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.
Planning group travel? Get Chestertown MD Group Hotel Rates

Chestertown Hotels with Outdoor or Indoor Pools

Quality Inn 101 Vfw Ave., Grasonville, MD 21638 Call ~18.54 miles southwest of Chestertown
  • Our hotel comes with a pool
  • 2 star Resort hotel
More Photos
From$74
Very good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Kent Narrows Inn 3101 Main St., Grasonville, MD 21638 Call ~19.04 miles southwest of Chestertown
  • Pool in hotel: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • 3-star Resort hotel
More Photos
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Kent Island Marina 3206 Main St., Grasonville, MD 21638 Call ~19.08 miles southwest of Chestertown
  • Pool details: Indoor pool open daily 5 AM-11PM
  • 3 star Riverfront hotel
More Photos
From$121
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel : 1326 Policy Dr. 1326 Policy Dr., Belcamp, MD 21017 Call ~20.96 miles northwest of Chestertown
  • Pool available: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban hotel
More Photos
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area in Edgewood 1807 Edgewood Rd., Edgewood, MD 21040 Call ~21.05 miles northwest of Chestertown
  • Our hotel comes with a pool
  • Affordable Suburban hotel
More Photos
From$54
Average 3.0 /5 Review Score Call BookMore Details
Towneplace Suites Edgewood Aberdeen 1357 Belcamp Rd., Belcamp, MD 21017 Call ~21.21 miles northwest of Chestertown
  • Pool details: Our indoor heated pool is open from 7 am to 10 pm.
  • Affordable Rural hotel
More Photos
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South : 2110 Emmorton Park Rd. 2110 Emmorton Park Rd., Edgewood, MD 21040 Call ~21.33 miles northwest of Chestertown
  • Includes a pool: Indoor Pool available 6AM to 10PM
  • Midscale Suburban hotel
More Photos
From$95
Very good 4.0 /5 Read Reviews Call BookMore Details
Kent Island Resort 500 Kent Manor Dr., Stevensville, MD 21666 Call ~21.50 miles southwest of Chestertown
  • Pool in hotel: Outdoor (seasonal pool)
  • High end Riverfront property
More Photos
From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Aberdeen - Aberdeen 1050 Beards Hill Rd., Aberdeen, MD 21001 Call ~22.48 miles north of Chestertown
  • Has swimming pool: FREE INDOOR W/ HOT TUB
  • Mid-scale Suburban hotel
More Photos
From$110
Very good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG : 1007 Beards Hill Rd. 1007 Beards Hill Rd., Aberdeen, MD 21001 Call ~22.51 miles north of Chestertown
  • Includes a pool: 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
From$147
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Baltimore / Aberdeen in Aberdeen 795 West Bel Air Ave., Aberdeen, MD 21001 Call ~22.63 miles north of Chestertown
  • Pool in hotel: Indoor pool
  • Economy Highway property
More Photos
From$89
Very good 4.5 /5 Review Score Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg 980 Hospitality Way, Aberdeen, MD 21001 Call ~22.75 miles north of Chestertown
  • Pool in hotel: Seasonal Large Outdoor Pool with picnic tables and grills
  • Three Star Highway property
More Photos
From$84
Average 3.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn N Stes Marriott : 907 Barnett Lane 907 Barnett Lane, Aberdeen, MD 21001 Call ~22.77 miles north of Chestertown
  • Includes a swimming pool
  • Affordable hotel
More Photos
From$90
Very good 4.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh : 5015 Campbell Blvd. 5015 Campbell Blvd., Baltimore, MD 21236 Call ~23.76 miles west of Chestertown
  • Includes a pool: Indoor Pool
  • Mid-scale Suburban property
More Photos
From$89
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh - Nottingham 8225 Town Center Dr., Nottingham, MD 21236 Call ~23.79 miles west of Chestertown
  • Pool details: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • Affordable Suburban hotel
More Photos
From$89
Very good 4.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites by Radisson, Baltimore North, MD 8825 Yellow Brick Rd., Rosedale, MD 21237 Call ~23.90 miles west of Chestertown
  • Pool in hotel: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Mid-scale Suburban hotel
More Photos
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh 8477 Cordon Way, Baltimore, MD 21236 Call ~23.93 miles west of Chestertown
  • Includes a pool: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • Midscale Suburban hotel
More Photos
From$89
Very good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Denton Inn - Denton 521 Fleetwood Rd., Denton, MD 21629 Call ~25.35 miles southeast of Chestertown
  • We have a pool
  • 3 star Highway property
More Photos
From$68
Very good 4.0 /5 Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center 5625 O'donnell St., Baltimore, MD 21224 Call ~26.13 miles west of Chestertown
  • Pool available: Indoor heated pool Open 10 am - 10 pm, weekly.
