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 : 150 Scheeler Rd.
+1-888-389-4121

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150 Scheeler Rd., Chestertown, MD 21620
  • Pool available: Outdoor seasonal pool. Open 8am-10pm
  • 3 star Suburban hotel
More Photos Photo of Comfort Inn & Suites Chestertown Pool
From$90
Very Good 4.0 /5 Guest Reviews Call BookMore Details
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Holiday Inn Express Annapolis - Kent Island, an IHG Hotel : 1020 Kent Narrows Rd.
+1-888-675-2083

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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
  • Three Star Rural property
More Photos Pool image of Holiday Inn Express Annapolis - Kent Island, an IHG Hotel
From$180
Very Good 4.0 /5 Read 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 in hotel: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Three Star Resort hotel
More Photos Swimming pool at Best Western Kent Narrows Inn
From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md - Aberdeen
+1-800-805-5223

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20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Has swimming pool: **Pool is temporarily closed for extensive maintenance.
  • Two-star Suburban property
More Photos Photo of Home2 Suites by Hilton Baltimore / Aberdeen Md Pool
From$60
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel : 1326 Policy Dr.
+1-888-965-1860

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1326 Policy Dr., Belcamp, MI 21017 ~20.96 miles northwest of Chestertown
  • Has swimming pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban hotel
More Photos Photo of Holiday Inn Belcamp Aberdeen Area An Ihg Hotel Pool
From$80
Average 3.0 /5 Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen - Belcamp
+1-888-788-5576

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1357 Belcamp Rd., Belcamp, MD 21017 ~21.21 miles northwest of Chestertown
  • Includes a pool: Our indoor heated pool is open from 7 am to 10 pm.
  • High-end Rural property
More Photos Swimming pool at Towneplace Suites Edgewood Aberdeen
From$89
Average 3.0 /5 Review Score Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel - Edgewood
+1-888-897-9207

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2118 Emmorton Park Rd., Edgewood, MD 21040 ~21.22 miles northwest of Chestertown
  • Our hotel comes with a pool
  • Three Star Suburban hotel
More Photos Swimming pool at Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
From$119
Very Good 4.0 /5 Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen : 1420 Handlir Dr.
+1-888-311-4278

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1420 Handlir Dr., Bel Air, MD 21015 ~21.27 miles northwest of Chestertown
  • We have a pool
  • Affordable Highway property
More Photos Photo of SpringHill Suites by Marriott Edgewood/Aberdeen Pool
From$106
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD - Bel Air
+1-888-469-4795

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1435 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Pool details: Outdoor Pool, open Memorial Day - Labor Day
  • Three Star Rural hotel
More Photos Pool image of Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South
+1-888-734-9421

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2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.33 miles northwest of Chestertown
  • Pool available: Indoor Pool available 6AM to 10PM
  • Three Star Suburban property
More Photos Swimming pool at Hampton Inn & Suites Edgewood/Aberdeen-South
From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Kent Island Resort
+1-888-841-5292

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500 Kent Manor Dr., Stevensville, MD 21666 ~21.50 miles southwest of Chestertown
  • Includes a pool: Outdoor (seasonal pool)
  • High end Riverfront hotel
More Photos Photo of Kent Island Resort Pool
From$125
Average 3.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen
+1-888-455-5160

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1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.48 miles north of Chestertown
  • Has swimming pool
  • Three Star Suburban property
More Photos Photo of Hilton Garden Inn Aberdeen Pool
From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Aberdeen, an IHG Hotel
+1-888-965-8297

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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.
  • Midscale Highway hotel
More Photos Swimming pool at Holiday Inn Express Aberdeen, an IHG Hotel
From$147
Very Good 4.0 /5 Guest Reviews Call BookMore Details
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Comfort Inn & Suites Aberdeen near APG : 980 Hospitality Way
+1-888-906-6358

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980 Hospitality Way, Aberdeen, MD 21001 ~22.75 miles north of Chestertown
  • Pool details: Seasonal Large Outdoor Pool with picnic tables and grills
  • Mid-scale Highway hotel
More Photos Swimming pool at Comfort Inn & Suites Aberdeen near APG
From$84
Average 3.0 /5 Latest Reviews Call BookMore Details
Courtyard Aberdeen at Ripken Stadium in Aberdeen
+1-888-749-6785

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830 B Long Dr., Aberdeen, MD 21001 ~23.26 miles north of Chestertown
  • Has swimming pool: Indoor Pool
  • Three Star Suburban property
More Photos Swimming pool at Courtyard Aberdeen at Ripken Stadium
From$83
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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Hilton Garden Inn Baltimore/White Marsh : 5015 Campbell Blvd.
+1-888-878-9982

