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

Comfort Inn & Suites Chestertown in Chestertown
+1-888-389-4121

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150 Scheeler Rd., Chestertown, MD 21620
  • Pool available: Outdoor seasonal pool. Open 8am-10pm
  • Mid-scale Suburban property
More Photos Photo of Comfort Inn & Suites Chestertown Pool
From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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Holiday Inn Express Annapolis - Kent Island, an IHG Hotel 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
  • Has swimming pool: Outdoor pool open from Memorial day to labor day 9am-9pm
  • 3-star Rural property
More Photos Pool image of Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
From$180
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Kent Narrows Inn - Grasonville
+1-800-716-8490

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3101 Main St., Grasonville, MD 21638 ~19.04 miles southwest of Chestertown
  • Pool available: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Midscale Resort hotel
More Photos Swimming pool at Best Western Kent Narrows Inn
From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Kent Island
+1-800-805-5223

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3206 Main St., Grasonville, MD 21638 ~19.08 miles southwest of Chestertown
  • Includes a pool: Indoor pool open daily 5 AM-11PM
  • Three Star Riverfront hotel
More Photos Pool image of Hilton Garden Inn Kent Island
From$121
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen, MD
+1-888-965-1860

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20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Pool details: **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 Read Reviews Call BookMore Details
Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel - Belcamp
+1-888-788-5576

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1326 Policy Dr., Belcamp, MI 21017 ~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban property
More Photos Swimming pool at Holiday Inn Belcamp - Aberdeen Area, an IHG Hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Towneplace Suites by Marriott in Belcamp
+1-888-897-9207

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1357 Belcamp Rd., Belcamp, MD 21017 ~21.21 miles northwest of Chestertown
  • Includes a pool: Our indoor pool opens from 7 am to 10 pm.
  • High-end Rural property
More Photos Swimming pool at Towneplace Suites by Marriott
From$89
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
+1-888-311-4278

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2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.22 miles northwest of Chestertown
  • We have a pool
  • 3 star Suburban property
More Photos Swimming pool at Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
From$119
Very Good 4.0 /5 Hotel 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
  • Includes a pool: Indoor Pool available 6AM to 10PM
  • 3-star Suburban property
More Photos Pool image of Hampton Inn & Suites Edgewood/Aberdeen-South
From$95
Very Good 4.0 /5 Read Reviews Call BookMore Details
Kent Island Resort
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
500 Kent Manor Dr., Stevensville, MD 21666 ~21.50 miles southwest of Chestertown
  • Pool in hotel: Outdoor (seasonal pool)
  • Expensive Riverfront hotel
More Photos Swimming pool at Kent Island Resort
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen
+1-888-841-5292

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1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.48 miles north of Chestertown
  • Includes a pool
  • Affordable Suburban property
More Photos Swimming pool at Hilton Garden Inn Aberdeen
From$110
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Aberdeen : 1007 Beards Hill Rd.
+1-888-455-5160

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1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • Pool available: 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 Photo of Holiday Inn Express Aberdeen Pool
From$147
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen-APG - Aberdeen
+1-888-965-8297

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793 West Bel Air Ave., Aberdeen, MD 21001 ~22.62 miles north of Chestertown
  • We have a pool
  • Low priced Rural hotel
More Photos Photo of La Quinta Inn & Suites by Wyndham Aberdeen-APG Pool
From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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Hampton Inn & Suites Baltimore/Aberdeen
+1-888-906-6358

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795 West Bel Air Ave., Aberdeen, MD 21001 ~22.63 miles north of Chestertown
  • Pool in hotel: Indoor pool
  • Low priced Highway property
More Photos Pool image of Hampton Inn & Suites Baltimore/Aberdeen
From$89
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Comfort Inn Suites
+1-888-749-6785

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980 Hospitality Way, Aberdeen, MD 21001 ~22.75 miles north of Chestertown
  • Includes a pool: Seasonal Large Outdoor Pool with picnic tables and grills
  • Midscale Highway property
More Photos Pool image of Comfort Inn Suites
From$84
Average 3.0 /5 Recent Reviews Call BookMore Details
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Hilton Garden Inn Baltimore/White Marsh
+1-888-878-9982

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5015 Campbell Blvd., Baltimore, MD 21236 ~23.76 miles west of Chestertown
  • Includes a pool: Indoor Pool
  • 3-star Suburban property
More Photos Swimming pool at Hilton Garden Inn Baltimore/White Marsh
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh
+1-888-389-4485

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8225 Town Center Dr., Nottingham, MD 21236 ~23.79 miles west of Chestertown
  • Includes a pool: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • 3 star Suburban property
More Photos Pool image of Hampton Inn Baltimore/White Marsh
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh
+1-888-389-4121

