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 near Kent Island 101 Vfw Ave., Grasonville, MD 21638
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~18.54 miles southwest of Chestertown
  • We have a pool ready for use
  • Cheap Resort hotel
More Photos Swimming pool at Quality Inn Grasonville near Kent Island
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
  • Pool available: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Affordable Resort hotel
More Photos Photo of Best Western Kent Narrows Inn Pool
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel : 1326 Policy Dr. 1326 Policy Dr., Belcamp, MD 21017
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~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban property
More Photos Swimming pool at Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
From$80
Average 3.0 /5 Review Score Call BookMore Details
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
  • Our hotel comes with a pool
  • Three Star Suburban hotel
More Photos Swimming pool at Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
From$54
Average 3.0 /5 Review Score Call BookMore Details
Towneplace Suites Edgewood Aberdeen : 1357 Belcamp Rd. 1357 Belcamp Rd., Belcamp, MD 21017
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~21.21 miles northwest of Chestertown
  • Has swimming pool: Our indoor heated pool is open from 7 am to 10 pm.
  • 3-star Rural hotel
More Photos Pool image of Towneplace Suites Edgewood Aberdeen
From$89
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Country Inn & Suites by Radisson Bel Air / Aberdeen Md 1435 Handlir Dr., Bel Air, MD 21015
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~21.29 miles northwest of Chestertown
  • Has swimming pool: Outdoor Pool, open Memorial Day - Labor Day
  • Mid-scale Rural hotel
More Photos Swimming pool at Country Inn & Suites by Radisson Bel Air / Aberdeen Md
From$79
Very good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South 2110 Emmorton Park Rd., Edgewood, MD 21040
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~21.33 miles northwest of Chestertown
  • Pool in hotel: Indoor Pool available 6AM to 10PM
  • Affordable Suburban property
More Photos Pool image of Hampton Inn & Suites Edgewood/Aberdeen-South
From$95
Very good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Aberdeen : 1050 Beards Hill Rd. 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 hotel
More Photos Pool image of Hilton Garden Inn Aberdeen
From$110
Very good 4.0 /5 Recent 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 in hotel: 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
More Photos Pool image of Holiday Inn Express Aberdeen by IHG
From$147
Very good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen : 795 West Bel Air Ave. 795 West Bel Air Ave., Aberdeen, MD 21001
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~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • Inexpensive Highway property
More Photos Swimming pool at Hampton Inn & Suites Baltimore/Aberdeen
From$89
Very good 4.5 /5 Hotel 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
  • Pool details: Seasonal Large Outdoor Pool with picnic tables and grills
  • Midscale Highway property
More Photos Pool image of Comfort Inn & Suites Aberdeen Near Apg
From$84
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn N Stes Marriott 907 Barnett Lane, Aberdeen, MD 21001
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~22.77 miles north of Chestertown
  • Includes a swimming pool
  • 3 star hotel
More Photos hotel room
From$90
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh 5015 Campbell Blvd., Baltimore, MD 21236
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~23.76 miles west of Chestertown
  • Pool in hotel: Indoor Pool
  • Three Star Suburban property
More Photos Pool image of Hilton Garden Inn Baltimore/White Marsh
From$89
Average 3.0 /5 Read Reviews Call BookMore Details
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Country Inn & Suites by Radisson, Baltimore North, MD : 8825 Yellow Brick Rd. 8825 Yellow Brick Rd., Rosedale, MD 21237
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~23.90 miles west of Chestertown
  • Has swimming pool: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Affordable Suburban hotel
More Photos Photo of Country Inn & Suites by Radisson, Baltimore North, MD Pool
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh in Baltimore 8477 Cordon Way, Baltimore, MD 21236
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~23.93 miles west of Chestertown
  • Pool available: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • Affordable Suburban property
More Photos Pool image of Fairfield Inn & Suites by Marriott White Marsh
From$89
Very good 4.0 /5 Reviews Call BookMore Details
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Hampton Inn Middletown 117 Sandhill Dr., Middletown, DE 19709
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~24.53 miles northeast of Chestertown
  • Our hotel comes with a pool
  • 3 star Suburban hotel
More Photos Photo of Hampton Inn Middletown Pool
From$94
Very good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629
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~25.35 miles southeast of Chestertown
  • Has a pool!
