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
+1-888-389-4121

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101 Vfw Ave., Grasonville, MD 21638 ~18.54 miles southwest of Chestertown
  • Has a pool!
  • 2-star Resort hotel
More Photos Swimming pool at Quality Inn
From$74
Very Good 4.0 /5 Latest Reviews Call BookMore Details
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Holiday Inn Express Annapolis East-Kent Island by IHG in Grasonville
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Pool in hotel: Outdoor pool open from Memorial day to labor day 9am-9pm
  • 3 star Rural hotel
More Photos Pool image of Holiday Inn Express Annapolis East-Kent Island by IHG
From$180
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Kent Narrows Inn in Grasonville
+1-800-716-8490

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3101 Main St., Grasonville, MD 21638 ~19.04 miles southwest of Chestertown
  • Includes a pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • 3 star Resort property
More Photos Pool image of Best Western Kent Narrows Inn
From$80
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel - 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
  • Pool in hotel: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Midscale Suburban property
More Photos Photo of Holiday Inn Belcamp Aberdeen Area An Ihg Hotel Pool
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
  • With a pool!
  • 3 star Suburban hotel
More Photos Photo of Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area Pool
From$54
Average 3.0 /5 Review Score Call BookMore Details
Towneplace Suites Edgewood Aberdeen : 1357 Belcamp Rd.
+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.
  • 3 star Rural hotel
More Photos Swimming pool at Towneplace Suites Edgewood Aberdeen
From$89
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South : 2110 Emmorton Park Rd.
+1-888-897-9207

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2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.33 miles northwest of Chestertown
  • Pool in hotel: Indoor Pool available 6AM to 10PM
  • Three Star Suburban hotel
More Photos Photo of Hampton Inn & Suites Edgewood/Aberdeen-South Pool
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG - Aberdeen
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • Pool in hotel: 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.
  • Midscale Highway hotel
More Photos Swimming pool at Holiday Inn Express Aberdeen by IHG
From$147
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen : 783 West Bel Air Ave.
+1-888-469-4795

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783 West Bel Air Ave., Aberdeen, MD 21001 ~22.53 miles north of Chestertown
  • Pool available: We have Outdoor Pool. Opens from Memorial day to labor day
  • Two star Highway property
More Photos Photo of Days Inn by Wyndham Aberdeen Pool
From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg
+1-888-734-9421

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980 Hospitality Way, Aberdeen, MD 21001 ~22.75 miles north of Chestertown
  • Has swimming pool: Seasonal Large Outdoor Pool with picnic tables and grills
  • Three Star Highway property
More Photos Photo of Comfort Inn & Suites Aberdeen Near Apg Pool
From$84
Average 3.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Baltimore / White Marsh - Baltimore
+1-888-841-5292

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5015 Campbell Blvd., Baltimore, MD 21236 ~23.76 miles west of Chestertown
  • Pool available: Indoor Pool
  • Affordable Suburban property
More Photos Swimming pool at Hilton Garden Inn Baltimore / White Marsh
From$89
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Baltimore / White Marsh
+1-888-455-5160

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8225 Town Center Dr., Nottingham, MD 21236 ~23.79 miles west of Chestertown
  • Pool available: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • Affordable Suburban hotel
More Photos Swimming pool at Hampton Inn Baltimore / White Marsh
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh : 4980 Mercantile Rd.
+1-888-965-8297

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4980 Mercantile Rd., Baltimore, MD 21236 ~23.86 miles west of Chestertown
  • Includes a pool: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • 3-star Suburban hotel
More Photos Pool image of Residence Inn by Marriott Baltimore White Marsh
From$109
Average 3.0 /5 Hotel Reviews Call BookMore Details
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Fairfield Inn & Suites by Marriott White Marsh : 8477 Cordon Way
+1-888-906-6358

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8477 Cordon Way, Baltimore, MD 21236 ~23.93 miles west of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool opens Memorial Day and closed Labor Day
  • Three Star Suburban property
More Photos Photo of Fairfield Inn & Suites by Marriott White Marsh Pool
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown
+1-888-749-6785

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315 Auto Park Dr., Middletown, DE 19709 ~24.19 miles northeast of Chestertown
  • Pool in hotel: Indoor Pool, open year round
  • 3 star Suburban property
More Photos Pool image of Holiday Inn Exp Stes Middletown
From$70
Very Good 4.5 /5 Review Score Call BookMore Details
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Best Western Denton Inn - Denton
+1-888-878-9982

