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 in Grasonville 101 Vfw Ave., Grasonville, MD 21638
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~18.54 miles southwest of Chestertown
  • Includes a pool
  • Two-star Resort property
More Photos Pool image of Quality Inn Grasonville near Kent Island
From$88 total
Very Good 4.0 /5 Reviews Call BookMore Details
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Best Western Kent Narrows Inn 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.
  • 3 star Resort property
More Photos Swimming pool at Best Western Kent Narrows Inn
From$84 total
Average 3.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md - Aberdeen 20 Newton Rd., Aberdeen, MD 21001
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~20.61 miles north of Chestertown
  • Has swimming pool: **Pool is temporarily closed for extensive maintenance.
  • Economy Suburban hotel
More Photos Photo of Home2 Suites by Hilton Baltimore / Aberdeen Md Pool
From$72 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel in Belcamp 1326 Policy Dr., Belcamp, MD 21017
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~20.96 miles northwest of Chestertown
  • Has swimming pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Affordable Suburban property
More Photos Swimming pool at Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
From$96 total
Average 3.0 /5 Read Reviews Call BookMore Details
Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040
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~21.05 miles northwest of Chestertown
  • Our hotel comes with a pool
  • Midscale Suburban property
More Photos Pool image of Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
From$64 total
Average 3.0 /5 Read Reviews 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
  • Pool details: Our indoor heated pool is open from 7 am to 10 pm.
  • Midscale Rural property
More Photos Swimming pool at Towneplace Suites Edgewood Aberdeen
From$106 total
Average 3.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air 4170 Philadelphia Rd., Bel Air, MD 21015
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~21.26 miles northwest of Chestertown
  • Pool details: 9 AM - 10 PM During Covid 19 we are limiting the amount of people in pool area and scheduling pool time at front desk
  • Mid-scale Suburban property
More Photos Photo of Homewood Suites by Hilton Bel Air Pool
From$190 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD : 1435 Handlir Dr. 1435 Handlir Dr., Bel Air, MD 21015
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~21.29 miles northwest of Chestertown
  • Includes a pool: Outdoor Pool, open Memorial Day - Labor Day
  • Affordable Rural hotel
More Photos Swimming pool at Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
From$94 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South - Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040
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~21.33 miles northwest of Chestertown
  • Includes a pool: Indoor Pool available 6AM to 10PM
  • Affordable Suburban hotel
More Photos Pool image of Hampton Inn & Suites Edgewood/Aberdeen-South
From$114 total
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Aberdeen 1050 Beards Hill Rd., Aberdeen, MD 21001
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~22.48 miles north of Chestertown
  • Includes a pool: FREE INDOOR W/ HOT TUB
  • Mid-scale Suburban hotel
More Photos Pool image of Hilton Garden Inn Aberdeen
From$132 total
Very Good 4.0 /5 Hotel 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.
  • Three Star Highway property
More Photos Photo of Holiday Inn Express Aberdeen by IHG Pool
From$176 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen 795 West Bel Air Ave., Aberdeen, MD 21001
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~22.63 miles north of Chestertown
  • Pool available: Indoor pool
  • Cheap Highway hotel
More Photos Photo of Hampton Inn & Suites Baltimore/Aberdeen Pool
From$106 total
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Fairfield Inn N Stes Marriott in Aberdeen 907 Barnett Lane, Aberdeen, MD 21001
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~22.77 miles north of Chestertown
  • Our hotel comes with a pool
  • Affordable hotel
More Photos hotel room
From$108 total
Very Good 4.0 /5 Latest 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
  • Three Star Suburban hotel
More Photos Swimming pool at Country Inn & Suites by Radisson, Baltimore North, MD
From$96 total
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh - Baltimore 8477 Cordon Way, Baltimore, MD 21236
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~23.93 miles west of Chestertown
  • Pool details: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • Three Star Suburban hotel
More Photos Swimming pool at Fairfield Inn & Suites by Marriott White Marsh
From$106 total
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Holiday Inn Exp Stes Middletown : 315 Auto Park Dr. 315 Auto Park Dr., Middletown, DE 19709
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~24.19 miles northeast of Chestertown
  • Has swimming pool: Indoor Pool, open year round
  • Affordable Suburban property
More Photos Pool image of Holiday Inn Exp Stes Middletown
From$84 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn Middletown 117 Sandhill Dr., Middletown, DE 19709
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~24.53 miles northeast of Chestertown
  • Includes a pool
  • Mid-scale Suburban hotel
More Photos Swimming pool at Hampton Inn Middletown
From$112 total
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Denton Inn 521 Fleetwood Rd., Denton, MD 21629
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~25.35 miles southeast of Chestertown
  • Includes a pool
  • Affordable Highway property
More Photos Swimming pool at Best Western Denton Inn
From$81 total
Very Good 4.0 /5 Guest 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
  • Pool available: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Affordable Highway hotel
More Photos Photo of Best Western Plus Hotel & Conference Center Pool
From$86 total
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
  • Pool available: Pool open daily form 8am-10pm.
