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

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
150 Scheeler Road, Chestertown, MD 21620 +1-888-389-4121
  • Pool details: Pool umbrellas, Pool hoist on site, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from June 21 to September 01. Pool access available from 8:00 AM to 8:00 PM.
  • 3 star property
  • 20 suites in hotel
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Mariners Motel
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
5681 South Hawthorne Avenue, Rock Hall, MD MD21661 +1-888-675-2083 ~10.79 miles west of Chestertown
  • We have a pool ready for use
  • Low Cost Motel hotel
  • Check-in: 15:00:00
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Quality Inn Grasonville near Kent Island
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
101 Vfw Ave, Grasonville, MD 21638 +1-800-716-8490 ~18.56 miles southwest of Chestertown
  • Pool available: 24-hour pool access, Outdoor seasonal pool. The seasonal pool will be open from May to October. 24-hour pool access
  • Mid-scale hotel
  • Check in time: 3:00 PM
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Average 7.8 /10 Reviews Call BookMore Details
Holiday Inn Express Annapolis East-Kent Island by IHG
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1020 Kent Narrows Rd, Grasonville, MD 21638 +1-800-805-5223 ~18.92 miles southwest of Chestertown
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May to September. Pool access available from 9 AM to 9 PM.
  • Midscale hotel
  • Pets are Allowed
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Excellent 9.2 /10 Hotel Reviews Call BookMore Details
Best Western Kent Narrows Inn
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
3101 Main Street, Grasonville, MD 21638 +1-888-965-1860 ~19.09 miles southwest of Chestertown
  • Pool available: Pool hoist on site, Wheelchair-accessible pool.
  • 3 star property
  • 92 rooms in hotel
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Very Good 8.0 /10 Review Score Call BookMore Details
Hyatt Place Kent Narrows & Marina
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
3028 KENT NARROW WAY S, Grasonville, MD 21638 +1-888-788-5576 ~19.13 miles southwest of Chestertown
  • Pool details: Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers.
  • Three Star hotel
  • Pets are Welcome
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Excellent 9.4 /10 Read Reviews Call BookMore Details
Hilton Garden Inn Kent Island Marina
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
3206 Main St, Grasonville, MD 21638 +1-888-897-9207 ~19.17 miles southwest of Chestertown
  • Includes a pool: Pool hoist on site, Wheelchair-accessible pool, Pool sun loungers. Pool access available from 5 AM to 11 PM.
  • 3 star hotel
  • Pets are Welcome
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Excellent 9.0 /10 Read Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen MD
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
20 Newton Road, Aberdeen, MD 21001 +1-888-311-4278 ~20.61 miles north of Chestertown
  • Pool in hotel: Swimming pool, Wheelchair-accessible pool. Pool access available from 10:00 AM to 10 PM.
  • Three Star hotel
  • Fitness + Health Center
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Very Good 8.8 /10 Guest Reviews Call BookMore Details
Holiday Inn Belcamp - Aberdeen Area by IHG
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1326 Policy Dr, Belcamp, MD 21017 +1-888-469-4795 ~20.98 miles northwest of Chestertown
  • Pool in hotel
  • Midscale property
  • Hotel has 3 floors
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Very Good 8.4 /10 Review Score Call BookMore Details
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1807 Edgewood Rd, Edgewood, MD 21040 +1-888-734-9421 ~21.13 miles northwest of Chestertown
  • With a pool!
  • Midscale hotel
  • Free complimentary breakfast
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Average 6.8 /10 Reviews Call BookMore Details
Americas Best Value Inn Edgewood
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
1709 Edgewood Road, Edgewood, MD 21040 +1-888-841-5292 ~21.15 miles northwest of Chestertown
  • Pool details: Pool hoist on site, Wheelchair-accessible pool.
  • Cheap property
  • Hotel has 134 rooms
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Average 6.2 /10 Read Reviews Call BookMore Details
The Inn at Chesapeake Bay Beach Club
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
180 Pier One Road, Stevensville, MD 21666 +1-888-455-5160 ~21.19 miles southwest of Chestertown
  • Has swimming pool: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • Four star property
  • Hotel has 77 rooms
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Excellent 9.4 /10 Guest Reviews Call BookMore Details
Ramada Hotel & Conference Center by Wyndham Edgewood
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
1700 Van Bibber Rd, Edgewood, MD 21040 +1-888-965-8297 ~21.20 miles northwest of Chestertown
  • Includes a pool: Pool umbrellas, Wheelchair-accessible pool, Outdoor seasonal pool, Pool sun loungers, Fence around pool. The seasonal pool will be open from May 31 to September 30. Pool access available from 10:00 AM to 8:30 PM.