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521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • Our hotel comes with a pool
  • 3 star Highway hotel
More Photos Swimming pool at Best Western Denton Inn
From$68
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Plus Hotel & Conference Center : 5625 O'donnell St.
+1-888-389-4485

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5625 O'donnell St., Baltimore, MD 21224 ~26.13 miles west of Chestertown
  • Includes a pool: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Three Star Highway property
More Photos Photo of Best Western Plus Hotel & Conference Center Pool
From$72
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Dover : 1706 North Dupont Highway
+1-888-389-4121

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1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Has swimming pool: Pool open daily form 8am-10pm.
  • Three Star Suburban property
More Photos Pool image of Hilton Garden Inn Dover
From$84
Very Good 4.5 /5 Review Score Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-888-675-2083

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100 Westgate Cir, Annapolis, MD 21401 ~28.40 miles southwest of Chestertown
  • Includes a pool: indoor pool. hours vary based upon season
  • Expensive Downtown hotel
More Photos Pool image of The Westin Annapolis
From$139
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites in Dover
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 ~28.78 miles east of Chestertown
  • Our hotel comes with a pool
  • Three Star Suburban hotel
More Photos Pool image of Comfort Inn & Suites
From$83
Very Good 4.5 /5 Review Score Call BookMore Details
Hyatt Place Baltimore Inner Harbor - Baltimore
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Pool available: INDOOR POOL
  • Affordable Downtown property
More Photos Pool image of Hyatt Place Baltimore Inner Harbor
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor
+1-888-965-1860

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625b South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Includes a pool
  • 3-star Downtown property
More Photos Photo of Hilton Garden Inn Baltimore Inner Harbor Pool
From$110
Very Good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore - Baltimore
+1-888-788-5576

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625a South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Has swimming pool
  • Midscale Downtown hotel
More Photos Swimming pool at Homewood Suites by Hilton Baltimore
From$80
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-897-9207

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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.
  • Midscale Downtown property
More Photos Pool image of Wyndham Garden Dover Downtown
From$71
Average 3.0 /5 Hotel Reviews Call BookMore Details
Roost Baltimore in Baltimore
+1-888-311-4278

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2460 Terrapin Way, Baltimore, MD 21215 ~29.19 miles west of Chestertown
  • Pool in hotel: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • High end hotel
More Photos Swimming pool at Roost Baltimore
From$129
Average 3.0 /5 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
6323 Ritchie Highway, Glen Burnie, MD 21061 ~29.21 miles west of Chestertown
  • Has swimming pool: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • Midscale Suburban property
More Photos Swimming pool at La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 ~29.23 miles west of Chestertown
  • Pool in hotel: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • 2-star Airport hotel
More Photos Swimming pool at Red Roof Inn Baltimore South - Glen Burnie
From$57
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-841-5292

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New Reservations: +1-888-841-5292 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
  • Affordable Rural hotel
More Photos Photo of Holiday Inn Express Easton Pool
From$115
Average 3.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 ~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.
  • Three Star Rural hotel
More Photos Photo of Comfort Inn & Suites Pool
From$67
Average 3.0 /5 Latest Reviews Call BookMore Details
Tremont Plaza Hotel - Baltimore
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
222 St. Paul Place, Baltimore, MD 21202 ~29.52 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.
  • Midscale Downtown hotel
More Photos Swimming pool at Tremont Plaza Hotel
From$89
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn : 8801 Loch Raven Blvd.
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 ~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$56
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore in Baltimore
+1-888-749-6785

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550 Light St., Baltimore, MD 21202 ~29.64 miles west of Chestertown
  • Pool available: 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 Swimming pool at The Royal Sonesta Harbor Court Baltimore
From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor : 131 East Redwood St.
+1-888-878-9982

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New Reservations: +1-888-878-9982 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.
  • 3 star Downtown hotel
More Photos Pool image of Hampton Inn & Suites Baltimore Inner Harbor
From$89
Very Good 4.5 /5 Review Score Call BookMore Details
Hyatt Regency Baltimore Inner Harbor in Baltimore
+1-888-389-4485

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300 Light St., Baltimore, MD 21202 ~29.71 miles west of Chestertown
  • We have a pool ready for use
  • High-end Convention Center property
More Photos Photo of Hyatt Regency Baltimore Inner Harbor Pool
From$125
Average 3.0 /5 Hotel Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-888-389-4121

