4.0 /5 Review Score Call
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601 ~11.34 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor Pool & Whirlpool 9:00am-11:00pm
  • Three Star Downtown property
From$93
Very Good 4.5 /5 Reviews Call
Comfort Inn Easton 8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Pool available: 9:00am-9:00pm Outdoor Pool
  • Two star Rural hotel
From$75
Very Good 4.0 /5 Reviews Call
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
  • Affordable Riverfront property
From$137
Very Good 4.5 /5 Read 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 property
From$80
Average 3.5 /5 Hotel Reviews Call
Hampton Inn 8058 Ocean Gateway, Easton, MD 21601 ~12.29 miles south of Eastern Chesapeake Shore
  • Pool in hotel
  • Two-star Downtown property
From$129
Very Good 4.5 /5 Read Reviews Call
Harbourtowne Golf Resort & Conference Center in Saint Michaels 9784 Martingham Dr., Saint Michaels, MD 21663 ~14.45 miles southwest of Eastern Chesapeake Shore
  • Has swimming pool: May - September Olympic Size Outdoor Pool with Lifeguard
  • 3 star Riverfront property
From$99
Average 3.5 /5 Recent Reviews Call
St. Michaels Harbour Inn Marina & Spa - St. Michaels 101 North Harbor Rd., St. Michaels, MD 21663 ~15.44 miles southwest of Eastern Chesapeake Shore
  • We have a pool
  • Three Star Resort hotel
St. Michaels Inn : 1228 South Talbot St. 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Three Star Resort hotel
From$69
Average 3.0 /5 Reviews Call
The Inn at Perry Cabin
+1-888-690-5247
308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • Includes a pool
  • Four star Resort hotel
From$245
Very Good 4.5 /5 Hotel Reviews Call
Holiday Inn Express & Suites Chestertown Md in Chestertown 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Pool in hotel: Indoor heated pool. Open 8am-10pm
  • Mid-scale Suburban property
From$115
Very Good 4.0 /5 Hotel Reviews Call
Knapp's Narrows Marina & Inn in Tilghman Island 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~22.95 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Luxury Five Star Oceanfront property
Holiday Inn Express & Suites in Harrington 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 property
From$69
Very Good 4.5 /5 Guest Reviews Call
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
  • Four-star Downtown property
From$109
Very Good 4.0 /5 Hotel Reviews Call
Hyatt Regency Chesapeake Bay
+1-800-230-4134
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Includes a swimming pool
  • 4 star hotel
From$225
Very Good 4.0 /5 Review Score Call
Holiday Inn Express Cambridge Md 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Has a pool!
  • 3-star Rural hotel
From$80
Very Good 4.0 /5 Read Reviews Call
Crowne Plaza - Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~28.29 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.
  • Expensive Suburban hotel
From$139
Average 3.5 /5 Latest Reviews Call
Doubletree Hotel Annapolis 210 Holiday Court, Annapolis, MD 21401 ~28.44 miles west of Eastern Chesapeake Shore
  • Pool available: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • 3-star Suburban property
From$102
Very Good 4.0 /5 Hotel Reviews Call
Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~28.51 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Economical Suburban property
From$59
Average 3.5 /5 Latest Reviews Call
Hampton Inn & Suites Annapolis : 124 Womack Dr. 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Midscale Suburban property
From$89
Very Good 4.0 /5 Hotel Reviews Call
Springhill Suites by Marriott Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.62 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
  • Mid-scale Suburban property
From$79
Very Good 4.5 /5 Review Score Call
Annapolis Courtyard by Marriott : 2559 Riva Rd. 2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Includes a pool
  • Mid-scale Downtown hotel
From$79
Very Good 4.0 /5 Guest Reviews Call
Hilton Garden Inn Annapolis : 305 Harry South Truman 305 Harry South Truman, Annapolis, MD 21401 ~28.89 miles west of Eastern Chesapeake Shore
  • Pool in hotel: We have an outdoor pool. We open it on Memorial Day and close it on Labor Day.
  • Midscale 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
  • Has swimming pool
  • Three Star Suburban property
From$75
Very Good 4.0 /5 Review Score Call
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