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
+1-888-389-4121

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101 Vfw Ave., Grasonville, MD 21638 ~18.54 miles southwest of Chestertown
  • Includes a pool
  • Cheap Resort hotel
More Photos Photo of Quality Inn Grasonville near Kent Island Pool
From$74
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Best Western Kent Narrows Inn in Grasonville
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
3101 Main St., Grasonville, MD 21638 ~19.04 miles southwest of Chestertown
  • Pool in hotel: 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$70
Average 3.0 /5 Latest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Pool available: **Pool is temporarily closed for extensive maintenance.
  • Cheap Suburban property
More Photos Pool image of Home2 Suites by Hilton Baltimore / Aberdeen Md
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel in Belcamp
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1326 Policy Dr., Belcamp, MD 21017 ~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • 3 star Suburban property
More Photos Pool image of Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
+1-888-965-1860

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1807 Edgewood Rd., Edgewood, MD 21040 ~21.05 miles northwest of Chestertown
  • Includes a pool
  • Mid-scale Suburban property
More Photos Swimming pool at Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
From$54
Average 3.0 /5 Hotel Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen in Belcamp
+1-888-788-5576

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1357 Belcamp Rd., Belcamp, MD 21017 ~21.21 miles northwest of Chestertown
  • Pool details: Our indoor heated pool is open from 7 am to 10 pm.
  • Affordable Rural property
More Photos Swimming pool at Towneplace Suites Edgewood Aberdeen
From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air
+1-888-897-9207

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4170 Philadelphia Rd., Bel Air, MD 21015 ~21.26 miles northwest of Chestertown
  • Has swimming pool: 9 AM - 10 PM During Covid 19 we are limiting the amount of people in pool area and scheduling pool time at front desk
  • Three Star Suburban hotel
More Photos Swimming pool at Homewood Suites by Hilton Bel Air
From$159
Very Good 4.0 /5 Read Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD in Bel Air
+1-888-311-4278

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1435 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Pool in hotel: Outdoor Pool, open Memorial Day - Labor Day
  • Affordable Rural property
More Photos Pool image of Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
From$79
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South
+1-888-469-4795

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2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.33 miles northwest of Chestertown
  • Pool details: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban property
More Photos Pool image of Hampton Inn & Suites Edgewood/Aberdeen-South
From$95
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.48 miles north of Chestertown
  • Pool details: FREE INDOOR W/ HOT TUB
  • Mid-scale Suburban property
More Photos Swimming pool at Hilton Garden Inn Aberdeen
From$110
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG - Aberdeen
+1-888-841-5292

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1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • Has swimming 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.
  • Mid-scale Highway property
More Photos Photo of Holiday Inn Express Aberdeen by IHG Pool
From$147
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen - Aberdeen
+1-888-455-5160

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795 West Bel Air Ave., Aberdeen, MD 21001 ~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • Low Cost Highway hotel
More Photos Photo of Hampton Inn & Suites Baltimore/Aberdeen Pool
From$89
Very Good 4.5 /5 Guest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen Apg : 793 West Bel Air Ave.
+1-888-965-8297

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793 West Bel Air Ave., Aberdeen, MD 21001 ~22.66 miles north of Chestertown
  • Pool in hotel
  • Affordable Rural hotel
More Photos hotel room
From$80
Average 3.0 /5 Reviews Call BookMore Details
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Fairfield Inn N Stes Marriott : 907 Barnett Lane
+1-888-906-6358

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907 Barnett Lane, Aberdeen, MD 21001 ~22.77 miles north of Chestertown
  • We have a pool ready for use
  • Three Star property
More Photos hotel room
From$90
Very Good 4.0 /5 Reviews Call BookMore Details
Country Inn & Suites by Radisson, Baltimore North, MD
+1-888-749-6785

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8825 Yellow Brick Rd., Rosedale, MD 21237 ~23.90 miles west of Chestertown
  • Has swimming pool: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Affordable Suburban property
More Photos Pool image of Country Inn & Suites by Radisson, Baltimore North, MD
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
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Fairfield Inn & Suites by Marriott White Marsh in Baltimore
+1-888-878-9982

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8477 Cordon Way, Baltimore, MD 21236 ~23.93 miles west of Chestertown
  • Has swimming pool: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • 3 star 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
Holiday Inn Exp Stes Middletown : 315 Auto Park Dr.
+1-888-389-4485