  • Midscale Suburban hotel
More Photos Swimming pool at Hilton Garden Inn Dover
From$100 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Bally's Dover Casino Resort : 1131 North Dupont Highway 1131 North Dupont Highway, Dover, DE 19901
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~28.36 miles east of Chestertown
  • Pool details: 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$118 total
Very Good 4.5 /5 Guest Reviews Call BookMore Details
The Westin Annapolis in Annapolis 100 Westgate Cir, Annapolis, MD 21401
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~28.40 miles southwest of Chestertown
  • Pool available: indoor pool. hours vary based upon season
  • 4 star Downtown property
More Photos Photo of The Westin Annapolis Pool
From$166 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites in Dover 764 Dover Leipsic Rd., Dover, DE 19901
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~28.78 miles east of Chestertown
  • With a pool!
  • Midscale Suburban hotel
More Photos Photo of Comfort Inn & Suites Pool
From$99 total
Very Good 4.5 /5 Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor in Baltimore 511 South Central Ave., Baltimore, MD 21202
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~28.89 miles west of Chestertown
  • Includes a pool: INDOOR POOL
  • Mid-scale Downtown property
More Photos Photo of Hyatt Place Baltimore Inner Harbor Pool
From$102 total
Very Good 4.0 /5 Latest 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
  • We have a pool
  • 3 star Downtown property
More Photos Pool image of Hilton Garden Inn Baltimore Inner Harbor
From$132 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore 625a South President St., Baltimore, MD 21202
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~29.09 miles west of Chestertown
  • Has a pool!
  • 3 star Downtown hotel
More Photos Pool image of Homewood Suites by Hilton Baltimore
From$96 total
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Residence Inn Dover in Dover 600 Jefferic Blvd., Dover, DE 19901
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~29.10 miles east of Chestertown
  • Has swimming pool
  • 4-star Suburban hotel
More Photos Swimming pool at Residence Inn Dover
From$150 total
Average 3.0 /5 Read Reviews Call BookMore Details
Wyndham Garden Dover Downtown in Dover 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.
  • Three Star Downtown hotel
More Photos Pool image of Wyndham Garden Dover Downtown
From$85 total
Average 3.0 /5 Latest Reviews Call BookMore Details
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
  • 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$68 total
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Easton : 8561 Ocean Gateway 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 Pool image of Holiday Inn Express Easton
From$138 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Quality Inn 8523 Ocean Gateway, Easton, MD 21601
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~29.37 miles south of Chestertown
  • Pool available: 9:00am-9:00pm Outdoor Pool
  • Low-priced Rural property
More Photos Photo of Quality Inn Pool
From$94 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr. 1 Center Dr., North East, MD 21901
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~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.
  • Mid-scale Rural hotel
More Photos Photo of Comfort Inn & Suites Pool
From$80 total
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn - Towson 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.
  • Low priced Suburban property
More Photos Pool image of Comfort Inn
From$67 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Renaissance Baltimore Harborplace Hotel 202 East Pratt St., Baltimore, MD 21202
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~29.62 miles west of Chestertown
  • With a pool!
  • High end Downtown property
More Photos Photo of Renaissance Baltimore Harborplace Hotel Pool
From$172 total
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor in Baltimore 131 East Redwood St., Baltimore, MD 21202
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~29.67 miles west of Chestertown
  • Pool available: 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.