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173 Jennifer Rd., Annapolis, MD 21401 ~29.76 miles southwest of Chestertown
  • Pool available: 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 Swimming pool at Crowne Plaza Annapolis An Ihg Hotel
From$80
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Dover De - Dover
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 ~29.76 miles east of Chestertown
  • Pool in hotel: 6am - 10pm
  • Two-star Downtown hotel
More Photos Photo of Home2 Suites by Hilton Dover De Pool
From$99
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites - Annapolis
+1-800-716-8490

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Hampton Inn 124, Annapolis, MD 21401 ~29.81 miles southwest of Chestertown
  • Includes a pool: Seasonal outdoor pool
  • Three Star Highway hotel
More Photos Pool image of Hampton Inn & Suites
From$80
Average 3.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor - Baltimore
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
100 Hopkins Pl, Baltimore, MD 21201 ~29.93 miles west of Chestertown
  • Pool available: Outdoor pool (seasonal)
  • Affordable Downtown property
More Photos Photo of Days Inn by Wyndham Baltimore Inner Harbor Pool
From$73
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel in Towson
+1-888-965-1860

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1100 Cromwell Bridge Rd., Towson, MD 21286 ~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.
  • 3 star Suburban hotel
More Photos Photo of Holiday Inn Express Towson Baltimore North An Ihg Hotel Pool
From$69
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis in Annapolis
+1-888-788-5576

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210 Holiday Court, Annapolis, MD 21401 ~30.10 miles southwest of Chestertown
  • Pool in hotel: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Mid-scale Suburban hotel
More Photos Photo of Doubletree by Hilton Hotel Annapolis Pool
From$149
Average 3.0 /5 Latest Reviews Call BookMore Details
Best Western Annapolis in Annapolis
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
2520 Riva Rd., Annapolis, MD 21401 ~30.17 miles southwest of Chestertown
  • Pool in hotel: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Low Cost Suburban property
More Photos Pool image of Best Western Annapolis
From$84
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Chesapeake Bay North Inn
+1-888-311-4278

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39 Elwoods Rd., North East, MD 21901 ~30.29 miles north of Chestertown
  • Pool in hotel: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • Three Star Rural property
More Photos Swimming pool at Best Western Chesapeake Bay North Inn
From$71
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Annapolis in Annapolis
+1-888-469-4795

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124 Womack Dr., Annapolis, MD 21401 ~30.39 miles southwest of Chestertown
  • Pool available: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3 star Suburban property
More Photos Swimming pool at Hampton Inn & Suites Annapolis
From$70
Very Good 4.0 /5 Read Reviews Call BookMore Details
Sonesta Es Suites Annapolis - Annapolis
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
170 Admiral Cochrane Dr., Annapolis, MD 21401 ~30.57 miles southwest of Chestertown
  • Includes a pool: Seasonal Outdoor Pool
  • High end Suburban property
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 in Dover
+1-888-841-5292

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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.
  • Affordable Suburban hotel
More Photos Swimming pool at Best Western Galaxy Inn
From$70
Average 3.5 /5 Review Score Call BookMore Details
Hampton / Home2 Suites Towson
+1-888-455-5160

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21 West Susquehanna Ave., Towson, MD 21204 ~31.53 miles west of Chestertown
  • Has swimming pool: Indoor Pool 9 AM - 10 PM
  • Three Star Downtown property
More Photos Swimming pool at Hampton / Home2 Suites Towson
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Sheraton Baltimore North in Towson
+1-888-965-8297

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903 Dulaney Valley Rd., Towson, MD 21204 ~31.54 miles west of Chestertown
  • Has swimming pool: Hotel has an indoor pool. Pool is open from 7am -10pm.
  • Three Star Suburban hotel
More Photos Swimming pool at Sheraton Baltimore North
From$80
Average 3.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Easton in Easton
+1-888-906-6358

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7018 Ocean Gateway, Easton, MD 21601 ~32.19 miles south of Chestertown
  • Includes a pool: out door swimming pool
  • 3-star property
More Photos hotel room
From$80
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn Elkton
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2 Warner Rd., Elkton, MD 21921 ~32.48 miles northeast of Chestertown
  • Includes a pool: 9am- 10pm
  • Midscale Highway hotel
More Photos Swimming pool at Hampton Inn Elkton
From$119
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Delta Marriott Baltimore North
+1-888-878-9982

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5100 Falls Rd., Baltimore, MD 21210 ~32.56 miles west of Chestertown
  • Has swimming pool: Large Outdoor Seasonal Pool staffed with lifeguard, open 10 am - dusk daily, Memorial Day to Labor Day.
  • Midscale Suburban property
More Photos Pool image of Delta Marriott Baltimore North
From$74
Very Good 4.0 /5 Reviews Call BookMore Details

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