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 in Grasonville 101 Vfw Ave., Grasonville, MD 21638
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~18.54 miles southwest of Chestertown
  • We have a pool
  • Cheap Resort property
More Photos Photo of Quality Inn Pool
From$74
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Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638
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~19.04 miles southwest of Chestertown
  • Has swimming pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Mid-scale Resort hotel
More Photos Photo of Best Western Kent Narrows Inn Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Kent Island Marina in Grasonville 3206 Main St., Grasonville, MD 21638
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~19.08 miles southwest of Chestertown
  • Has swimming pool: Indoor pool open daily 5 AM-11PM
  • Mid-scale Riverfront property
More Photos Photo of Hilton Garden Inn Kent Island Marina Pool
From$121
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel - Belcamp 1326 Policy Dr., Belcamp, MD 21017
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~20.96 miles northwest of Chestertown
  • Pool details: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban property
More Photos Photo of Holiday Inn Belcamp Aberdeen Area An Ihg Hotel Pool
From$80
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Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area 1807 Edgewood Rd., Edgewood, MD 21040
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~21.05 miles northwest of Chestertown
  • Pool in hotel
  • Three Star Suburban property
More Photos Pool image of Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
From$54
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Towneplace Suites Edgewood Aberdeen in Belcamp 1357 Belcamp Rd., Belcamp, MD 21017
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~21.21 miles northwest of Chestertown
  • Pool details: Our indoor heated pool is open from 7 am to 10 pm.
  • 3 star Rural hotel
More Photos Swimming pool at Towneplace Suites Edgewood Aberdeen
From$89
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Hampton Inn & Suites Edgewood/Aberdeen-South - Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040
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~21.33 miles northwest of Chestertown
  • Has swimming pool: Indoor Pool available 6AM to 10PM
  • Three Star Suburban hotel
More Photos Photo of Hampton Inn & Suites Edgewood/Aberdeen-South Pool
From$95
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Kent Island Resort 500 Kent Manor Dr., Stevensville, MD 21666
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~21.50 miles southwest of Chestertown
  • Includes a pool: Outdoor (seasonal pool)
  • High-end Riverfront property
More Photos Swimming pool at Kent Island Resort
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen 1050 Beards Hill Rd., Aberdeen, MD 21001
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~22.48 miles north of Chestertown
  • Pool available: FREE INDOOR W/ HOT TUB
  • 3 star Suburban property
More Photos Pool image of Hilton Garden Inn Aberdeen
From$110
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG - Aberdeen 1007 Beards Hill Rd., Aberdeen, MD 21001
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~22.51 miles north of Chestertown
  • Pool details: 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 hotel
More Photos Pool image of Holiday Inn Express Aberdeen by IHG
From$147
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Hampton Inn & Suites Baltimore / Aberdeen - Aberdeen 795 West Bel Air Ave., Aberdeen, MD 21001
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~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • Economical Highway hotel
More Photos Photo of Hampton Inn & Suites Baltimore / Aberdeen Pool
From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg : 980 Hospitality Way 980 Hospitality Way, Aberdeen, MD 21001
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~22.75 miles north of Chestertown
  • Has swimming pool: Seasonal Large Outdoor Pool with picnic tables and grills
  • 3 star Highway hotel
More Photos Pool image of Comfort Inn & Suites Aberdeen Near Apg
From$84
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Fairfield Inn N Stes Marriott 907 Barnett Lane, Aberdeen, MD 21001
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~22.77 miles north of Chestertown
  • Has a pool!
  • 3 star property
More Photos hotel room
From$90
Very Good 4.0 /5 Read Reviews Call BookMore Details
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Hilton Garden Inn Baltimore/White Marsh - Baltimore 5015 Campbell Blvd., Baltimore, MD 21236
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~23.76 miles west of Chestertown
  • Pool in hotel: Indoor Pool
  • 3 star Suburban hotel
More Photos Photo of Hilton Garden Inn Baltimore/White Marsh Pool
From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh : 8225 Town Center Dr. 8225 Town Center Dr., Nottingham, MD 21236
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~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 hotel
More Photos Swimming pool at Hampton Inn Baltimore/White Marsh
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Country Inn & Suites by Radisson, Baltimore North, MD 8825 Yellow Brick Rd., Rosedale, MD 21237
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~23.90 miles west of Chestertown
  • Pool in hotel: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Mid-scale Suburban hotel
More Photos Pool image of Country Inn & Suites by Radisson, Baltimore North, MD
From$80
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Fairfield Inn & Suites by Marriott White Marsh 8477 Cordon Way, Baltimore, MD 21236
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~23.93 miles west of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • 3 star Suburban hotel
More Photos Photo of Fairfield Inn & Suites by Marriott White Marsh Pool
From$89
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Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629
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~25.35 miles southeast of Chestertown
  • Includes a swimming pool
  • Three Star Highway hotel
More Photos Swimming pool at Best Western Denton Inn
From$68
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center 5625 O'donnell St., Baltimore, MD 21224
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~26.13 miles west of Chestertown
  • Has swimming pool: Indoor heated pool Open 10 am - 10 pm, weekly.
