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
From$74
Very Good 4.0 /5 Reviews Call BookMore Details
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
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
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
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
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
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
From$54
Average 3.0 /5 Latest Reviews Call BookMore Details
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
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
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
From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
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
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
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
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
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
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
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
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
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
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
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
From$56
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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
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
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
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
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
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
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
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
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
From$69
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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
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
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
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
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
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
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
From$80
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