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5015 Campbell Blvd., Baltimore, MD 21236 ~23.76 miles west of Chestertown
  • Pool details: Indoor Pool
  • Three Star Suburban hotel
More Photos Swimming pool at Hilton Garden Inn Baltimore/White Marsh
From$89
Average 3.0 /5 Review Score 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
  • Pool available: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • Three Star Suburban property
More Photos Photo of Hampton Inn Baltimore/White Marsh Pool
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh in Baltimore
+1-888-389-4121

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4980 Mercantile Rd., Baltimore, MD 21236 ~23.86 miles west of Chestertown
  • Pool details: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • Midscale Suburban property
More Photos Photo of Residence Inn by Marriott Baltimore White Marsh Pool
From$109
Average 3.0 /5 Read Reviews Call BookMore Details
Country Inn & Suites by Radisson, Baltimore North, MD : 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
  • Pool available: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • 3-star Suburban hotel
More Photos Photo of Country Inn & Suites by Radisson, Baltimore North, MD Pool
From$80
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh
+1-800-716-8490

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8477 Cordon Way, Baltimore, MD 21236 ~23.93 miles west of Chestertown
  • Pool details: Seasonal Outdoor Pool opens Memorial Day and closed Labor Day
  • Mid-scale Suburban hotel
More Photos Swimming pool at Fairfield Inn & Suites by Marriott White Marsh
From$89
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Exp Stes Middletown : 315 Auto Park Dr.
+1-800-805-5223

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315 Auto Park Dr., Middletown, DE 19709 ~24.19 miles northeast of Chestertown
  • Has swimming pool: Indoor Pool, open year round
  • Affordable 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 - 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
  • Mid-scale Suburban hotel
More Photos Photo of Hampton Inn Middletown Pool
From$94
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Denton Inn : 521 Fleetwood Rd.
+1-888-788-5576

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521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • Our hotel comes with a pool
  • Affordable Highway hotel
More Photos Swimming pool at Best Western Denton Inn
From$67
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 in hotel: Indoor/Heated Pool Lifeguard on duty M-F 5pm - 10pm Sat/Sun 9am -10pm Summer Fri 12p-10p
  • Affordable Suburban hotel
More Photos Swimming pool at Hampton Inn Baltimore Bayview Campus
From$89
Average 3.0 /5 Review Score Call BookMore Details
Best Western Plus Hotel & Conference Center : 5625 O'donnell St.
+1-888-311-4278

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

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1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Pool details: Pool open daily form 8am-10pm.
  • Affordable Suburban hotel
More Photos Swimming pool at Hilton Garden Inn Dover
From$84
Very Good 4.5 /5 Recent Reviews Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-888-734-9421

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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 in hotel: indoor pool. hours vary based upon season
  • Four-star Downtown property
More Photos Photo of The Westin Annapolis Pool
From$139
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-841-5292

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New Reservations: +1-888-841-5292 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
  • Affordable Suburban hotel
More Photos Photo of Comfort Inn & Suites Pool
From$83
Very Good 4.5 /5 Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor in Baltimore
+1-888-455-5160

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511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Pool details: INDOOR POOL
  • Midscale Downtown property
More Photos Pool image of Hyatt Place Baltimore Inner Harbor
From$85
Very Good 4.0 /5 Recent 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
  • Pool in hotel
  • Midscale Downtown hotel
More Photos Pool image of Hilton Garden Inn Baltimore Inner Harbor
From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore Inner Harbor in Baltimore
+1-888-906-6358

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625a South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Includes a swimming pool
  • Midscale Downtown property
More Photos Swimming pool at Homewood Suites by Hilton Baltimore Inner Harbor
From$80
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Baltimore Marriott Waterfront
+1-888-749-6785

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700 Aliceanna St., Baltimore, MD 21202 ~29.10 miles west of Chestertown
  • Our hotel comes with a pool
  • Expensive Downtown property
More Photos Pool image of Baltimore Marriott Waterfront
From$150
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Wyndham Garden Dover Downtown : 561 North Dupont Highway
+1-888-878-9982

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561 North Dupont Highway, Dover, DE 19901 ~29.11 miles east of Chestertown
  • Includes a pool: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • 3-star Downtown hotel
More Photos Pool image of Wyndham Garden Dover Downtown
From$71
Average 3.0 /5 Hotel Reviews Call BookMore Details
Roost Baltimore
+1-888-389-4485

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2460 Terrapin Way, Baltimore, MD 21215 ~29.19 miles west of Chestertown
  • Pool available: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • Expensive hotel
More Photos Swimming pool at Roost Baltimore
From$129
Average 3.0 /5 Latest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie in Glen Burnie
+1-888-389-4121