  • 3 star Highway hotel
More Photos Photo of Best Western Plus Hotel & Conference Center Pool
From$72
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Hilton Garden Inn Dover 1706 North Dupont Highway, Dover, DE 19901
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~27.40 miles east of Chestertown
  • Has swimming pool: Pool open daily form 8am-10pm.
  • Midscale Suburban hotel
More Photos Pool image of Hilton Garden Inn Dover
From$84
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Bally's Dover Casino Resort - Dover 1131 North Dupont Highway, Dover, DE 19901
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~28.36 miles east of Chestertown
  • Pool in hotel: Open Daily 7:00 AM to 10:00 PM In-door Heated Pool
  • High-end Resort hotel
More Photos Pool image of Bally's Dover Casino Resort
From$99
Very Good 4.5 /5 Review Score Call BookMore Details
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401
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~28.40 miles southwest of Chestertown
  • Pool in hotel: indoor pool. hours vary based upon season
  • High end Downtown property
More Photos Photo of The Westin Annapolis Pool
From$139
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites 764 Dover Leipsic Rd., Dover, DE 19901
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~28.78 miles east of Chestertown
  • Pool in hotel
  • 3-star Suburban property
More Photos Photo of Comfort Inn & Suites Pool
From$83
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Hyatt Place Baltimore Inner Harbor 511 South Central Ave., Baltimore, MD 21202
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~28.89 miles west of Chestertown
  • Pool details: INDOOR POOL
  • Three Star Downtown hotel
More Photos Swimming pool at Hyatt Place Baltimore Inner Harbor
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor - Baltimore 625b South President St., Baltimore, MD 21202
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~29.09 miles west of Chestertown
  • Has swimming pool
  • 3-star Downtown property
More Photos Photo of Hilton Garden Inn Baltimore Inner Harbor Pool
From$110
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore : 625a South President St. 625a South President St., Baltimore, MD 21202
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~29.09 miles west of Chestertown
  • Has a pool!
  • Mid-scale Downtown property
More Photos Swimming pool at Homewood Suites by Hilton Baltimore
From$80
Very Good 4.5 /5 Review Score Call BookMore Details
Residence Inn Dover : 600 Jefferic Blvd. 600 Jefferic Blvd., Dover, DE 19901
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~29.10 miles east of Chestertown
  • Pool in hotel
  • Expensive Suburban hotel
More Photos Photo of Residence Inn Dover Pool
From$125
Average 3.0 /5 Review Score Call BookMore Details
Wyndham Garden Dover Downtown : 561 North Dupont Highway 561 North Dupont Highway, Dover, DE 19901
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~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.
  • 3 star Downtown hotel
More Photos Swimming pool at Wyndham Garden Dover Downtown
From$71
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La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie 6323 Ritchie Highway, Glen Burnie, MD 21061
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~29.21 miles west of Chestertown
  • Includes a pool: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3-star Suburban property
More Photos Photo of La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie Pool
From$75
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Red Roof Inn Baltimore South - Glen Burnie - Glen Burnie 6600 Ritchie Highway, Glen Burnie, MD 21061
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~29.23 miles west of Chestertown
  • Pool details: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Cheap Airport property
More Photos Swimming pool at Red Roof Inn Baltimore South - Glen Burnie
From$57
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Holiday Inn Express Easton in Easton 8561 Ocean Gateway, Easton, MD 21601
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~29.32 miles south of Chestertown
  • Pool details: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Three Star Rural property
More Photos Swimming pool at Holiday Inn Express Easton
From$115
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Quality Inn 8523 Ocean Gateway, Easton, MD 21601
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~29.37 miles south of Chestertown
  • Has swimming pool: 9:00am-9:00pm Outdoor Pool
  • 2 star Rural hotel
More Photos Pool image of Quality Inn
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites in North East 1 Center Dr., North East, MD 21901
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~29.39 miles north of Chestertown
  • Includes a pool: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • 3-star Rural hotel
More Photos Swimming pool at Comfort Inn & Suites
From$67
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Comfort Inn : 8801 Loch Raven Blvd. 8801 Loch Raven Blvd., Towson, MD 21286
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~29.62 miles west of Chestertown
  • Includes a pool: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Inexpensive Suburban hotel
More Photos Pool image of Comfort Inn
From$56
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore in Baltimore 550 Light St., Baltimore, MD 21202
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~29.64 miles west of Chestertown
  • Pool in hotel: 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
  • High end Downtown property
More Photos Swimming pool at The Royal Sonesta Harbor Court Baltimore
From$79
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Hampton Inn & Suites Baltimore Inner Harbor : 131 East Redwood St. 131 East Redwood St., Baltimore, MD 21202
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~29.67 miles west of Chestertown
  • Pool in hotel: 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.
