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Chestertown Hotels with Outdoor or Indoor Pools

Holiday Inn Express & Suites : 150 Scheeler Rd. +1-800-230-4134 150 Scheeler Rd., Chestertown, MD 21620
  • Includes a pool: Indoor heated pool. Open 8am-10pm
  • 3-star Suburban property
From$87
Very Good 4.0 /5Guest Reviews
Best Western Kent Narrows Inn in Grasonville +1-800-997-5148 3101 Main St., Grasonville, MD 21638 ~19.10 miles southwest of Chestertown
  • Pool details: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Economy Resort property
From$75
Average 3.5 /5Reviews
Hilton Garden Inn Kent Island : 3206 Main St. +1-888-205-8144 3206 Main St., Grasonville, MD 21638 ~19.11 miles southwest of Chestertown
  • Pool in hotel: Indoor pool open daily 6 AM-10PM
  • 3 star Riverfront hotel
From$164
Very Good 4.5 /5Review Score
Wingate by Wyhdham in Belcamp +1-800-997-5149 1326 Poilicy Dr., Belcamp, MD 21017 ~20.99 miles northwest of Chestertown
  • Pool details: Indoor Heated Pool. Open from 8am - 10pm daily.
  • Three Star Suburban hotel
From$64
Average 3.5 /5Guest Reviews
Sleep Inn & Suites : 1807 Edgewood Rd. +1-800-230-4134 1807 Edgewood Rd., Edgewood, MD 21040 ~21.07 miles northwest of Chestertown
  • Has a pool!
  • Two star Suburban property
From$69
Average 3.5 /5Reviews
Comfort Inn & Suites Aberdeen Proving Grounds Area : 2112a Emmorton Park Rd. +1-800-997-5148 2112a Emmorton Park Rd., Edgewood, MD 21040 ~21.27 miles northwest of Chestertown
  • Pool details: Hotel features an indoor pool
  • Two-star Suburban hotel
From$60
Very Good 4.5 /5Guest Reviews
Homewood Suites by Hilton in Bel Air +1-888-205-8144 4170 Philadelphia Rd., Bel Air, MD 21015 ~21.28 miles northwest of Chestertown
  • Includes a pool
  • Midscale Suburban property
From$129
Very Good 4.5 /5Hotel Reviews
Springhill Suites by Marriott Edgewood Aberdeen : 1420 Handlir Dr. +1-800-997-5149 1420 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • We have a pool
  • Midscale Highway property
From$99
Very Good 4.0 /5Hotel Reviews
Country Inn & Suites Bel Air E. (Aberdeen) at I 95 +1-800-230-4134 1435 Handlir Dr., Bel Air, MD 21015 ~21.31 miles northwest of Chestertown
  • Pool details: Outdoor Pool, open Memorial Day - Labor Day
  • 3 star Rural hotel
From$75
Very Good 4.5 /5Recent Reviews
Hampton Inn & Suites Edgewood / Aberdeen South +1-800-997-5148 2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.37 miles northwest of Chestertown
  • Pool available: Indoor Pool available 6AM to 10PM
  • Affordable Suburban property
From$89
Very Good 4.5 /5Recent Reviews
Holiday Inn Express Aberdeen : 1007 Beards Hill Rd. +1-888-205-8144 1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.54 miles north of Chestertown
  • Pool available: 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
From$109
Average 3.5 /5Reviews
La Quinta Inn Aberdeen Md +1-800-997-5149 793 West Bel Air Ave., Aberdeen, MD 21001 ~22.67 miles north of Chestertown
  • With a pool!
  • Low-priced Rural hotel
From$69
Average 3.0 /5Latest Reviews
Merit Hotel & Suites Aberdeen in Aberdeen +1-800-230-4134 980 Hospitality Way, Aberdeen, MD 21001 ~22.70 miles north of Chestertown
  • Includes a pool: Seasonal
  • Three Star Highway property
From$52
Average 3.0 /5Recent Reviews
Travelodge Hotel : 820 West Bel Air Ave. +1-800-997-5148 820 West Bel Air Ave., Aberdeen, MD 21001 ~22.70 miles north of Chestertown
  • Has swimming pool: Seasonal Outdoor PoolMay to September
  • Two star Downtown property
From$41
Average 3.0 /5Read Reviews
Hampton Inn : 8225 Town Center Dr. +1-888-205-8144 8225 Town Center Dr., Baltimore, MD 21236 ~23.91 miles west of Chestertown
  • Pool details: Outdoor Heated Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with gas grill available for guests to use.
  • Midscale Downtown hotel
From$129
Very Good 4.5 /5Review Score
Country Inn & Suites Baltimore North - Baltimore +1-800-997-5149 8825 Yellow Brick Rd., Baltimore, MD 21237 ~23.92 miles west of Chestertown
  • Has swimming pool
  • Mid-scale Suburban hotel
From$79
Very Good 4.0 /5Hotel Reviews
Fairfield Inn & Suites in Baltimore +1-800-230-4134 8477 Cordon Way, Baltimore, MD 21236 ~23.94 miles west of Chestertown
  • With a pool!
  • 3 star Suburban property
From$71
Very Good 4.5 /5Review Score
La Quinta Inn & Suites Baltimore North in Baltimore +1-800-997-5148 4 Philadelphia Court, Baltimore, MD 21237 ~24.40 miles west of Chestertown
  • Includes a pool: Outdoor Pool open Memorial Day weekend through Labor Day weekend.
  • Midscale Suburban property
From$65
Average 3.5 /5Read Reviews
Best Western Plus Hotel & Conference Center - Baltimore +1-888-205-8144 5625 O'donnell St., Baltimore, MD 21224 ~26.14 miles west of Chestertown
  • Pool in hotel: Indoor heated pool with lifeguard on duty. Open 10 am - 10 pm, weekly.
  • Mid-scale Highway hotel
From$66
Average 3.5 /5Guest Reviews
Hilton Garden Inn Dover +1-800-997-5149 1706 North Dupont Highway, Dover, DE 19901 ~27.43 miles east of Chestertown
  • Has swimming pool
  • 3 star Suburban hotel
From$89
Very Good 4.5 /5Reviews
Hampton Inn Dover in Dover +1-800-230-4134 1568 North Dupont Highway, Dover, DE 19901 ~27.65 miles east of Chestertown
  • We have a pool ready for use
  • 2 star Suburban property
From$50
Very Good 4.0 /5Guest Reviews
Harbourtowne Golf Resort +1-800-997-5148 9784 Martingham Dr., Saint Michaels, MD 21663 ~28.37 miles south of Chestertown
  • Includes a pool: Memorial day to Labor day.Outdoor
  • Mid-scale Riverfront hotel
From$119
Average 3.5 /5Read Reviews
The Westin Annapolis +1-888-205-8144 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 /5Latest Reviews
Comfort Inn & Suites : 764 Dover Leipsic Rd. +1-800-997-5149 764 Dover Leipsic Rd., Dover, DE 19901 ~28.83 miles east of Chestertown
  • Includes a swimming pool
  • Mid-scale Suburban property
From$85
Very Good 4.5 /5Recent Reviews
Hyatt Place Baltimore Inner Harbor East +1-800-230-4134 511 South Central Ave., Baltimore, MD 21202 ~28.92 miles west of Chestertown
  • Pool in hotel: Outdoor Pool - open from Memorial Day to Labor Day
  • Three Star Downtown property
From$85
Very Good 4.5 /5Review Score
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