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Hotel Name
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Chestertown Hotels with Outdoor or Indoor Pools

Best Western Kent Narrows Inn in Grasonville 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Pool available: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Two star Resort hotel
Hilton Garden Inn Kent Island 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Includes a pool: Indoor pool open daily 6 AM-10PM
  • Three Star Riverfront hotel
From$132
Very Good 4.5 /5Guest Reviews Call
Home2 Suites by Hilton Aberdeen 20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Pool details: Indor Saline Pool Open Daily 9am - 10pm
  • Three Star Suburban hotel
Wingate by Wyhdham 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 8am - 10pm daily.
  • Affordable Suburban hotel
Sleep Inn & Suites - Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Has swimming pool
  • Cheap Suburban property
Comfort Inn & Suites Edgewood Aberdeen Bel Air : 2112a Emmorton Park Rd. 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Pool available: Indoor Heated Open Daily 6AM-10PM
  • Cheap Suburban property
Homewood Suites by Hilton in Bel Air
+1-888-690-5281
4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Includes a pool
  • Mid-scale Suburban property
From$124
Very Good 4.5 /5Hotel Reviews Call
Springhill Suites by Marriott Edgewood Aberdeen - Bel Air 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Our hotel comes with a pool
  • 3 star Highway hotel
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Pool available: Outdoor Pool, open Memorial Day - Labor Day
  • Three Star Rural property
From$75
Very Good 4.5 /5Review Score Call
Hampton Inn & Suites Edgewood / Aberdeen South in Edgewood 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Pool details: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban hotel
From$89
Very Good 4.5 /5Read Reviews Call
Holiday Inn Express Aberdeen : 1007 Beards Hill Rd. 1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.54 miles north of Chestertown
  • Includes a pool: Enjoy a relaxing "dip" in our indoor-heated pool. The pool is located on the first floor and is open daily from 8am-10pm.
  • Mid-scale Highway hotel
Travelodge Hotel - Aberdeen
+1-800-997-5149
820 West Bel Air Ave., Aberdeen, MD 21001 ~22.70 miles north of Chestertown
  • Includes a pool: Seasonal Outdoor PoolMay to September
  • Two star Downtown hotel
Comfort Inn & Suites Aberdeen - Aberdeen 980 Hospitality Way, Aberdeen, MD 21001 ~22.79 miles north of Chestertown
  • Has swimming pool: Seasonal Outdoor Pool
  • Affordable Highway property
Residence Inn Baltimore White Marsh
+1-800-230-4134
4980 Mercantile Rd., White Marsh, MD 21236 ~23.88 miles west of Chestertown
  • Pool in hotel
  • 3-star Suburban hotel
From$103
Very Good 4.0 /5Recent Reviews Call
Hampton Inn in Baltimore 8225 Town Center Dr., Baltimore, MD 21236 ~23.91 miles west of Chestertown
  • Pool available: Outdoor Heated Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with gas grill available for guests to use.
  • 3 star Downtown hotel
From$149
Very Good 4.5 /5Read Reviews Call
Country Inn & Suites Baltimore North 8825 Yellow Brick Rd., Baltimore, MD 21237 ~23.92 miles west of Chestertown
  • Includes a swimming pool
  • Midscale Suburban property
From$149
Very Good 4.0 /5Read Reviews Call
Fairfield Inn & Suites 8477 Cordon Way, Baltimore, MD 21236 ~23.94 miles west of Chestertown
  • Pool in hotel
  • Affordable Suburban hotel
La Quinta Inn & Suites Baltimore North - Baltimore 4 Philadelphia Court, Baltimore, MD 21237 ~24.40 miles west of Chestertown
  • Has swimming pool: Outdoor Pool open Memorial Day weekend through Labor Day weekend.
  • Midscale Suburban hotel
Best Western Plus Hotel & Conference Center - Baltimore 5625 O'donnell St., Baltimore, MD 21224 ~26.14 miles west of Chestertown
  • Pool details: Indoor heated pool with lifeguard on duty. Open 10 am - 10 pm, weekly.
  • Midscale Highway property
Hilton Garden Inn Dover : 1706 North Dupont Highway 1706 North Dupont Highway, Dover, DE 19901 ~27.43 miles east of Chestertown
  • Includes a pool
  • Midscale Suburban property
Hampton Inn Dover 1568 North Dupont Highway, Dover, DE 19901 ~27.65 miles east of Chestertown
  • Our hotel comes with a pool
  • Two star Suburban hotel
Harbourtowne Golf Resort & Conference Center 9784 Martingham Dr., Saint Michaels, MD 21663 ~28.37 miles south of Chestertown
  • Pool in hotel: May - SeptemberOlympic Size Outdoor Pool with Lifeguard
  • Mid-scale Riverfront property
From$99
Average 3.5 /5Reviews Call
Dover Downs Hotel & Casino 1131 North Dupont Highway, Dover, DE 19901 ~28.41 miles east of Chestertown
  • Includes a pool: Open Daily 7:00 AM to 10:00 PMIn-door Heated Pool
  • High-end Resort property
From$89
Very Good 4.0 /5Read Reviews Call
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 ~28.48 miles southwest of Chestertown
  • Pool details: indoor pool. lifeguard on duty. hours vary based upon season
  • 4-star Downtown hotel
From$109
Very Good 4.0 /5Read Reviews Call
Comfort Inn & Suites 764 Dover Leipsic Rd., Dover, DE 19901 ~28.83 miles east of Chestertown
  • Includes a pool
  • 3-star Suburban hotel
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