  • 3-star Highway hotel
More Photos Pool image of Best Western Denton Inn
From$68
Very good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center in Baltimore 5625 O'donnell St., Baltimore, MD 21224
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~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Three Star Highway hotel
More Photos Photo of Best Western Plus Hotel & Conference Center Pool
From$72
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover 1706 North Dupont Highway, Dover, DE 19901
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~27.40 miles east of Chestertown
  • Includes a pool: Pool open daily form 8am-10pm.
  • Affordable Suburban property
More Photos Swimming pool at Hilton Garden Inn Dover
From$84
Very good 4.5 /5 Read 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 available: Open Daily 7:00 AM to 10:00 PM In-door Heated Pool
  • 4 star Resort property
More Photos Swimming pool at Bally's Dover Casino Resort
From$99
Very good 4.5 /5 Latest Reviews Call BookMore Details
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401
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~28.40 miles southwest of Chestertown
  • Has swimming pool: indoor pool. hours vary based upon season
  • 4-star Downtown property
More Photos Swimming pool at The Westin Annapolis
From$139
Very good 4.0 /5 Review Score Call BookMore Details
Comfort Inn & Suites : 764 Dover Leipsic Rd. 764 Dover Leipsic Rd., Dover, DE 19901
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~28.78 miles east of Chestertown
  • Includes a swimming pool
  • Three Star Suburban property
More Photos Photo of Comfort Inn & Suites Pool
From$83
Very good 4.5 /5 Review Score Call BookMore Details
Hyatt Place Baltimore Inner Harbor : 511 South Central Ave. 511 South Central Ave., Baltimore, MD 21202
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~28.89 miles west of Chestertown
  • Pool details: INDOOR POOL
  • Three Star Downtown property
More Photos Pool image of Hyatt Place Baltimore Inner Harbor
From$85
Very good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor 625b South President St., Baltimore, MD 21202
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~29.09 miles west of Chestertown
  • Has swimming pool
  • Three 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 - Baltimore 625a South President St., Baltimore, MD 21202
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~29.09 miles west of Chestertown
  • Our hotel comes with a pool
  • Three Star Downtown property
More Photos Swimming pool at Homewood Suites by Hilton Baltimore
From$80
Very good 4.5 /5 Read Reviews Call BookMore Details
Residence Inn Dover 600 Jefferic Blvd., Dover, DE 19901
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~29.10 miles east of Chestertown
  • Has swimming pool
  • Four star Suburban hotel
More Photos Swimming pool at Residence Inn Dover
From$125
Average 3.0 /5 Hotel Reviews Call BookMore Details
Wyndham Garden Dover Downtown 561 North Dupont Highway, Dover, DE 19901
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~29.11 miles east of Chestertown
  • Has swimming pool: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • 3-star Downtown hotel
More Photos Photo of Wyndham Garden Dover Downtown Pool
From$71
Average 3.0 /5 Read Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie 6600 Ritchie Highway, Glen Burnie, MD 21061
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~29.23 miles west of Chestertown
  • Includes a pool: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Two star Airport property
More Photos Photo of Red Roof Inn Baltimore South - Glen Burnie Pool
From$57
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601
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~29.32 miles south of Chestertown
  • Pool in hotel: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3 star Rural property
More Photos Pool image of Holiday Inn Express Easton
From$115
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn : 8523 Ocean Gateway 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 property
More Photos Pool image of Quality Inn
From$79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites 1 Center Dr., North East, MD 21901
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~29.39 miles north of Chestertown
  • Has swimming pool: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • Affordable Rural property
More Photos Swimming pool at Comfort Inn & Suites
From$67
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Inn 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.
  • Economy Suburban hotel
More Photos Pool image of Comfort Inn
From$56
Very good 4.0 /5 Reviews Call BookMore Details
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
  • 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 property
More Photos Photo of Hampton Inn & Suites Baltimore Inner Harbor Pool
From$89
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Hyatt Regency Baltimore Inner Harbor 300 Light St., Baltimore, MD 21202
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~29.71 miles west of Chestertown
  • With a pool!
  • High-end Convention Center hotel
More Photos Swimming pool at Hyatt Regency Baltimore Inner Harbor
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
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.
