Chestertown Hotels with Pools - Outdoor/Indoor Pools in Chestertown MD

Chestertown 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 Chestertown, MD for your upcoming individual or family vacation. We list the best pool equipped, kid friendly Chestertown Maryland hotel and motel rooms for children. Review the list of Chestertown hotels with indoor or outdoor pools below to find the perfect lodging for you and your kids.
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Chestertown Hotels with Outdoor or Indoor Pools

Quality Inn - Grasonville 101 Vfw Ave., Grasonville, MD 21638 Call ~18.54 miles southwest of Chestertown
  • Has a pool!
  • Low Cost Resort property
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From$74
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Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 Call ~19.04 miles southwest of Chestertown
  • Has swimming pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Three Star Resort hotel
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From$80
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Hilton Garden Inn Kent Island Marina : 3206 Main St. 3206 Main St., Grasonville, MD 21638 Call ~19.08 miles southwest of Chestertown
  • Pool details: Indoor pool open daily 5 AM-11PM
  • Mid-scale Riverfront hotel
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From$121
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Holiday Inn Belcamp Aberdeen Area An Ihg Hotel - Belcamp 1326 Policy Dr., Belcamp, MD 21017 Call ~20.96 miles northwest of Chestertown
  • Pool details: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Mid-scale Suburban hotel
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From$80
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Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area 1807 Edgewood Rd., Edgewood, MD 21040 Call ~21.05 miles northwest of Chestertown
  • We have a pool
  • Three Star Suburban property
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From$54
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Towneplace Suites Edgewood Aberdeen 1357 Belcamp Rd., Belcamp, MD 21017 Call ~21.21 miles northwest of Chestertown
  • Includes a pool: Our indoor heated pool is open from 7 am to 10 pm.
  • Affordable Rural hotel
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From$89
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Hampton Inn & Suites Edgewood/Aberdeen-South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 Call ~21.33 miles northwest of Chestertown
  • Includes a pool: Indoor Pool available 6AM to 10PM
  • Affordable Suburban hotel
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From$95
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Kent Island Resort in Stevensville 500 Kent Manor Dr., Stevensville, MD 21666 Call ~21.50 miles southwest of Chestertown
  • Includes a pool: Outdoor (seasonal pool)
  • 4 star Riverfront property
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From$125
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Hilton Garden Inn Aberdeen - Aberdeen 1050 Beards Hill Rd., Aberdeen, MD 21001 Call ~22.48 miles north of Chestertown
  • Pool details: FREE INDOOR W/ HOT TUB
  • Three Star Suburban hotel
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From$110
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Holiday Inn Express Aberdeen by IHG : 1007 Beards Hill Rd. 1007 Beards Hill Rd., Aberdeen, MD 21001 Call ~22.51 miles north of Chestertown
  • Pool available: Enjoy a relaxing dip in our indoor-heated salt water pool. The pool is located on the first floor and has direct access to our outdoor patio area. Pool is open daily from 8am-10pm.
  • Mid-scale Highway property
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From$147
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Hampton Inn & Suites Baltimore / Aberdeen 795 West Bel Air Ave., Aberdeen, MD 21001 Call ~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • Economical Highway property
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From$89
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Comfort Inn & Suites Aberdeen Near Apg in Aberdeen 980 Hospitality Way, Aberdeen, MD 21001 Call ~22.75 miles north of Chestertown
  • Pool details: Seasonal Large Outdoor Pool with picnic tables and grills
  • 3 star Highway property
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From$84
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Fairfield Inn N Stes Marriott - Aberdeen 907 Barnett Lane, Aberdeen, MD 21001 Call ~22.77 miles north of Chestertown
  • Includes a swimming pool
  • Mid-scale property
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From$90
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Hilton Garden Inn Baltimore/White Marsh in Baltimore 5015 Campbell Blvd., Baltimore, MD 21236 Call ~23.76 miles west of Chestertown
  • Includes a pool: Indoor Pool
  • Mid-scale Suburban hotel
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From$89
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Hampton Inn Baltimore/White Marsh 8225 Town Center Dr., Nottingham, MD 21236 Call ~23.79 miles west of Chestertown
  • Has swimming pool: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • 3 star Suburban property
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From$89
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Country Inn & Suites by Radisson Baltimore North Md - Rosedale 8825 Yellow Brick Rd., Rosedale, MD 21237 Call ~23.90 miles west of Chestertown
  • Pool available: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Midscale Suburban hotel
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From$80
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Fairfield Inn & Suites by Marriott White Marsh in Baltimore 8477 Cordon Way, Baltimore, MD 21236 Call ~23.93 miles west of Chestertown
  • Pool available: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • Mid-scale Suburban hotel
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From$89
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Best Western Denton Inn in Denton 521 Fleetwood Rd., Denton, MD 21629 Call ~25.35 miles southeast of Chestertown
  • Includes a pool
  • Three Star Highway hotel
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From$68
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Best Western Plus Hotel & Conference Center : 5625 O'donnell St. 5625 O'donnell St., Baltimore, MD 21224 Call ~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Mid-scale Highway property
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From$72
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Hilton Garden Inn Dover : 1706 North Dupont Highway 1706 North Dupont Highway, Dover, DE 19901 Call ~27.40 miles east of Chestertown
  • Has swimming pool: Pool open daily form 8am-10pm.