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315 Auto Park Dr., Middletown, DE 19709 ~24.19 miles northeast of Chestertown
  • Includes a pool: Indoor Pool, open year round
  • Three Star Suburban property
More Photos Swimming pool at Holiday Inn Exp Stes Middletown
From$70
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Hampton Inn Middletown : 117 Sandhill Dr.
+1-888-389-4121

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117 Sandhill Dr., Middletown, DE 19709 ~24.53 miles northeast of Chestertown
  • Includes a pool
  • Three Star Suburban hotel
More Photos Swimming pool at Hampton Inn Middletown
From$94
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Denton Inn - Denton
+1-888-675-2083

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521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • Our hotel comes with a pool
  • Three Star Highway hotel
More Photos Swimming pool at Best Western Denton Inn
From$68
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Baltimore Bayview Campus
+1-800-716-8490

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6571 Eastern Ave., Baltimore, MD 21224 ~25.61 miles west of Chestertown
  • Pool available: Indoor/Heated Pool Lifeguard on duty M-F 5pm - 10pm Sat/Sun 9am -10pm Summer Fri 12p-10p
  • Three Star Suburban hotel
More Photos Pool image of Hampton Inn Baltimore Bayview Campus
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center : 5625 O'donnell St.
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
5625 O'donnell St., Baltimore, MD 21224 ~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Three Star Highway hotel
More Photos Pool image of Best Western Plus Hotel & Conference Center
From$72
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Pool available: Pool open daily form 8am-10pm.
  • 3 star Suburban property
More Photos Pool image of Hilton Garden Inn Dover
From$84
Very Good 4.5 /5 Review Score Call BookMore Details
Bally's Dover Casino Resort
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1131 North Dupont Highway, Dover, DE 19901 ~28.36 miles east of Chestertown
  • Pool details: Open Daily 7:00 AM to 10:00 PM In-door Heated Pool
  • Four-star Resort hotel
More Photos Photo of Bally's Dover Casino Resort Pool
From$99
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
The Westin Annapolis in Annapolis
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 ~28.40 miles southwest of Chestertown
  • Pool in hotel: 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 Hotel Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 ~28.78 miles east of Chestertown
  • With a pool!
  • Midscale Suburban hotel
More Photos Photo of Comfort Inn & Suites Pool
From$83
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor : 511 South Central Ave.
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • Midscale Downtown hotel
More Photos Swimming pool at Hyatt Place Baltimore Inner Harbor
From$85
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor in Baltimore
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
625b South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • We have a pool ready for use
  • Affordable Downtown property
More Photos Photo of Hilton Garden Inn Baltimore Inner Harbor Pool
From$110
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore - Baltimore
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
625a South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Has swimming pool
  • 3-star Downtown property
More Photos Pool image of Homewood Suites by Hilton Baltimore
From$80
Very Good 4.5 /5 Read Reviews Call BookMore Details
Residence Inn Dover
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
600 Jefferic Blvd., Dover, DE 19901 ~29.10 miles east of Chestertown
  • Includes a swimming pool
  • Four-star Suburban property
More Photos Swimming pool at Residence Inn Dover
From$125
Average 3.0 /5 Review Score Call BookMore Details
Wyndham Garden Dover Downtown : 561 North Dupont Highway
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
561 North Dupont Highway, Dover, DE 19901 ~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.
  • Mid-scale Downtown hotel
More Photos Photo of Wyndham Garden Dover Downtown Pool
From$71
Average 3.0 /5 Reviews Call BookMore Details
Red Roof Inn Baltimore South Glen Burnie : 6600 Ritchie Highway
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 ~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
  • Low Cost Airport property
More Photos Photo of Red Roof Inn Baltimore South Glen Burnie Pool
From$57
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Easton - Easton
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
8561 Ocean Gateway, Easton, MD 21601 ~29.32 miles south of Chestertown
  • Pool available: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Mid-scale Rural property
More Photos Photo of Holiday Inn Express Easton Pool
From$115
Average 3.0 /5 Hotel Reviews Call BookMore Details
Baymont by Wyndham Easton : 8523 Ocean Gateway
+1-888-878-9982

