Eastern Chesapeake Shore Hotels with Pools - Outdoor/Indoor Pools in Eastern Chesapeake Shore MD

Eastern Chesapeake Shore hotels and motels with swimming pools that are perfect for a family are listed below. Search for cheap and discount hotel rates at hotels with a pool in or near Eastern Chesapeake Shore, MD for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Eastern Chesapeake Shore Maryland hotel and motel rooms for children. Review the list of Eastern Chesapeake Shore hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.

Star Rating
Hotel Name
Price Range (USD)to
Amenities

Eastern Chesapeake Shore Hotels with Outdoor or Indoor Pools

Best Western Plus Easton Inn
+1-888-690-5281

How should we direct your call?

New Reservations: +1-888-690-5281 Group Sales: +1-888-494-8863 Front Desk: 14108227100
8708 Alicia Dr., Easton, MD 21601 ~11.09 miles south of Eastern Chesapeake Shore
  • Pool available: Indoor swimming pool & hot tub
  • 3 star property
More PhotosPool image of Best Western Plus Easton Inn
From$107
Excellent 5.0 /5Latest Reviews Call
Best Western Denton Inn - Denton
+1-800-230-4134

How should we direct your call?

New Reservations: +1-800-230-4134 Group Sales: +1-888-494-8863 Front Desk: 14104798400
521 Fleetwood Rd., Denton, MD 21629 ~11.11 miles east of Eastern Chesapeake Shore
  • Has swimming pool
  • 3 star Highway hotel
More Photos Pool image of Best Western Denton Inn
From$70
Very Good 4.0 /5Reviews Call
Holiday Inn Express Easton : 8561 Ocean Gateway
+1-800-997-5148

How should we direct your call?

New Reservations: +1-800-997-5148 Group Sales: +1-888-494-8863 Front Desk: 14108196500
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
More Photos Pool image of Holiday Inn Express Easton
From$108
Very Good 4.5 /5Recent Reviews Call
Comfort Inn Easton
+1-888-690-5247

How should we direct your call?

New Reservations: +1-888-690-5247 Group Sales: +1-888-494-8863 Front Desk: 14108208333
8523 Ocean Gateway, Easton, MD 21601 ~11.39 miles south of Eastern Chesapeake Shore
  • Pool available: 9:00am-9:00pmOutdoor Pool
  • Economy Rural hotel
More Photos Pool image of Comfort Inn Easton
From$76
Very Good 4.0 /5Guest Reviews Call
Hilton Garden Inn Kent Island - Grasonville
+1-888-305-3366

How should we direct your call?

New Reservations: +1-888-305-3366 Group Sales: +1-888-494-8863 Front Desk: 14108273877
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
More Photos Photo of Hilton Garden Inn Kent Island Pool
From$137
Very Good 4.5 /5Reviews Call
Best Western Kent Narrows Inn
+1-800-881-1523

How should we direct your call?

New Reservations: +1-800-881-1523 Group Sales: +1-888-494-8863 Front Desk: 14108276767
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
More Photos Photo of Best Western Kent Narrows Inn Pool
From$80
Average 3.5 /5Read Reviews Call
Hampton Inn : 8058 Ocean Gateway
+1-800-997-5149

How should we direct your call?

New Reservations: +1-800-997-5149 Group Sales: +1-888-494-8863 Front Desk: 14108222200
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
More Photos Photo of Hampton Inn Pool
From$119
Very Good 4.5 /5Guest Reviews Call
Harbourtowne Golf Resort & Conference Center
+1-888-690-5281

How should we direct your call?

New Reservations: +1-888-690-5281 Group Sales: +1-888-494-8863 Front Desk: 18004469066
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
More Photos Swimming pool at Harbourtowne Golf Resort & Conference Center
From$99
Average 3.5 /5Reviews Call
St. Michaels Inn - St. Michaels
+1-800-230-4134

How should we direct your call?

New Reservations: +1-800-230-4134 Group Sales: +1-888-494-8863 Front Desk: 14107453333
1228 South Talbot St., St. Michaels, MD 21663 ~15.77 miles southwest of Eastern Chesapeake Shore
  • Pool in hotel
  • Three Star Resort hotel
More Photos Pool image of St. Michaels Inn
From$69
Average 3.5 /5Read Reviews Call
The Inn at Perry Cabin
+1-800-997-5148

How should we direct your call?

New Reservations: +1-800-997-5148 Group Sales: +1-888-494-8863
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
More Photos Pool image of The Inn at Perry Cabin
From$245
Very Good 4.5 /5Read Reviews Call
Holiday Inn Express & Suites Chestertown Md : 150 Scheeler Rd.
+1-888-690-5247

How should we direct your call?

New Reservations: +1-888-690-5247 Group Sales: +1-888-494-8863 Front Desk: 14107780778
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
More Photos Photo of Holiday Inn Express & Suites Chestertown Md Pool
From$115
Very Good 4.0 /5Review Score Call
Knapp's Narrows Marina & Inn - Tilghman Island
+1-888-305-3366

How should we direct your call?

New Reservations: +1-888-305-3366 Group Sales: +1-888-494-8863 Front Desk: 14108862720
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
More Photos Photo of Knapp's Narrows Marina & Inn Pool
From$80
Call
Harrison's Chesapeake House : 21551 Chesapeake House Dr.
+1-800-881-1523

How should we direct your call?