  • Mid-scale Suburban property
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From$84
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The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 Call ~28.40 miles southwest of Chestertown
  • Pool in hotel: indoor pool. hours vary based upon season
  • High end Downtown hotel
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From$139
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Comfort Inn & Suites : 764 Dover Leipsic Rd. 764 Dover Leipsic Rd., Dover, DE 19901 Call ~28.78 miles east of Chestertown
  • We have a pool ready for use
  • Three Star Suburban property
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From$83
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Hyatt Place Baltimore Inner Harbor in Baltimore 511 South Central Ave., Baltimore, MD 21202 Call ~28.89 miles west of Chestertown
  • Pool in hotel: INDOOR POOL
  • Affordable Downtown hotel
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From$85
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Hilton Garden Inn Baltimore Inner Harbor 625b South President St., Baltimore, MD 21202 Call ~29.09 miles west of Chestertown
  • Includes a pool
  • 3 star Downtown hotel
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From$110
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Homewood Suites by Hilton Baltimore 625a South President St., Baltimore, MD 21202 Call ~29.09 miles west of Chestertown
  • Pool in hotel
  • Midscale Downtown property
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From$80
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Residence Inn Dover in Dover 600 Jefferic Blvd., Dover, DE 19901 Call ~29.10 miles east of Chestertown
  • Includes a swimming pool
  • Four star Suburban hotel
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From$125
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Wyndham Garden Dover Downtown - Dover 561 North Dupont Highway, Dover, DE 19901 Call ~29.11 miles east of Chestertown
  • Pool details: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • Three Star Downtown hotel
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From$71
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Roost Baltimore 2460 Terrapin Way, Baltimore, MD 21215 Call ~29.19 miles west of Chestertown
  • Pool details: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • 4-star hotel
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From$129
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La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie - Glen Burnie 6323 Ritchie Highway, Glen Burnie, MD 21061 Call ~29.21 miles west of Chestertown
  • Has swimming pool: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • Affordable Suburban property
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From$75
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Red Roof Inn Baltimore South - Glen Burnie in Glen Burnie 6600 Ritchie Highway, Glen Burnie, MD 21061 Call ~29.23 miles west of Chestertown
  • Pool in hotel: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Low Cost Airport property
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From$57
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Holiday Inn Express Easton in Easton 8561 Ocean Gateway, Easton, MD 21601 Call ~29.32 miles south of Chestertown
  • Pool in hotel: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3-star Rural hotel
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From$115
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Quality Inn : 8523 Ocean Gateway 8523 Ocean Gateway, Easton, MD 21601 Call ~29.37 miles south of Chestertown
  • Includes a pool: 9:00am-9:00pm Outdoor Pool
  • Economy Rural property
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From$79
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Comfort Inn & Suites 1 Center Dr., North East, MD 21901 Call ~29.39 miles north of Chestertown
  • Pool details: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • Three Star Rural property
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From$67
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Comfort Inn 8801 Loch Raven Blvd., Towson, MD 21286 Call ~29.62 miles west of Chestertown
  • Pool available: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Economy Suburban hotel
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From$56
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The Royal Sonesta Harbor Court Baltimore : 550 Light St. 550 Light St., Baltimore, MD 21202 Call ~29.64 miles west of Chestertown
  • Pool details: Mon-Sun: 5am-10pm Indoor pool Length: 11.25 meters Width: 7 meters 5 feet deep throughout Swimming pool is maintained at 88 degrees Hot tub is maintained at 104 degrees
  • 4-star Downtown hotel
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From$79
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Hampton Inn & Suites Baltimore Inner Harbor in Baltimore 131 East Redwood St., Baltimore, MD 21202 Call ~29.67 miles west of Chestertown
  • Includes a pool: Indoor pool. Pool hours from Labor Day to Memorial Day are Monday thru Friday 4:00PM to 9:00PM & Saturday to Sunday 10:00AM to 9:00PM. Pool hours from Memorial Day to Labor Day are Monday thru Thursday 4:00PM to 9:00PM & Friday thru Sunday, 10:00AM to 9:00PM.
