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 - Chestertown
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
150 Scheeler Rd., Chestertown, MD 21620 +1-888-389-4121
  • Pool available: Outdoor seasonal pool. Open 8am-10pm
  • Three Star Suburban property
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From$90
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
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 +1-888-675-2083 ~18.94 miles southwest of Chestertown
  • Has swimming pool: Outdoor pool open from Memorial day to labor day 9am-9pm
  • Mid-scale Rural hotel
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From$180
Very Good 4.0 /5 Reviews 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
  • Pool in hotel: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Affordable Resort hotel
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Kent Island - Grasonville
+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 in hotel: Indoor pool open daily 5 AM-11PM
  • Three Star Riverfront property
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From$121
Very Good 4.0 /5 Review Score Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md - Aberdeen
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
20 Newton Rd., Aberdeen, MD 21001 +1-888-965-1860 ~20.61 miles north of Chestertown
  • Pool details: **Pool is temporarily closed for extensive maintenance.
  • Cheap Suburban property
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From$60
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1326 Policy Dr., Belcamp, MI 21017 +1-888-788-5576 ~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Mid-scale Suburban property
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen - Belcamp
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
1357 Belcamp Rd., Belcamp, MD 21017 +1-888-897-9207 ~21.21 miles northwest of Chestertown
  • Has swimming pool: Our indoor pool opens from 7 am to 10 pm.
  • 4-star Rural property
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From$89
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air, an IHG Hotel
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
2118 Emmorton Park Rd., Edgewood, MD 21040 +1-888-311-4278 ~21.22 miles northwest of Chestertown
  • Has swimming pool
  • 3 star Suburban property
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From$119
Very Good 4.0 /5 Guest Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen : 1420 Handlir Dr.
+1-888-469-4795

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1420 Handlir Dr., Bel Air, MD 21015 +1-888-469-4795 ~21.27 miles northwest of Chestertown
  • We have a pool ready for use
  • 3 star Highway property
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From$106
Very Good 4.0 /5 Reviews Call BookMore Details
Country Inn & Suites by Radisson Bel Air / Aberdeen Md in Bel Air
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1435 Handlir Dr., Bel Air, MD 21015 +1-888-734-9421 ~21.29 miles northwest of Chestertown
  • Includes a pool: Outdoor Pool, open Memorial Day - Labor Day
  • Mid-scale Rural hotel
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From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
2110 Emmorton Park Rd., Edgewood, MD 21040 +1-888-841-5292 ~21.33 miles northwest of Chestertown
  • Includes a pool: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban property
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From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Kent Island Resort
+1-888-455-5160

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500 Kent Manor Dr., Stevensville, MD 21666 +1-888-455-5160 ~21.50 miles southwest of Chestertown
  • Includes a pool: Outdoor (seasonal pool)
  • High end Riverfront hotel
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From$125
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
1050 Beards Hill Rd., Aberdeen, MD 21001 +1-888-965-8297 ~22.48 miles north of Chestertown
  • Has swimming pool
  • 3 star Suburban property
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From$110
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Aberdeen
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-906-6358 ~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 property
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From$147
Very Good 4.0 /5 Read 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
  • 3 star Highway property
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From$84
Average 3.0 /5 Guest 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
  • Has swimming pool: Indoor Pool
  • Mid-scale Suburban hotel
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From$83
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh - Baltimore
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
5015 Campbell Blvd., Baltimore, MD 21236 +1-888-389-4485 ~23.76 miles west of Chestertown
  • Pool available: Indoor Pool
  • Mid-scale Suburban hotel
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From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh in Nottingham
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
8225 Town Center Dr., Nottingham, MD 21236 +1-888-389-4121 ~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 hotel
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From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh
+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
  • Includes a pool: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • Mid-scale Suburban property
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From$109
Average 3.0 /5 Review Score Call BookMore Details
Country Inn & Suites by Radisson, Baltimore North, MD - Rosedale
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
8825 Yellow Brick Rd., Rosedale, MD 21237 +1-800-716-8490 ~23.90 miles west of Chestertown
  • Pool available: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Midscale Suburban hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh
+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
  • 3-star Suburban hotel
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From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown : 315 Auto Park Dr.
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
315 Auto Park Dr., Middletown, DE 19709 +1-888-965-1860 ~24.19 miles northeast of Chestertown
  • Pool in hotel: Indoor Pool, open year round
  • 3-star Suburban property
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From$70
Very Good 4.5 /5 Guest Reviews Call BookMore Details
Hampton Inn Middletown : 117 Sandhill Dr.
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
117 Sandhill Dr., Middletown, DE 19709 +1-888-788-5576 ~24.53 miles northeast of Chestertown
  • Pool in hotel
  • Three Star Suburban property
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From$94
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Denton Inn in Denton
+1-888-897-9207

How should we direct your call?