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4980 Mercantile Rd., White Marsh, MD 21236 ~23.86 miles west of Chestertown
  • Has swimming pool: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • Three Star Suburban hotel
More Photos Swimming pool at Residence Inn by Marriott Baltimore White Marsh
From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites Baltimore North / White Marsh : 8825 Yellow Brick Rd.
+1-888-675-2083

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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
  • Mid-scale Suburban property
More Photos Photo of Country Inn & Suites Baltimore North / White Marsh Pool
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh : 8477 Cordon Way
+1-800-716-8490

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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 and closed Labor Day
  • Mid-scale Suburban property
More Photos Pool image of Fairfield Inn & Suites by Marriott White Marsh
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown
+1-800-805-5223

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315 Auto Park Dr., Middletown, DE 19709 ~24.19 miles northeast of Chestertown
  • Pool details: Indoor Pool, open year round
  • 3-star Suburban property
More Photos Photo of Holiday Inn Exp Stes Middletown Pool
From$70
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn Middletown
+1-888-965-1860

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117 Sandhill Dr., Middletown, DE 19709 ~24.53 miles northeast of Chestertown
  • Includes a swimming pool
  • Midscale Suburban hotel
More Photos Pool image of Hampton Inn Middletown
From$94
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Denton Inn - Denton
+1-888-788-5576

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521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • Pool in hotel
  • Midscale Highway hotel
More Photos Swimming pool at Best Western Denton Inn
From$68
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Baltimore Bayview Campus in Baltimore
+1-888-897-9207

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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
  • Mid-scale Suburban hotel
More Photos Photo of Hampton Inn Baltimore Bayview Campus Pool
From$89
Average 3.0 /5 Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center
+1-888-311-4278

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5625 O'donnell St., Baltimore, MD 21224 ~26.13 miles west of Chestertown
  • Pool details: Indoor heated pool Open 10 am - 10 pm, weekly.
  • 3-star Highway hotel
More Photos Photo of Best Western Plus Hotel & Conference Center Pool
From$72
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Includes a pool: **COVID may have affected some hotel amenities, please inquire with your group/event coordinator**Indoor pool and hot tub open daily 6am-10pm
  • Mid-scale Suburban hotel
More Photos Photo of Hilton Garden Inn Dover Pool
From$84
Very Good 4.5 /5 Latest Reviews Call BookMore Details
The Westin Annapolis in Annapolis
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 ~28.40 miles southwest of Chestertown
  • Pool available: indoor pool. hours vary based upon season
  • Four-star Downtown property
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
+1-888-841-5292

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764 Dover Leipsic Rd., Dover, DE 19901 ~28.78 miles east of Chestertown
  • Includes a pool
  • Mid-scale Suburban property
More Photos Photo of Comfort Inn & Suites Pool
From$83
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Pool details: INDOOR POOL
  • Mid-scale Downtown hotel
More Photos Swimming pool at Hyatt Place Baltimore Inner Harbor
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor
+1-888-965-8297

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625 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 Recent Reviews Call BookMore Details
Wyndham Garden Dover Downtown - Dover
+1-888-906-6358

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561 North Dupont Highway, Dover, DE 19901 ~29.11 miles east of Chestertown
  • Pool details: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • Midscale Downtown property
More Photos Photo of Wyndham Garden Dover Downtown Pool
From$71
Average 3.0 /5 Guest Reviews Call BookMore Details
Roost Baltimore - Baltimore
+1-888-749-6785

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2460 Terrapin Way, Baltimore, MD 21215 ~29.19 miles west of Chestertown
  • Has swimming pool: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • 4 star property
More Photos Photo of Roost Baltimore Pool
From$129
Average 3.0 /5 Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie
+1-888-878-9982

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6600 Ritchie Highway, Glen Burnie, MD 21061 ~29.23 miles west of Chestertown
  • Includes a pool: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Economical Airport hotel
More Photos Pool image of Red Roof Inn Baltimore South - Glen Burnie
From$57
Average 3.0 /5 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
+1-888-389-4485

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6323 Ritchie Highway, Glen Burnie, MD 21061 ~29.24 miles west of Chestertown
  • Pool available: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3-star Suburban property
More Photos Swimming pool at La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
From$69
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-389-4121

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8561 Ocean Gateway, Easton, MD 21601 ~29.32 miles south of Chestertown
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Midscale Rural property
More Photos Swimming pool at Holiday Inn Express Easton
From$115
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites - North East
+1-888-675-2083

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1 Center Dr., North East, MD 21901 ~29.39 miles north of Chestertown
  • Includes a pool: 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 Hotel Reviews Call BookMore Details
Comfort Inn
+1-800-716-8490