New Reservations: +1-800-881-1523 Group Sales: +1-888-494-8863 Front Desk: 14108862121
21551 Chesapeake House Dr., Tilghman, MD 21671 ~24.18 miles southwest of Eastern Chesapeake Shore
  • Has a pool!
  • Low priced Riverfront hotel
More Photoshotel room
From$65
Call
Holiday Inn Express & Suites : 17271 South Dupont Highway
+1-800-997-5149

How should we direct your call?

New Reservations: +1-800-997-5149 Group Sales: +1-888-494-8863 Front Desk: 13023988800
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
More PhotosPool image of Holiday Inn Express & Suites
From$69
Very Good 4.5 /5Hotel Reviews Call
The Westin Annapolis
+1-888-690-5281

How should we direct your call?

New Reservations: +1-888-690-5281 Group Sales: +1-888-494-8863 Front Desk: 14109724300
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
More Photos Photo of The Westin Annapolis Pool
From$130
Very Good 4.0 /5Recent Reviews Call
Hyatt Regency Chesapeake Bay - Cambridge
+1-800-230-4134

How should we direct your call?

New Reservations: +1-800-230-4134 Group Sales: +1-888-494-8863
100 Heron Blvd., Cambridge, MD 21613 ~26.51 miles south of Eastern Chesapeake Shore
  • Has a pool!
  • Expensive hotel
More Photos Photo of Hyatt Regency Chesapeake Bay Pool
From$219
Very Good 4.0 /5Guest Reviews Call
Holiday Inn Express Cambridge Md in Cambridge
+1-800-997-5148

How should we direct your call?

New Reservations: +1-800-997-5148 Group Sales: +1-888-494-8863 Front Desk: 14102219900
2715 Ocean Gateway, Cambridge, MD 21613 ~26.86 miles south of Eastern Chesapeake Shore
  • Includes a pool
  • 3-star Rural hotel
More Photos Swimming pool at Holiday Inn Express Cambridge Md
From$80
Very Good 4.0 /5Guest Reviews Call
Crowne Plaza - Annapolis
+1-888-690-5247

How should we direct your call?

New Reservations: +1-888-690-5247 Group Sales: +1-888-494-8863 Front Desk: 14102663131
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
More Photos Swimming pool at Crowne Plaza
From$109
Average 3.5 /5Reviews Call
Hampton Inn & Suites Annapolis - Annapolis
+1-888-305-3366

How should we direct your call?

New Reservations: +1-888-305-3366 Group Sales: +1-888-494-8863 Front Desk: 14105710200
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
More Photos Photo of Hampton Inn & Suites Annapolis Pool
From$89
Very Good 4.0 /5Latest Reviews Call
Best Western
+1-800-881-1523

How should we direct your call?

New Reservations: +1-800-881-1523 Group Sales: +1-888-494-8863 Front Desk: 14102242800
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
More Photos Pool image of Best Western
From$62
Average 3.5 /5Guest Reviews Call
Springhill Suites by Marriott Annapolis in Annapolis
+1-800-997-5149

How should we direct your call?

New Reservations: +1-800-997-5149 Group Sales: +1-888-494-8863 Front Desk: 14433212500
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
More Photos Pool image of Springhill Suites by Marriott Annapolis
From$79
Very Good 4.5 /5Hotel Reviews Call
Annapolis Courtyard by Marriott in Annapolis
+1-888-690-5281

How should we direct your call?

New Reservations: +1-888-690-5281 Group Sales: +1-888-494-8863 Front Desk: 14102661555
2559 Riva Rd., Annapolis, MD 21401 ~28.74 miles west of Eastern Chesapeake Shore
  • Has a pool!
  • 3 star Downtown hotel
More Photos Swimming pool at Annapolis Courtyard by Marriott
From$79
Very Good 4.0 /5Recent Reviews Call
Hilton Garden Inn Annapolis
+1-800-230-4134

How should we direct your call?

New Reservations: +1-800-230-4134 Group Sales: +1-888-494-8863 Front Desk: 14102669006
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
More Photos Swimming pool at Hilton Garden Inn Annapolis
From$89
Very Good 4.0 /5Recent Reviews Call
Country Inn & Suites
+1-800-997-5148

How should we direct your call?

New Reservations: +1-800-997-5148 Group Sales: +1-888-494-8863 Front Desk: 14105716700
2600 Housley Rd., Annapolis, MD 21401 ~29.04 miles west of Eastern Chesapeake Shore
  • Our hotel comes with a pool
  • Three Star Suburban hotel
More Photos Pool image of Country Inn & Suites
From$75
Very Good 4.0 /5Guest Reviews Call
Hampton Inn : 22871 Sussex Highway
+1-888-690-5247

How should we direct your call?

New Reservations: +1-888-690-5247 Group Sales: +1-888-494-8863 Front Desk: 13026294500
22871 Sussex Highway, Seaford, DE 19973 ~29.59 miles southeast of Eastern Chesapeake Shore
  • With a pool!
  • Affordable Rural property
More Photos Photo of Hampton Inn Pool
From$107
Very Good 4.5 /5Hotel Reviews Call
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