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8523 Ocean Gateway, Easton, MD 21601 ~29.37 miles south of Chestertown
  • Pool available: 9:00am-9:00pm Outdoor Pool
  • 2 star Rural hotel
More Photos Pool image of Baymont by Wyndham Easton
From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 ~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.
  • 3 star Rural property
More Photos Swimming pool at Comfort Inn & Suites
From$67
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn - Towson
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 ~29.62 miles west of Chestertown
  • Has swimming pool: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Economy Suburban property
More Photos Swimming pool at Comfort Inn
From$56
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Renaissance Baltimore Harborplace Hotel : 202 East Pratt St.
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
202 East Pratt St., Baltimore, MD 21202 ~29.62 miles west of Chestertown
  • Includes a swimming pool
  • Four star Downtown property
More Photos Photo of Renaissance Baltimore Harborplace Hotel Pool
From$144
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor - Baltimore
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
131 East Redwood St., Baltimore, MD 21202 ~29.67 miles west of Chestertown
  • Pool details: 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.
  • Affordable Downtown hotel
More Photos Photo of Hampton Inn & Suites Baltimore Inner Harbor Pool
From$89
Very Good 4.5 /5 Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor : 300 Light St.
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 ~29.71 miles west of Chestertown
  • Includes a swimming pool
  • High end Convention Center property
More Photos Pool image of Hyatt Regency Baltimore Inner Harbor
From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel - Annapolis
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 ~29.76 miles southwest of Chestertown
  • Has swimming pool: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Hours vary.
  • 3 star Suburban hotel
More Photos Photo of Crowne Plaza Annapolis An Ihg Hotel Pool
From$80
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor : 222 Saint Paul Pl
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
222 Saint Paul Pl, Baltimore, MD 21202 ~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.
  • Four-star Downtown property
More Photos Photo of Embassy Suites Baltimore Inner Harbor Pool
From$69
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites in Annapolis
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
Hampton Inn 124, Annapolis, MD 21401 ~29.81 miles southwest of Chestertown
  • Pool in hotel: Seasonal outdoor pool
  • Three Star Highway hotel
More Photos Swimming pool at Hampton Inn & Suites
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel in Towson
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1100 Cromwell Bridge Rd., Towson, MD 21286 ~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.
  • Mid-scale Suburban hotel
More Photos Pool image of Holiday Inn Express Towson Baltimore North An Ihg Hotel
From$69
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis in Annapolis
+1-888-469-4795

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210 Holiday Court, Annapolis, MD 21401 ~30.10 miles southwest of Chestertown
  • Pool details: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Midscale Suburban hotel
More Photos Pool image of Doubletree by Hilton Hotel Annapolis
From$149
Average 3.0 /5 Recent Reviews Call BookMore Details
Best Western Annapolis - Annapolis
+1-888-734-9421

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2520 Riva Rd., Annapolis, MD 21401 ~30.17 miles southwest of Chestertown
  • Has swimming pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 2 star Suburban hotel
More Photos Pool image of Best Western Annapolis
From$84
Average 3.0 /5 Read Reviews Call BookMore Details
Wingate by Wyndham North East
+1-888-841-5292

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39 Elwoods Rd., North East, MD 21901 ~30.29 miles north of Chestertown
  • Pool details: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • Midscale Rural property
More Photos Swimming pool at Wingate by Wyndham North East
From$71
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Annapolis : 124 Womack Dr.
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
124 Womack Dr., Annapolis, MD 21401 ~30.39 miles southwest of Chestertown
  • Pool details: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3-star Suburban hotel
More Photos Photo of Hampton Inn & Suites Annapolis Pool
From$70
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Sonesta Es Suites Annapolis - Annapolis
+1-888-965-8297

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170 Admiral Cochrane Dr., Annapolis, MD 21401 ~30.57 miles southwest of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool
  • Affordable Suburban hotel
More Photos Swimming pool at Sonesta Es Suites Annapolis
From$99
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Galaxy Inn
+1-888-906-6358

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1700 East Lebanon Rd., Dover, DE 19901 ~31.11 miles east of Chestertown
  • Pool available: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • 3 star Suburban property
More Photos Photo of Best Western Galaxy Inn Pool
From$70
Average 3.5 /5 Hotel Reviews Call BookMore Details
Hampton / Home2 Suites Towson - Towson
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
21 West Susquehanna Ave., Towson, MD 21204 ~31.53 miles west of Chestertown
  • Has swimming pool: Indoor Pool 9 AM - 10 PM
  • Mid-scale Downtown hotel
More Photos Pool image of Hampton / Home2 Suites Towson
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Sheraton Baltimore North Hotel - Towson
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
903 Dulaney Valley Rd., Towson, MD 21204 ~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
  • Four-star Suburban hotel
More Photos Swimming pool at Sheraton Baltimore North Hotel
From$103
Very Good 4.0 /5 Read Reviews Call BookMore Details

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