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6323 Ritchie Highway, Glen Burnie, MD 21061 ~29.21 miles west of Chestertown
  • Pool available: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • Affordable Suburban property
More Photos Pool image of La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
From$75
Average 3.0 /5 Recent Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie
+1-888-675-2083

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6600 Ritchie Highway, Glen Burnie, MD 21061 ~29.23 miles west of Chestertown
  • Pool details: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Cheap Airport hotel
More Photos Pool image of Red Roof Inn Baltimore South - Glen Burnie
From$57
Average 3.0 /5 Reviews Call BookMore Details
Holiday Inn Express Easton in Easton
+1-800-716-8490

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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 hotel
More Photos Swimming pool at Holiday Inn Express Easton
From$115
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 ~29.39 miles north of Chestertown
  • Has swimming pool: 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 property
More Photos Photo of Comfort Inn & Suites Pool
From$67
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn : 8801 Loch Raven Blvd.
+1-888-965-1860

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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.
  • 2 star Suburban property
More Photos Pool image of Comfort Inn
From$56
Very Good 4.0 /5 Latest Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore
+1-888-788-5576

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550 Light St., Baltimore, MD 21202 ~29.64 miles west of Chestertown
  • Has swimming pool: 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 property
More Photos Pool image of The Royal Sonesta Harbor Court Baltimore
From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor : 131 East Redwood St.
+1-888-897-9207

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131 East Redwood St., Baltimore, MD 21202 ~29.67 miles west of Chestertown
  • Pool in hotel: 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 Photo of Hampton Inn & Suites Baltimore Inner Harbor Pool
From$89
Very Good 4.5 /5 Read Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor : 300 Light St.
+1-888-311-4278

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300 Light St., Baltimore, MD 21202 ~29.71 miles west of Chestertown
  • Has a pool!
  • 4-star Convention Center hotel
More Photos Photo of Hyatt Regency Baltimore Inner Harbor Pool
From$125
Average 3.0 /5 Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel - Annapolis
+1-888-469-4795

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173 Jennifer Rd., Annapolis, MD 21401 ~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. Also large whirlpool tht seats 6. Hours vary.
  • Three Star Suburban hotel
More Photos Photo of Crowne Plaza Annapolis An Ihg Hotel Pool
From$80
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Dover, DE
+1-888-734-9421

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222 South Dupont Highway, Dover, DE 19901 ~29.76 miles east of Chestertown
  • Has swimming pool: 6am - 10pm
  • 2 star Downtown property
More Photos Pool image of Home2 Suites by Hilton Dover, DE
From$99
Very Good 4.0 /5 Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor - Baltimore
+1-888-841-5292

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222 Saint Paul Pl, Baltimore, MD 21202 ~29.79 miles west of Chestertown
  • Pool available: 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.
  • High-end Downtown hotel
More Photos Photo of Embassy Suites Baltimore Inner Harbor Pool
From$69
Average 3.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites - Annapolis
+1-888-455-5160

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Hampton Inn 124, Annapolis, MD 21401 ~29.81 miles southwest of Chestertown
  • Pool in hotel: Seasonal outdoor pool
  • Midscale Highway property
More Photos Pool image of Hampton Inn & Suites
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Radisson Hotel Baltimore Downtown Inner Harbor in Baltimore
+1-888-965-8297

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101 West Fayette St., Baltimore, MD 21201 ~29.90 miles west of Chestertown
  • Has swimming pool: Come experience our seasonal Rooftop Outdoor Pool opens Memorial Day to Labor Day.
  • 3 star Downtown property
More Photos Photo of Radisson Hotel Baltimore Downtown Inner Harbor Pool
From$87
Poor 2.0 /5 Read Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor
+1-888-906-6358

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100 Hopkins Pl, Baltimore, MD 21201 ~29.93 miles west of Chestertown
  • Pool available: Outdoor pool (seasonal)
  • Midscale Downtown hotel
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
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
1100 Cromwell Bridge Rd., Towson, MD 21286 ~30.06 miles west of Chestertown
  • Pool in hotel: 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.
  • Midscale Suburban property
More Photos Swimming pool at Holiday Inn Express Towson Baltimore North An Ihg Hotel
From$69
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Baltimore Inner Harbor
+1-888-878-9982

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401 West Pratt St., Baltimore, MD 21201 ~30.07 miles west of Chestertown
  • Pool details: The Hilton Baltimore has a 30ft two lane track pool.
  • 4-star Downtown property
More Photos Pool image of Hilton Baltimore Inner Harbor
From$99
Very Good 4.0 /5 Hotel Reviews Call BookMore Details

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