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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.
  • Low Cost Suburban hotel
More Photos Pool image of Comfort Inn
From$56
Very Good 4.0 /5 Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore - Baltimore
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21202 ~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
  • Four star Downtown hotel
More Photos Pool image of The Royal Sonesta Harbor Court Baltimore
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor - Baltimore
+1-888-965-1860

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131 East Redwood St., Baltimore, MD 21202 ~29.67 miles west of Chestertown
  • Pool available: 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 property
More Photos Swimming pool at Hampton Inn & Suites Baltimore Inner Harbor
From$89
Very Good 4.5 /5 Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel in Annapolis
+1-888-788-5576

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New Reservations: +1-888-788-5576 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. Also large whirlpool tht seats 6. Hours vary.
  • Midscale Suburban hotel
More Photos Photo of Crowne Plaza Annapolis An Ihg Hotel Pool
From$80
Very Good 4.0 /5 Reviews Call BookMore Details
Home2 Suites by Hilton Dover, DE
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 ~29.76 miles east of Chestertown
  • Has swimming pool: 6am - 10pm
  • Two star Downtown hotel
More Photos Pool image of Home2 Suites by Hilton Dover, DE
From$99
Very Good 4.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor : 100 Hopkins Pl
+1-888-311-4278

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100 Hopkins Pl, Baltimore, MD 21201 ~29.93 miles west of Chestertown
  • Includes a pool: Outdoor pool (seasonal)
  • Three Star Downtown hotel
More Photos Swimming pool at Days Inn by Wyndham Baltimore Inner Harbor
From$73
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Inner Harbor - Baltimore
+1-888-469-4795

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301 West Lombard St., Baltimore, MD 21201 ~30.05 miles west of Chestertown
  • Pool in hotel: ***** Closed for renovations through May of 2019. MONDAY – THURSDAY 6:30 AM-10:00 AM 4:30 PM-10:00 PM FRIDAY 6:30 AM-10 PM SATURDAY - SUNDAY 8:00 AM - 10:00 PM Largest Indoor Pool in Baltimore. 50' x 25'
  • 3 star Downtown property
More Photos Swimming pool at Holiday Inn Inner Harbor
From$70
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-734-9421

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1100 Cromwell Bridge Rd., Towson, MD 21286 ~30.06 miles west of Chestertown
  • Has swimming 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.
  • Three Star Suburban hotel
More Photos Photo of Holiday Inn Express Towson Baltimore North An Ihg Hotel Pool
From$69
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Annapolis
+1-888-841-5292

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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.
  • Low Cost Suburban property
More Photos Swimming pool at Best Western Annapolis
From$84
Average 3.0 /5 Reviews Call BookMore Details
Best Western Chesapeake Bay North Inn
+1-888-455-5160

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39 Elwoods Rd., North East, MD 21901 ~30.29 miles north of Chestertown
  • Includes a pool: Indoor pool and hot tub currently closed.
  • Affordable Rural property
More Photos Photo of Best Western Chesapeake Bay North Inn Pool
From$71
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Annapolis - Annapolis
+1-888-965-8297

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124 Womack Dr., Annapolis, MD 21401 ~30.39 miles southwest of Chestertown
  • Pool in hotel: 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 Latest Reviews Call BookMore Details
Courtyard by Marriott Annapolis
+1-888-906-6358

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2559 Riva Rd., Annapolis, MD 21401 ~30.53 miles southwest of Chestertown
  • We have a pool ready for use
  • Affordable Downtown hotel
More Photos Photo of Courtyard by Marriott Annapolis Pool
From$79
Very Good 4.0 /5 Review Score Call BookMore Details
Sonesta Es Suites Annapolis in Annapolis
+1-888-749-6785

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170 Admiral Cochrane Dr., Annapolis, MD 21401 ~30.57 miles southwest of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool
  • 4 star Suburban property
More Photos Pool image of Sonesta Es Suites Annapolis
From$99
Very Good 4.0 /5 Reviews Call BookMore Details
Springhill Suites by Marriott Annapolis
+1-888-878-9982

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189 Admiral Cochrane Dr., Annapolis, MD 21401 ~30.57 miles southwest of Chestertown
  • Pool available: Indoor Swimming Pool with Whirlpool Spa Tub and Outdoor Patio Area Daily from 10:00am - 10:00pm Social Distancing required. Sign up for a 45 minute pool session at the Front Desk. Groups can book a time slot ahead of time.
  • 3 star Suburban property
More Photos Photo of Springhill Suites by Marriott Annapolis Pool
From$82
Average 3.0 /5 Guest Reviews Call BookMore Details

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