  • 3 star Downtown hotel
More Photos Pool image of Hampton Inn & Suites Baltimore Inner Harbor
From$106 total
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor 300 Light St., Baltimore, MD 21202
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~29.71 miles west of Chestertown
  • We have a pool ready for use
  • High-end Convention Center hotel
More Photos Photo of Hyatt Regency Baltimore Inner Harbor Pool
From$150 total
Average 3.0 /5 Recent Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel : 173 Jennifer Rd. 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 Pool image of Crowne Plaza Annapolis An Ihg Hotel
From$96 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor in Baltimore 222 Saint Paul Pl, Baltimore, MD 21202
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~29.79 miles west of Chestertown
  • Has swimming pool: 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.
  • Expensive Downtown property
More Photos Pool image of Embassy Suites Baltimore Inner Harbor
From$82 total
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Hampton Inn 124, Annapolis, MD 21401
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~29.81 miles southwest of Chestertown
  • Has swimming pool: Seasonal outdoor pool
  • Mid-scale Highway hotel
More Photos Pool image of Hampton Inn & Suites
From$96 total
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
  • Pool available: Outdoor pool (seasonal)
  • Mid-scale Downtown hotel
More Photos Pool image of Days Inn by Wyndham Baltimore Inner Harbor
From$87 total
Very Good 4.0 /5 Reviews Call BookMore Details
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
  • Pool details: 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.
  • Three Star Suburban property
More Photos Pool image of Holiday Inn Express Towson Baltimore North An Ihg Hotel
From$82 total
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis in Annapolis 210 Holiday Court, Annapolis, MD 21401
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~30.10 miles southwest of Chestertown
  • Includes a pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • 3 star Suburban hotel
More Photos Photo of Doubletree by Hilton Hotel Annapolis Pool
From$178 total
Average 3.0 /5 Latest Reviews Call BookMore Details
Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401
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~30.17 miles southwest of Chestertown
  • Pool details: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Two-star Suburban hotel
More Photos Swimming pool at Best Western Annapolis
From$100 total
Average 3.0 /5 Reviews Call BookMore Details
Wingate by Wyndham North East - North East 39 Elwoods Rd., North East, MD 21901
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~30.29 miles north of Chestertown
  • Includes a pool: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • Affordable Rural property
More Photos Photo of Wingate by Wyndham North East Pool
From$85 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Annapolis : 124 Womack Dr. 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.
  • Three Star Suburban property
More Photos Swimming pool at Hampton Inn & Suites Annapolis
From$84 total
Very Good 4.0 /5 Read Reviews Call BookMore Details
Sonesta Es Suites Annapolis 170 Admiral Cochrane Dr., Annapolis, MD 21401
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~30.57 miles southwest of Chestertown
  • Pool available: Seasonal Outdoor Pool
  • Midscale Suburban property
More Photos Pool image of Sonesta Es Suites Annapolis
From$118 total
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Galaxy Inn 1700 East Lebanon Rd., Dover, DE 19901
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~31.11 miles east of Chestertown
  • Pool available: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • 3 star Suburban hotel
More Photos Photo of Best Western Galaxy Inn Pool
From$84 total
Average 3.5 /5 Latest Reviews Call BookMore Details
Hampton / Home2 Suites Towson in Towson 21 West Susquehanna Ave., Towson, MD 21204
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~31.53 miles west of Chestertown
  • Includes a pool: Indoor Pool 9 AM - 10 PM
  • Three Star Downtown hotel
More Photos Swimming pool at Hampton / Home2 Suites Towson
From$96 total
Average 3.0 /5 Guest Reviews Call BookMore Details
Sheraton Baltimore North Hotel : 903 Dulaney Valley Rd. 903 Dulaney Valley Rd., Towson, MD 21204
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~31.60 miles west of Chestertown
  • Has swimming 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
  • 4-star Suburban property
More Photos Swimming pool at Sheraton Baltimore North Hotel
From$123 total
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Elkton 2 Warner Rd., Elkton, MD 21921
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~32.48 miles northeast of Chestertown
  • Includes a pool: 9am- 10pm
  • Mid-scale Highway hotel
More Photos Swimming pool at Hampton Inn Elkton
From$142 total
Very Good 4.0 /5 Read Reviews Call BookMore Details

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