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Chesapeake Beach Hotels with Outdoor or Indoor Pools

Chesapeake Beach Resort & Spa : 4165 Mears Ave. 4165 Mears Ave., Chesapeake Beach, MD 20732
  • We have a pool ready for use
  • Three Star Beach property
From$130
Very Good 4.0 /5Latest Reviews Call
The Inn at Herrington Harbour in Rose Haven 7161 Lake Shore Dr., Rose Haven, MD 20714 ~3.89 miles north of Chesapeake Beach
  • Our hotel comes with a pool
  • High end Beach hotel
Holiday Inn Express : 355 Merrimac Court
+1-800-997-5148
355 Merrimac Court, Prince Frederick, MD 20678 ~9.65 miles south of Chesapeake Beach
  • Includes a pool: Indoor PoolHolds 10,000 gallonsHours are 5am to 9pm
  • Midscale hotel
Harrison's Chesapeake House - Tilghman 21551 Chesapeake House Dr., Tilghman, MD 21671 ~11.10 miles east of Chesapeake Beach
  • Includes a pool
  • Low-priced Riverfront property
Knapp's Narrows Marina & Inn in Tilghman Island 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~11.56 miles east of Chesapeake Beach
  • Has swimming pool
  • Luxury 5 star Oceanfront property
The Inn at Perry Cabin
+1-800-881-1523
308 Watkins Lane, St. Michael's, MD 21663 ~18.50 miles east of Chesapeake Beach
  • Includes a pool
  • Four-star Resort property
From$245
Very Good 4.5 /5Reviews Call
St. Michaels Inn : 1228 South Talbot St. 1228 South Talbot St., St. Michaels, MD 21663 ~18.76 miles east of Chesapeake Beach
  • Our hotel comes with a pool
  • Mid-scale Resort property
Colony South Hotel & Conference Center : 7401 Surratts Rd. 7401 Surratts Rd., Clinton, MD 20735 ~19.20 miles west of Chesapeake Beach
  • With a pool!
  • 3 star Suburban hotel
Harbourtowne Golf Resort & Conference Center 9784 Martingham Dr., Saint Michaels, MD 21663 ~19.37 miles northeast of Chesapeake Beach
  • Has swimming pool: May - SeptemberOlympic Size Outdoor Pool with Lifeguard
  • Mid-scale Riverfront hotel
From$99
Average 3.5 /5Reviews Call
Comfort Suites 11765 Business Park Dr., Waldorf, MD 20601 ~19.60 miles west of Chesapeake Beach
  • Our hotel comes with a pool
  • Affordable Suburban hotel
From$109
Average 3.5 /5Reviews Call
Towneplace Suites by Marriott Jba - Clinton 7800 Ferry Ave., Clinton, MD 20735 ~20.30 miles west of Chesapeake Beach
  • Pool details: Heated Indoor Pool and Hot Tub
  • Midscale Suburban property
From$99
Very Good 4.5 /5Reviews Call
Courtyard by Marriott Waldorf in Waldorf 3145 Crain Highway, Waldorf, MD 20603 ~20.48 miles west of Chesapeake Beach
  • Pool available: Indoor Swimming Pool and Whirlpool. Hours of operation are 6:00 am to 10:00 pm
  • Midscale Suburban hotel
Springhill Suites by Marriott Annapolis : 189 Admiral Cochrane Dr. 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~20.96 miles north of Chesapeake Beach
  • Pool available: Indoor Swimming Pool with WhirlpoolWeekdays: 5pm-10pmFridays: 3pm - 10pmWeekends: 10am - 10pmSummer: 10am - 10pm daily
  • Mid-scale Suburban property
From$79
Very Good 4.5 /5Review Score Call
Hilton Garden Inn Annapolis 305 Harry South Truman, Annapolis, MD 21401 ~21.11 miles north of Chesapeake Beach
  • Pool details: 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 /5Reviews Call
Hampton Inn & Suites Annapolis : 124 Womack Dr. 124 Womack Dr., Annapolis, MD 21401 ~21.12 miles north of Chesapeake Beach
  • Pool available: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Affordable Suburban property
Annapolis Courtyard by Marriott - Annapolis 2559 Riva Rd., Annapolis, MD 21401 ~21.22 miles north of Chesapeake Beach
  • Includes a swimming pool
  • Affordable Downtown hotel
From$79
Very Good 4.0 /5Review Score Call
The Westin Annapolis : 100 Westgate Cir 100 Westgate Cir, Annapolis, MD 21401 ~21.27 miles north of Chesapeake Beach
  • Has swimming pool: indoor pool. lifeguard on duty. hours vary based upon season
  • Four-star Downtown hotel
From$130
Very Good 4.0 /5Latest Reviews Call
Best Western 2520 Riva Rd., Annapolis, MD 21401 ~21.52 miles north of Chesapeake Beach
  • Pool available: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Mid-scale Suburban hotel
Crowne Plaza in Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~21.83 miles north of Chesapeake Beach
  • Has swimming 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.
  • Four star Suburban property
Country Inn & Suites 2600 Housley Rd., Annapolis, MD 21401 ~21.88 miles north of Chesapeake Beach
  • Has swimming pool
  • 3 star Suburban hotel
From$75
Very Good 4.0 /5Reviews Call
Hampton Inn Bowie - Bowie 15202 Major Lansdale Blvd., Bowie, MD 20716 ~22.18 miles northwest of Chesapeake Beach
  • Includes a pool
  • Three Star Downtown property
From$124
Very Good 4.0 /5Latest Reviews Call
Hilton Garden Inn Solomons - Dowell 13100 Dowell Rd., Dowell, MD 20688 ~22.56 miles south of Chesapeake Beach
  • We have a pool ready for use
  • 3 star Riverfront hotel
From$103
Very Good 4.5 /5Recent Reviews Call
Best Western Plus DC Hotel Largo Fedex Field 9421 Largo Dr. West, Largo, MD 20774 ~22.57 miles northwest of Chesapeake Beach
  • Pool available: Indoor 12Ft long pool; M-F 5pm-9pm; Sat-Sun 11pm-9pm.
  • Three Star Suburban hotel
Fairbridge Inn & Suites in Capital Heights 8850 Hampton Mall Dr. North, Capital Heights, MD 20743 ~22.73 miles northwest of Chesapeake Beach
  • Includes a pool
  • Low Cost Suburban property
La Quinta Inn & Suites in Capitol Heights 55 Hampton Park Blvd., Capitol Heights, MD 20743 ~22.74 miles northwest of Chesapeake Beach
  • Pool details: Outdoor
  • Cheap Suburban hotel
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