  • 3-star Highway hotel
More Photos
From$72
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover 1706 North Dupont Highway, Dover, DE 19901 Call ~27.40 miles east of Chestertown
  • Has swimming pool: Pool open daily form 8am-10pm.
  • 3 star Suburban hotel
More Photos
From$84
Very good 4.5 /5 Review Score Call BookMore Details
Bally's Dover Casino Resort in Dover 1131 North Dupont Highway, Dover, DE 19901 Call ~28.36 miles east of Chestertown
  • Pool available: Open Daily 7:00 AM to 10:00 PM In-door Heated Pool
  • Four star Resort hotel
More Photos
From$99
Very good 4.5 /5 Latest Reviews Call BookMore Details
The Westin Annapolis 100 Westgate Cir, Annapolis, MD 21401 Call ~28.40 miles southwest of Chestertown
  • Includes a pool: indoor pool. hours vary based upon season
  • 4 star Downtown hotel
More Photos
From$139
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites 764 Dover Leipsic Rd., Dover, DE 19901 Call ~28.78 miles east of Chestertown
  • Has swimming pool
  • Three Star Suburban hotel
More Photos
From$83
Very good 4.5 /5 Read Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor : 511 South Central Ave. 511 South Central Ave., Baltimore, MD 21202 Call ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • 3 star Downtown property
More Photos
From$85
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor 625b South President St., Baltimore, MD 21202 Call ~29.09 miles west of Chestertown
  • Pool in hotel
  • Midscale Downtown property
More Photos
From$110
Very good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore 625a South President St., Baltimore, MD 21202 Call ~29.09 miles west of Chestertown
  • Has swimming pool
  • Three Star Downtown property
More Photos
From$80
Very good 4.5 /5 Hotel Reviews Call BookMore Details
Residence Inn Dover - Dover 600 Jefferic Blvd., Dover, DE 19901 Call ~29.10 miles east of Chestertown
  • We have a pool ready for use
  • 4-star Suburban hotel
More Photos
From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Wyndham Garden Dover Downtown 561 North Dupont Highway, Dover, DE 19901 Call ~29.11 miles east of Chestertown
  • Pool in hotel: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • Affordable Downtown hotel
More Photos
From$71
Average 3.0 /5 Read Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie 6323 Ritchie Highway, Glen Burnie, MD 21061 Call ~29.21 miles west of Chestertown
  • Pool details: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3-star Suburban hotel
More Photos
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie - Glen Burnie 6600 Ritchie Highway, Glen Burnie, MD 21061 Call ~29.23 miles west of Chestertown
  • Pool available: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Economy Airport hotel
More Photos
From$57
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601 Call ~29.32 miles south of Chestertown
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3-star Rural property
More Photos
From$115
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn : 8523 Ocean Gateway 8523 Ocean Gateway, Easton, MD 21601 Call ~29.37 miles south of Chestertown
  • Pool in hotel: 9:00am-9:00pm Outdoor Pool
  • 2-star Rural hotel
More Photos
From$79
Very good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr. 1 Center Dr., North East, MD 21901 Call ~29.39 miles north of Chestertown
  • Pool in hotel: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • 3-star Rural property
More Photos
From$67
Average 3.0 /5 Latest Reviews Call BookMore Details
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.
