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

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

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150 Scheeler Rd., Chestertown, MD 21620 +1-888-389-4121
  • Pool in hotel: Outdoor seasonal pool. Open 8am-10pm
  • 3 star Suburban hotel
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From$90
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Annapolis - Kent Island, an IHG Hotel - 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 +1-888-675-2083 ~18.94 miles southwest of Chestertown
  • Has swimming pool: Outdoor pool open from Memorial day to labor day 9am-9pm
  • Midscale Rural hotel
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From$180
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Kent Narrows Inn : 3101 Main St.
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
3101 Main St., Grasonville, MD 21638 +1-800-716-8490 ~19.04 miles southwest of Chestertown
  • Includes a pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Three Star Resort hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Kent Island
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
3206 Main St., Grasonville, MD 21638 +1-800-805-5223 ~19.08 miles southwest of Chestertown
  • Pool available: Indoor pool open daily 5 AM-11PM
  • Affordable Riverfront property
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From$121
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
+1-888-965-1860

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1326 Policy Dr., Belcamp, MI 21017 +1-888-965-1860 ~20.96 miles northwest of Chestertown
  • Pool in hotel: Indoor Heated Pool. Open from 9am - 10pm daily.
  • 3 star Suburban hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites by Marriott
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1357 Belcamp Rd., Belcamp, MD 21017 +1-888-788-5576 ~21.21 miles northwest of Chestertown
  • Pool in hotel: Our indoor pool opens from 7 am to 10 pm.
  • Four star Rural property
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From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
+1-888-897-9207

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2118 Emmorton Park Rd., Edgewood, MD 21040 +1-888-897-9207 ~21.22 miles northwest of Chestertown
  • We have a pool
  • Three Star Suburban hotel
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From$119
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Springhill Suites by Marriott Edgewood / Aberdeen
+1-888-311-4278

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1420 Handlir Dr., Bel Air, MD 21015 +1-888-311-4278 ~21.27 miles northwest of Chestertown
  • Has a pool!
  • Affordable Highway hotel
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From$106
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South in Edgewood
+1-888-469-4795

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2110 Emmorton Park Rd., Edgewood, MD 21040 +1-888-469-4795 ~21.33 miles northwest of Chestertown
  • Pool in hotel: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban property
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From$95
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Kent Island Resort - Stevensville
+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 +1-888-734-9421 ~21.50 miles southwest of Chestertown
  • Pool details: Outdoor (seasonal pool)
  • 4-star Riverfront property
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From$125
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Aberdeen
+1-888-841-5292

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1050 Beards Hill Rd., Aberdeen, MD 21001 +1-888-841-5292 ~22.48 miles north of Chestertown
  • Includes a pool
  • Mid-scale Suburban property
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From$110
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Aberdeen
+1-888-455-5160

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1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-455-5160 ~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.
  • Mid-scale Highway property
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From$147
Very Good 4.0 /5 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 +1-888-965-8297 ~22.62 miles north of Chestertown
  • Our hotel comes with a pool
  • Two-star Rural hotel
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From$109
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen in Aberdeen
+1-888-906-6358

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795 West Bel Air Ave., Aberdeen, MD 21001 +1-888-906-6358 ~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • 2-star Highway hotel
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From$89
Very Good 4.5 /5 Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen near APG in Aberdeen
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
980 Hospitality Way, Aberdeen, MD 21001 +1-888-749-6785 ~22.75 miles north of Chestertown
  • Has swimming pool: Seasonal Large Outdoor Pool with picnic tables and grills
  • Midscale Highway hotel
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From$84
Average 3.0 /5 Reviews Call BookMore Details
Courtyard Aberdeen at Ripken Stadium : 830 B Long Dr.
+1-888-878-9982

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830 B Long Dr., Aberdeen, MD 21001 +1-888-878-9982 ~23.26 miles north of Chestertown
  • Pool available: Indoor Pool
  • 3 star Suburban property
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From$83
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Baltimore / White Marsh
+1-888-389-4485

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5015 Campbell Blvd., Baltimore, MD 21236 +1-888-389-4485 ~23.76 miles west of Chestertown
  • Pool available: Indoor Pool
  • Midscale Suburban property
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From$89
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Baltimore / White Marsh : 8225 Town Center Dr.
+1-888-389-4121

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8225 Town Center Dr., Nottingham, MD 21236 +1-888-389-4121 ~23.79 miles west of Chestertown
  • Pool in hotel: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • Affordable Suburban hotel
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From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh - Baltimore
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
4980 Mercantile Rd., Baltimore, MD 21236 +1-888-675-2083 ~23.86 miles west of Chestertown
  • Pool details: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • Midscale Suburban property
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From$109
Average 3.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites Baltimore North / White Marsh
+1-800-716-8490

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8825 Yellow Brick Rd., Rosedale, MD 21237 +1-800-716-8490 ~23.90 miles west of Chestertown
  • Includes a pool: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Three Star Suburban hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh - Baltimore
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
8477 Cordon Way, Baltimore, MD 21236 +1-800-805-5223 ~23.93 miles west of Chestertown
  • Pool available: Seasonal Outdoor Pool opens Memorial Day and closed Labor Day
  • Mid-scale Suburban hotel
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From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown - Middletown
+1-888-965-1860

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315 Auto Park Dr., Middletown, DE 19709 +1-888-965-1860 ~24.19 miles northeast of Chestertown
  • Pool details: Indoor Pool, open year round
  • Mid-scale Suburban property
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From$70
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Hampton Inn Middletown : 117 Sandhill Dr.
+1-888-788-5576

