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Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Best Western Plus Easton Inn in Easton +1-800-230-4134 8708 Alicia Dr., Easton, MD 21601 ~11.09 miles south of Eastern Chesapeake Shore
  • Pool in hotel: Indoor swimming pool & hot tub
  • Affordable hotel
From$92
Excellent 5.0 /5Guest Reviews
Hilton Garden Inn Kent Island +1-800-997-5148 3206 Main St., Grasonville, MD 21638 ~12.03 miles west of Eastern Chesapeake Shore
  • Pool available: Indoor pool open daily 6 AM-10PM
  • 3-star Riverfront property
From$164
Very Good 4.5 /5Recent Reviews
Best Western Kent Narrows Inn +1-888-205-8144 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.
  • 2 star Resort property
From$75
Average 3.5 /5Recent Reviews
Hampton Inn +1-800-997-5149 8058 Ocean Gateway, Easton, MD 21601 ~12.29 miles south of Eastern Chesapeake Shore
  • Includes a pool
  • Cheap Downtown property
From$184
Very Good 4.5 /5Read Reviews
Harbourtowne Golf Resort - Saint Michaels +1-800-230-4134 9784 Martingham Dr., Saint Michaels, MD 21663 ~14.45 miles southwest of Eastern Chesapeake Shore
  • Pool details: Memorial day to Labor day.Outdoor
  • 3-star Riverfront hotel
From$119
Average 3.5 /5Guest Reviews
St. Michaels Inn : 1228 South Talbot St. +1-800-997-5148 1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Affordable Resort hotel
From$76
Average 3.0 /5Recent Reviews
The Inn at Perry Cabin - St. Michael's +1-888-205-8144 308 Watkins Lane, St. Michael's, MD 21663 ~15.81 miles southwest of Eastern Chesapeake Shore
  • With a pool!
  • High end Resort hotel
From$245
Very Good 4.5 /5Review Score
Holiday Inn Express & Suites - Chestertown +1-800-997-5149 150 Scheeler Rd., Chestertown, MD 21620 ~19.78 miles north of Eastern Chesapeake Shore
  • Includes a pool: Indoor heated pool. Open 8am-10pm
  • Midscale Suburban hotel
From$87
Very Good 4.0 /5Read Reviews
Baymont Inn & Suites +1-800-230-4134 1259 Corn Crib Rd., Harrington, DE 19952 ~24.33 miles east of Eastern Chesapeake Shore
  • Has a pool!
  • 3 star Rural property
From$45
Average 3.5 /5Hotel Reviews
Holiday Inn Express & Suites +1-800-997-5148 17271 South Dupont Highway, Harrington, DE 19952 ~24.35 miles east of Eastern Chesapeake Shore
  • Pool available: We have an outdoor pool the hrs are 9a-9p
  • Three Star hotel
From$65
Very Good 4.5 /5Review Score
The Westin Annapolis in Annapolis +1-888-205-8144 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 property
From$109
Very Good 4.0 /5Recent Reviews
Hyatt Regency Chesapeake Bay : 100 Heron Blvd. +1-800-997-5149 100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • With a pool!
  • 4 star hotel
From$179
Very Good 4.0 /5Recent Reviews
Holiday Inn Express Cambridge Md in Cambridge +1-800-230-4134 2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Has swimming pool
  • Mid-scale Rural hotel
From$119
Very Good 4.0 /5Guest Reviews
Doubletree Hotel Annapolis - Annapolis +1-800-997-5148 210 Holiday Court, Annapolis, MD 21401 ~28.44 miles west of Eastern Chesapeake Shore
  • Has swimming pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Three Star Suburban property
From$109
Very Good 4.0 /5Latest Reviews
Best Western Annapolis in Annapolis +1-888-205-8144 2520 Riva Rd., Annapolis, MD 21401 ~28.51 miles west of Eastern Chesapeake Shore
  • With a pool!
  • 2 star Suburban hotel
From$55
Average 3.5 /5Guest Reviews
Hampton Inn & Suites Annapolis : 124 Womack Dr. +1-800-997-5149 124 Womack Dr., Annapolis, MD 21401 ~28.52 miles west of Eastern Chesapeake Shore
  • Includes a pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Midscale Suburban hotel
From$88
Very Good 4.0 /5Guest Reviews
Springhill Suites by Marriott Annapolis in Annapolis +1-800-230-4134 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~28.62 miles west of Eastern Chesapeake Shore
  • Pool details: Indoor Swimming Pool with WhirlpoolWeekdays: 5pm-10pmFridays: 3pm - 10pmWeekends: 10am - 10pm
  • Affordable Suburban property
From$79
Very Good 4.5 /5Latest Reviews
Hilton Garden Inn Annapolis in Annapolis +1-800-997-5148 305 Harry South Truman, Annapolis, MD 21401 ~28.89 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.
  • 3-star property
From$89
Very Good 4.0 /5Hotel Reviews
Country Inn & Suites +1-888-205-8144 2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • Pool in hotel
  • 3-star Suburban property
From$70
Very Good 4.0 /5Read Reviews
Hampton Inn in Seaford +1-800-997-5149 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 /5Reviews
Hilton Garden Inn Dover in Dover +1-800-230-4134 1706 North Dupont Highway, Dover, DE 19901 ~30.33 miles northeast of Eastern Chesapeake Shore
  • With a pool!
  • Mid-scale Suburban property
From$89
Very Good 4.5 /5Read Reviews
Comfort Suites +1-800-997-5148 23420 Sussex Highway, Seaford, DE 19973 ~30.36 miles southeast of Eastern Chesapeake Shore
  • We have a pool
  • 2 star Highway property
From$69
Average 3.5 /5Hotel Reviews
Hampton Inn Dover : 1568 North Dupont Highway +1-888-205-8144 1568 North Dupont Highway, Dover, DE 19901 ~30.49 miles northeast of Eastern Chesapeake Shore
  • Pool in hotel
  • Two star Suburban property
From$50
Very Good 4.0 /5Latest Reviews
Best Western Galaxy Inn - Dover +1-800-997-5149 1700 East Lebanon Rd., Dover, DE 19901 ~30.82 miles east of Eastern Chesapeake Shore
  • Pool available: Seasonal outdoor pool. Open from May through September. 10am to 10pm.
  • Three Star Suburban hotel
From$60
Average 3.5 /5Guest Reviews
Holiday Inn Dover Downtown +1-800-230-4134 561 North Dupont Highway, Dover, DE 19901 ~31.00 miles northeast of Eastern Chesapeake Shore
  • Pool available: We have an outdoor seasonal pool. Open daily 9.00am to 8.00pm during the Summer season.
  • Affordable Downtown property
From$69
Average 3.5 /5Guest Reviews
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