  • Cheap Suburban hotel
More Photos
From$56
Very good 4.0 /5 Read Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore 550 Light St., Baltimore, MD 21202 Call ~29.64 miles west of Chestertown
  • Pool in hotel: 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
More Photos
From$79
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor : 131 East Redwood St. 131 East Redwood St., Baltimore, MD 21202 Call ~29.67 miles west of Chestertown
  • Has swimming 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
More Photos
From$89
Very good 4.5 /5 Hotel Reviews Call BookMore Details
The Royal Sonesta Harbor Court in Baltimore 550 Light St., Baltimore, MD 21230 Call ~29.68 miles west of Chestertown
  • Includes a pool: Our rooftop indoor pool is open 5am-10pm daily
  • 4 star Downtown hotel
More Photos
From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor 300 Light St., Baltimore, MD 21202 Call ~29.71 miles west of Chestertown
  • Has swimming pool
  • Expensive Convention Center property
More Photos
From$125
Average 3.0 /5 Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel 173 Jennifer Rd., Annapolis, MD 21401 Call ~29.76 miles southwest of Chestertown
  • Pool in hotel: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Hours vary.
  • Midscale Suburban property
More Photos
From$80
Very good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Dover De 222 South Dupont Highway, Dover, DE 19901 Call ~29.76 miles east of Chestertown
  • Pool details: 6am - 10pm
  • Low priced Downtown property
More Photos
From$99
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites : Hampton Inn 124 Hampton Inn 124, Annapolis, MD 21401 Call ~29.81 miles southwest of Chestertown
  • Pool in hotel: Seasonal outdoor pool
  • Mid-scale Highway property
More Photos
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor in Baltimore 100 Hopkins Pl, Baltimore, MD 21201 Call ~29.93 miles west of Chestertown
  • Includes a pool: Outdoor pool (seasonal)
  • Three Star Downtown property
More Photos
From$73
Very good 4.0 /5 Reviews Call BookMore Details
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 available: 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.
  • Affordable Suburban hotel
More Photos
From$69
Very good 4.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis in Annapolis 210 Holiday Court, Annapolis, MD 21401 Call ~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
From$149
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401 Call ~30.17 miles southwest of Chestertown
  • Includes a pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Low priced Suburban hotel
More Photos
From$84
Average 3.0 /5 Hotel Reviews Call BookMore Details
Wingate by Wyndham North East - North East 39 Elwoods Rd., North East, MD 21901 Call ~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.
  • Affordable Rural hotel
More Photos
From$71
Very good 4.0 /5 Recent Reviews Call BookMore Details
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.
  • Three Star Suburban property
More Photos
From$70
Very good 4.0 /5 Guest Reviews Call BookMore Details
Sonesta Es Suites Annapolis 170 Admiral Cochrane Dr., Annapolis, MD 21401 Call ~30.57 miles southwest of Chestertown
  • Has swimming pool: Seasonal Outdoor Pool
  • 3 star Suburban property
More Photos
From$99
Very good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Galaxy Inn in Dover 1700 East Lebanon Rd., Dover, DE 19901 Call ~31.11 miles east of Chestertown
  • Pool details: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Three Star Suburban property
More Photos
From$70
Average 3.5 /5 Guest Reviews Call BookMore Details
Hampton / Home2 Suites Towson 21 West Susquehanna Ave., Towson, MD 21204 Call ~31.53 miles west of Chestertown
  • Pool in hotel: Indoor Pool 9 AM - 10 PM
  • 3 star Downtown hotel
More Photos
From$80
Average 3.0 /5 Review Score Call BookMore Details
Back to Top