  • Three Star Downtown hotel
More Photos Photo of Hampton Inn & Suites Baltimore Inner Harbor Pool
From$89
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The Royal Sonesta Harbor Court in Baltimore 550 Light St., Baltimore, MD 21230
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~29.68 miles west of Chestertown
  • Pool details: Our rooftop indoor pool is open 5am-10pm daily
  • Expensive Downtown hotel
More Photos Pool image of The Royal Sonesta Harbor Court
From$125
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Hyatt Regency Baltimore Inner Harbor - Baltimore 300 Light St., Baltimore, MD 21202
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~29.71 miles west of Chestertown
  • Includes a swimming pool
  • High end Convention Center property
More Photos Pool image of Hyatt Regency Baltimore Inner Harbor
From$125
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Crowne Plaza Annapolis An Ihg Hotel 173 Jennifer Rd., Annapolis, MD 21401
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~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.
  • Affordable Suburban hotel
More Photos Photo of Crowne Plaza Annapolis An Ihg Hotel Pool
From$80
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Home2 Suites by Hilton Dover De in Dover 222 South Dupont Highway, Dover, DE 19901
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~29.76 miles east of Chestertown
  • Pool available: 6am - 10pm
  • Low priced Downtown hotel
More Photos Pool image of Home2 Suites by Hilton Dover De
From$99
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Hampton Inn & Suites Hampton Inn 124, Annapolis, MD 21401
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~29.81 miles southwest of Chestertown
  • Includes a pool: Seasonal outdoor pool
  • 3 star Highway hotel
More Photos Swimming pool at Hampton Inn & Suites
From$80
Average 3.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor in Baltimore 100 Hopkins Pl, Baltimore, MD 21201
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~29.93 miles west of Chestertown
  • Has swimming pool: Outdoor pool (seasonal)
  • 3 star Downtown hotel
More Photos Swimming pool at Days Inn by Wyndham Baltimore Inner Harbor
From$73
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Holiday Inn Express Towson Baltimore North An Ihg Hotel 1100 Cromwell Bridge Rd., Towson, MD 21286
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~30.06 miles west of Chestertown
  • Includes a pool: 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.
  • Affordable Suburban property
More Photos Pool image of Holiday Inn Express Towson Baltimore North An Ihg Hotel
From$69
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Doubletree by Hilton Hotel Annapolis : 210 Holiday Court 210 Holiday Court, Annapolis, MD 21401
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~30.10 miles southwest of Chestertown
  • Has swimming pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Three Star Suburban hotel
More Photos Pool image of Doubletree by Hilton Hotel Annapolis
From$149
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Best Western Annapolis in Annapolis 2520 Riva Rd., Annapolis, MD 21401
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~30.17 miles southwest of Chestertown
  • Pool in hotel: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Cheap Suburban property
More Photos Photo of Best Western Annapolis Pool
From$84
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Wingate by Wyndham North East 39 Elwoods Rd., North East, MD 21901
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~30.29 miles north of Chestertown
  • Has swimming pool: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • 3-star Rural property
More Photos Photo of Wingate by Wyndham North East Pool
From$71
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Hampton Inn & Suites Annapolis - Annapolis 124 Womack Dr., Annapolis, MD 21401
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~30.39 miles southwest of Chestertown
  • Pool in hotel: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3-star Suburban hotel
More Photos Swimming pool at Hampton Inn & Suites Annapolis
From$70
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Sonesta Es Suites Annapolis : 170 Admiral Cochrane Dr. 170 Admiral Cochrane Dr., Annapolis, MD 21401
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~30.57 miles southwest of Chestertown
  • Has swimming pool: Seasonal Outdoor Pool
  • 3-star Suburban property
More Photos Swimming pool at Sonesta Es Suites Annapolis
From$99
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Best Western Galaxy Inn in Dover 1700 East Lebanon Rd., Dover, DE 19901
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~31.11 miles east of Chestertown
  • Pool details: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Three Star Suburban property
More Photos Pool image of Best Western Galaxy Inn
From$70
Average 3.5 /5 Latest Reviews Call BookMore Details
Hampton / Home2 Suites Towson 21 West Susquehanna Ave., Towson, MD 21204
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~31.53 miles west of Chestertown
  • Pool available: Indoor Pool 9 AM - 10 PM
  • Three Star Downtown property
More Photos Photo of Hampton / Home2 Suites Towson Pool
From$80
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