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
  • Includes a pool
  • Affordable Highway hotel
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From$67
Very Good 4.0 /5 Hotel 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 details: Indoor/Heated Pool Lifeguard on duty M-F 5pm - 10pm Sat/Sun 9am -10pm Summer Fri 12p-10p
  • Affordable Suburban property
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From$89
Average 3.0 /5 Read Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
5625 O'donnell St., Baltimore, MD 21224 +1-888-469-4795 ~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Midscale Highway property
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From$72
Average 3.0 /5 Review Score 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
  • Has swimming pool: Pool open daily form 8am-10pm.
  • Midscale Suburban hotel
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From$84
Very Good 4.5 /5 Latest Reviews Call BookMore Details
The Westin Annapolis in Annapolis
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 Website +1-888-841-5292 ~28.40 miles southwest of Chestertown
  • Has swimming pool: indoor pool. hours vary based upon season
  • High end Downtown hotel
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From$139
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites - Dover
+1-888-455-5160

How should we direct your call?

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
  • Affordable Suburban hotel
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From$83
Very Good 4.5 /5 Review Score Call BookMore Details
Hyatt Place Baltimore Inner Harbor : 511 South Central Ave.
+1-888-965-8297

How should we direct your call?

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
  • Includes a pool: INDOOR POOL
  • Mid-scale Downtown hotel
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From$85
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor in Baltimore
+1-888-906-6358

How should we direct your call?

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
  • We have a pool ready for use
  • 3 star Downtown hotel
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From$110
Very Good 4.0 /5 Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore Inner Harbor in Baltimore
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
625a South President St., Baltimore, MD 21202 +1-888-749-6785 ~29.09 miles west of Chestertown
  • Includes a swimming pool
  • 3 star Downtown property
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From$80
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Baltimore Marriott Waterfront : 700 Aliceanna St.
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
700 Aliceanna St., Baltimore, MD 21202 +1-888-878-9982 ~29.10 miles west of Chestertown
  • With a pool!
  • 4 star Downtown property
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From$150
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
561 North Dupont Highway, Dover, DE 19901 +1-888-389-4485 ~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.
  • Mid-scale Downtown hotel
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From$71
Average 3.0 /5 Recent Reviews Call BookMore Details
Roost Baltimore
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
2460 Terrapin Way, Baltimore, MD 21215 +1-888-389-4121 ~29.19 miles west of Chestertown
  • Has swimming pool: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • High-end hotel
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From$129
Average 3.0 /5 Review Score Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
6323 Ritchie Highway, Glen Burnie, MD 21061 +1-888-675-2083 ~29.21 miles west of Chestertown
  • Has swimming pool: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3 star Suburban property
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From$75
Average 3.0 /5 Review Score Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie in Glen Burnie
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 +1-800-716-8490 ~29.23 miles west of Chestertown
  • Pool available: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Cheap Airport property
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From$57
Average 3.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Easton in Easton
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
8561 Ocean Gateway, Easton, MD 21601 +1-800-805-5223 ~29.32 miles south of Chestertown
  • Pool in hotel: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Three Star Rural property
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From$115
Average 3.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites in North East
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 +1-888-965-1860 ~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.
  • Midscale Rural hotel
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From$67
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 +1-888-788-5576 ~29.62 miles west of Chestertown
  • Pool in hotel: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Economy Suburban hotel
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From$56
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore in Baltimore
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21202 +1-888-897-9207 ~29.64 miles west of Chestertown
  • Pool details: 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
  • Expensive Downtown hotel
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From$79
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
131 East Redwood St., Baltimore, MD 21202 +1-888-311-4278 ~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.
  • Midscale Downtown hotel
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From$89
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor : 300 Light St.
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 +1-888-469-4795 ~29.71 miles west of Chestertown
  • Our hotel comes with a pool
  • 4-star Convention Center hotel
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From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 +1-888-734-9421 ~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.
  • Affordable Suburban property
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From$80
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Home2 Suites by Hilton Dover, DE : 222 South Dupont Highway
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 +1-888-841-5292 ~29.76 miles east of Chestertown
  • Pool in hotel: 6am - 10pm
  • Low Cost Downtown property
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From$99
Very Good 4.0 /5 Read Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor - Baltimore
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
222 Saint Paul Pl, Baltimore, MD 21202 +1-888-455-5160 ~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.
  • High-end Downtown hotel
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From$69
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
Hampton Inn 124, Annapolis, MD 21401 +1-888-965-8297 ~29.81 miles southwest of Chestertown
  • Includes a pool: Seasonal outdoor pool
  • Midscale Highway property
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Radisson Hotel Baltimore Downtown Inner Harbor in Baltimore
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
101 West Fayette St., Baltimore, MD 21201 +1-888-906-6358 ~29.90 miles west of Chestertown
  • Includes a pool: Come experience our seasonal Rooftop Outdoor Pool opens Memorial Day to Labor Day.
  • 3-star Downtown hotel
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From$87
Poor 2.0 /5 Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
100 Hopkins Pl, Baltimore, MD 21201 +1-888-749-6785 ~29.93 miles west of Chestertown
  • Includes a pool: Outdoor pool (seasonal)
  • Three Star Downtown hotel
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From$73
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel in Towson
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
1100 Cromwell Bridge Rd., Towson, MD 21286 +1-888-878-9982 ~30.06 miles west of Chestertown
  • Pool available: 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 hotel
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From$69
Very Good 4.0 /5 Recent Reviews Call BookMore Details
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