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117 Sandhill Dr., Middletown, DE 19709 +1-888-788-5576 ~24.53 miles northeast of Chestertown
  • Includes a swimming pool
  • 3 star Suburban property
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From$94
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Denton Inn
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
521 Fleetwood Rd., Denton, MD 21629 +1-888-897-9207 ~25.35 miles southeast of Chestertown
  • Our hotel comes with a pool
  • 3-star Highway property
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From$68
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hampton Inn Baltimore Bayview Campus
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
6571 Eastern Ave., Baltimore, MD 21224 +1-888-311-4278 ~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
  • Midscale Suburban hotel
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From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center
+1-888-469-4795

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5625 O'donnell St., Baltimore, MD 21224 +1-888-469-4795 ~26.13 miles west of Chestertown
  • Pool available: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Mid-scale Highway property
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From$72
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Dover
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 +1-888-734-9421 ~27.40 miles east of Chestertown
  • Pool details: **COVID may have affected some hotel amenities, please inquire with your group/event coordinator**Indoor pool and hot tub open daily 6am-10pm
  • Midscale Suburban property
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From$84
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 +1-888-841-5292 ~28.40 miles southwest of Chestertown
  • Pool available: indoor pool. hours vary based upon season
  • Four star Downtown property
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From$139
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites in Dover
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 +1-888-455-5160 ~28.78 miles east of Chestertown
  • Pool in hotel
  • 3-star Suburban property
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From$83
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 +1-888-965-8297 ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • Midscale Downtown hotel
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From$85
Very Good 4.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor : 625 South President St.
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
625 South President St., Baltimore, MD 21202 +1-888-906-6358 ~29.09 miles west of Chestertown
  • Our hotel comes with a pool
  • 3-star Downtown hotel
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From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Baltimore Marriott Waterfront
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
700 Aliceanna St., Baltimore, MD 21202 +1-888-749-6785 ~29.10 miles west of Chestertown
  • We have a pool
  • 4-star Downtown hotel
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From$150
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Wyndham Garden Dover Downtown in Dover
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
561 North Dupont Highway, Dover, DE 19901 +1-888-878-9982 ~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.
  • Three Star Downtown hotel
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From$71
Average 3.0 /5 Hotel Reviews Call BookMore Details
Roost Baltimore : 2460 Terrapin Way
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
2460 Terrapin Way, Baltimore, MD 21215 +1-888-389-4485 ~29.19 miles west of Chestertown
  • Has swimming pool: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • Four star hotel
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From$129
Average 3.0 /5 Read 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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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
6323 Ritchie Highway, Glen Burnie, MD 21061 +1-888-389-4121 ~29.21 miles west of Chestertown
  • Pool in hotel: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3-star Suburban hotel
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From$75
Average 3.0 /5 Review Score Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie : 6600 Ritchie Highway
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 +1-888-675-2083 ~29.23 miles west of Chestertown
  • Has swimming pool: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Cheap Airport property
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From$57
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Easton
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
8561 Ocean Gateway, Easton, MD 21601 +1-800-716-8490 ~29.32 miles south of Chestertown
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3-star Rural property
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From$115
Average 3.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites in North East
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 +1-800-805-5223 ~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 hotel
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From$67
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn - Towson
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 +1-888-965-1860 ~29.62 miles west of Chestertown
  • Pool details: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Cheap Suburban property
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From$56
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21202 +1-888-788-5576 ~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
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From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor - Baltimore
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
131 East Redwood St., Baltimore, MD 21202 +1-888-897-9207 ~29.67 miles west of Chestertown
  • Includes a 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.
  • 3 star Downtown property
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From$89
Very Good 4.5 /5 Review Score Call BookMore Details
Hyatt Regency Baltimore Inner Harbor in Baltimore
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 +1-888-311-4278 ~29.71 miles west of Chestertown
  • Includes a pool
  • 4-star Convention Center property
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From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 +1-888-469-4795 ~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.
  • Mid-scale Suburban property
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From$80
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Dover, DE - Dover
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 +1-888-734-9421 ~29.76 miles east of Chestertown
  • Includes a pool: 6am - 10pm
  • Two-star Downtown hotel
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From$99
Very Good 4.0 /5 Review Score Call BookMore Details
Embassy Suites Baltimore Inner Harbor in Baltimore
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
222 Saint Paul Pl, Baltimore, MD 21202 +1-888-841-5292 ~29.79 miles west of Chestertown
  • Has swimming pool: 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.
  • 4 star Downtown hotel
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From$69
Average 3.0 /5 Recent Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor : 100 Hopkins Pl
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
100 Hopkins Pl, Baltimore, MD 21201 +1-888-455-5160 ~29.93 miles west of Chestertown
  • Includes a pool: Outdoor pool (seasonal)
  • 3 star Downtown property
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From$73
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Inner Harbor
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
301 West Lombard St., Baltimore, MD 21201 +1-888-965-8297 ~30.05 miles west of Chestertown
  • Pool details: ***** 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'
  • Three Star Downtown property
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From$70
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel : 1100 Cromwell Bridge Rd.
+1-888-906-6358

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1100 Cromwell Bridge Rd., Towson, MD 21286 +1-888-906-6358 ~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.
  • 3-star Suburban hotel
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From$69
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Baltimore Inner Harbor in Baltimore
+1-888-749-6785

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401 West Pratt St., Baltimore, MD 21201 +1-888-749-6785 ~30.07 miles west of Chestertown
  • Has swimming pool: The Hilton Baltimore has a 30ft two lane track pool.
  • Expensive Downtown hotel
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From$99
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis : 210 Holiday Court
+1-888-878-9982

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210 Holiday Court, Annapolis, MD 21401 +1-888-878-9982 ~30.10 miles southwest of Chestertown
  • Has swimming pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Affordable Suburban hotel
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From$149
Average 3.0 /5 Recent Reviews Call BookMore Details
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