  • Midscale Downtown hotel
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From$89
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The Royal Sonesta Harbor Court - Baltimore 550 Light St., Baltimore, MD 21230 Call ~29.68 miles west of Chestertown
  • Pool in hotel: Our rooftop indoor pool is open 5am-10pm daily
  • 4 star Downtown property
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From$125
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Hyatt Regency Baltimore Inner Harbor 300 Light St., Baltimore, MD 21202 Call ~29.71 miles west of Chestertown
  • With a pool!
  • 4 star Convention Center hotel
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From$125
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Crowne Plaza Annapolis An Ihg Hotel in Annapolis 173 Jennifer Rd., Annapolis, MD 21401 Call ~29.76 miles southwest of Chestertown
  • Pool details: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Hours vary.
  • 3 star Suburban hotel
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From$80
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Home2 Suites by Hilton Dover De 222 South Dupont Highway, Dover, DE 19901 Call ~29.76 miles east of Chestertown
  • Has swimming pool: 6am - 10pm
  • Low Cost Downtown hotel
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From$99
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Hampton Inn & Suites - Annapolis Hampton Inn 124, Annapolis, MD 21401 Call ~29.81 miles southwest of Chestertown
  • Has swimming pool: Seasonal outdoor pool
  • 3 star Highway property
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From$80
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Days Inn by Wyndham Baltimore Inner Harbor 100 Hopkins Pl, Baltimore, MD 21201 Call ~29.93 miles west of Chestertown
  • Includes a pool: Outdoor pool (seasonal)
  • Affordable Downtown hotel
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From$73
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Holiday Inn Express Towson Baltimore North An Ihg Hotel - Towson 1100 Cromwell Bridge Rd., Towson, MD 21286 Call ~30.06 miles west of Chestertown
  • Pool in hotel: Our outdoor pool is open Memorial day to Labor day 10am-8pm. Life guard is always on duty. The pool is maximum 6 ft deep and has handicap lift.
  • 3 star Suburban property
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From$69
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Doubletree by Hilton Hotel Annapolis - Annapolis 210 Holiday Court, Annapolis, MD 21401 Call ~30.10 miles southwest of Chestertown
  • Has swimming pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • 3 star Suburban property
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From$149
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Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401 Call ~30.17 miles southwest of Chestertown
  • Has swimming pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Two-star Suburban hotel
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From$84
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Wingate by Wyndham North East in North East 39 Elwoods Rd., North East, MD 21901 Call ~30.29 miles north of Chestertown
  • Pool in hotel: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • 3-star Rural hotel
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From$71
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Hampton Inn & Suites Annapolis - Annapolis 124 Womack Dr., Annapolis, MD 21401 Call ~30.39 miles southwest of Chestertown
  • Pool in hotel: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3 star Suburban property
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From$70
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Sonesta Es Suites Annapolis - Annapolis 170 Admiral Cochrane Dr., Annapolis, MD 21401 Call ~30.57 miles southwest of Chestertown
  • Has swimming pool: Seasonal Outdoor Pool
  • Affordable Suburban property
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From$99
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Best Western Galaxy Inn - Dover 1700 East Lebanon Rd., Dover, DE 19901 Call ~31.11 miles east of Chestertown
  • Includes a pool: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Mid-scale Suburban hotel
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From$70
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Hampton / Home2 Suites Towson : 21 West Susquehanna Ave. 21 West Susquehanna Ave., Towson, MD 21204 Call ~31.53 miles west of Chestertown
  • Pool in hotel: Indoor Pool 9 AM - 10 PM
  • Three Star Downtown hotel
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From$80
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