  • 3-star Suburban property
More Photos Photo of Crowne Plaza Annapolis An Ihg Hotel Pool
From$80
Very good 4.0 /5 Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor 222 Saint Paul Pl, Baltimore, MD 21202
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~29.79 miles west of Chestertown
  • Pool in hotel: No Pool available however we do offer a Complimentary Evening Reception Whether you''re winding down for the day or gearing up for the night, enjoy yourself at our complimentary Evening Reception. Choose from a variety of alcoholic* and non-alcoholic beverages while savoring light appetizers and great conversation. It''s more than perfect for adults and kids alike. *Service of alcohol subject to state and local laws. Must be of legal drinking age.
  • 4 star Downtown property
More Photos Pool image of Embassy Suites Baltimore Inner Harbor
From$69
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites in Annapolis Hampton Inn 124, Annapolis, MD 21401
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~29.81 miles southwest of Chestertown
  • Pool in hotel: Seasonal outdoor pool
  • Three Star Highway property
More Photos Swimming pool at Hampton Inn & Suites
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor - Baltimore 100 Hopkins Pl, Baltimore, MD 21201
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~29.93 miles west of Chestertown
  • Pool available: Outdoor pool (seasonal)
  • Midscale Downtown property
More Photos Photo of Days Inn by Wyndham Baltimore Inner Harbor Pool
From$73
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel in Towson 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.
  • 3 star Suburban property
More Photos Swimming pool at Holiday Inn Express Towson Baltimore North An Ihg Hotel
From$69
Very good 4.0 /5 Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis - Annapolis 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 Photo of Doubletree by Hilton Hotel Annapolis Pool
From$149
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Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401
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~30.17 miles southwest of Chestertown
  • Includes a pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 2 star Suburban hotel
More Photos Photo of Best Western Annapolis Pool
From$84
Average 3.0 /5 Guest Reviews Call BookMore Details
Wingate by Wyndham North East in 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 hotel
More Photos Pool image of Wingate by Wyndham North East
From$71
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Annapolis in Annapolis 124 Womack Dr., Annapolis, MD 21401
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~30.39 miles southwest of Chestertown
  • Includes a pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3-star Suburban property
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
  • Includes a pool: Seasonal Outdoor Pool
  • Mid-scale Suburban hotel
More Photos Pool image of Sonesta Es Suites Annapolis
From$99
Very good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Galaxy Inn : 1700 East Lebanon Rd. 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.
  • Mid-scale Suburban property
More Photos Photo of Best Western Galaxy Inn Pool
From$70
Average 3.5 /5 Recent Reviews Call BookMore Details
Hampton / Home2 Suites Towson - Towson 21 West Susquehanna Ave., Towson, MD 21204
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~31.53 miles west of Chestertown
  • Pool in hotel: Indoor Pool 9 AM - 10 PM
  • 3-star Downtown property
More Photos Photo of Hampton / Home2 Suites Towson Pool
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Sheraton Baltimore North Hotel in Towson 903 Dulaney Valley Rd., Towson, MD 21204
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~31.60 miles west of Chestertown
  • Includes a pool: Hotel has an indoor pool with life guard on duty. Pool hours vary will need to consult your sales manager if mandatory times are required
  • High-end Suburban property
More Photos Pool image of Sheraton Baltimore North Hotel
From$103
Very good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Elkton - Elkton 2 Warner Rd., Elkton, MD 21921
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~32.48 miles northeast of Chestertown
  • Pool available: 9am- 10pm
  • Three Star Highway property
More Photos Photo of Hampton Inn Elkton Pool
From$119
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Delta Marriott Baltimore North in Baltimore 5100 Falls Rd., Baltimore, MD 21210
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~32.56 miles west of Chestertown
  • Pool in hotel: Large Outdoor Seasonal Pool staffed with lifeguard, open 10 am - dusk daily, Memorial Day to Labor Day.
  • 3-star Suburban property
More Photos Swimming pool at Delta Marriott Baltimore North
From$74
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Holiday Inn Express & Suites Baltimore BWI North in Linthicum Heights 1510 Aero Dr., Linthicum Heights, MD 21090
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~32.62 miles west of Chestertown
  • Includes a pool: M-F 10a-10p Weekends 10a-10p Indoor Heated Pool No Lifeguard
  • Midscale Airport hotel
More Photos Photo of Holiday Inn Express & Suites Baltimore BWI North Pool
From$99
Very good 4.0 /5 Guest Reviews Call BookMore Details

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