  • 2 star hotel
  • 2 suites in property
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Average 6.6 /10 Latest Reviews Call BookMore Details
TownePlace Suites by Marriott Edgewood Aberdeen
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
1357 Belcamp Rd, Aberdeen, MD 21017 +1-888-906-6358 ~21.20 miles northwest of Chestertown
  • Has swimming pool: Wheelchair-accessible pool. Pool access available from 7:00 AM to 9:00 PM.
  • Affordable hotel
  • Check in: 3:00 PM
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Excellent 9.0 /10 Reviews Call BookMore Details
Kent Island Resort
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
500 Kent Manor Dr, Stevensville, MD 21666 +1-888-749-6785 ~21.23 miles southwest of Chestertown
  • Has swimming pool: Pool umbrellas, Swimming pool, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from April to November. Pool access available from 8:00 AM to 8:00 PM.
  • Three Star hotel
  • Hotel has 2 suites
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Excellent 9.2 /10 Latest Reviews Call BookMore Details
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
2118 Emmorton Park Dr, Edgewood, MD 21040 +1-888-878-9982 ~21.25 miles northwest of Chestertown
  • Pool available: Swimming pool.
  • Three Star hotel
  • Free breakfast
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Excellent 9.0 /10 Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
4170 Philadelphia Road, Bel Air, MD 21015 +1-888-389-4485 ~21.25 miles northwest of Chestertown
  • Pool available: Wheelchair-accessible pool. Pool access available from 10:00 AM to 7:00 PM.
  • Affordable property
  • Has environment-friendly policy Read more
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Very Good 8.8 /10 Read Reviews Call BookMore Details
Hilton Garden Inn Bel Air
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
4160 Philadelphia Road, Bel Air, MD 21015 +1-888-389-4121 ~21.27 miles northwest of Chestertown
  • Has swimming pool: Wheelchair-accessible pool, Pool sun loungers.
  • Affordable hotel
  • 102 rooms in property
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Excellent 9.2 /10 Read Reviews Call BookMore Details
SpringHill Suites by Marriott Edgewood / Aberdeen
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
1420 Handlir Dr, Bel Air, MD 21015 +1-888-675-2083 ~21.29 miles northwest of Chestertown
  • Pool details: Wheelchair-accessible pool. Pool access available from 6 AM to 10 PM.
  • Mid-scale hotel
  • 119 rooms in hotel
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Very Good 8.8 /10 Review Score Call BookMore Details
Country Inn & Suites by Radisson Bel Air / Aberdeen, MD
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
1435 Handlir Dr, Bel Air, MD 21015 +1-800-716-8490 ~21.30 miles northwest of Chestertown
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool. The seasonal pool will be open from May to September.
  • 3 star property
  • Complimentary breakfast is offered
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Very Good 8.8 /10 Reviews Call BookMore Details
Candlewood Suites Aberdeen-Bel Air by IHG
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
4216 Philadelphia Rd, Bel Air, MD 21015 +1-800-805-5223 ~21.35 miles northwest of Chestertown
  • Includes a pool: Pool umbrellas, Outdoor seasonal pool, Pool sun loungers. The seasonal pool will be open from May 29 to September 15.
  • Midscale hotel
  • Check in: 4:00 PM - anytime
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Very Good 8.2 /10 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Edgewood / Aberdeen-South
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
2110 Emmorton Park Rd, Edgewood, MD 21040 +1-888-965-1860 ~21.36 miles northwest of Chestertown
  • Pool details: Wheelchair-accessible pool.
  • Affordable property
  • 134 rooms in property
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Excellent 9.4 /10 Hotel Reviews Call BookMore Details
Hilton Garden Inn Aberdeen
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1050 Beards Hill Rd, Aberdeen, MD 21001 +1-888-788-5576 ~22.44 miles north of Chestertown
  • Pool in hotel: Swimming pool. Pool access available from 5 AM to 10 PM.
  • Mid-scale hotel
  • Hotel has 96 rooms
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Very Good 8.6 /10 Latest Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
783 West Bel Air Ave, Aberdeen, MD 21001 +1-888-897-9207 ~22.46 miles north of Chestertown
  • Includes a pool: Outdoor seasonal pool, Access to nearby outdoor pool. The seasonal pool will be open from May to September. Pool access available from 10 AM to 9 PM.
  • 2 star Motel property
  • 2 suites in property
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Average 7.2 /10 Guest Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1007 Beards Hill Rd, Aberdeen, MD 21001 +1-888-311-4278 ~22.54 miles north of Chestertown
  • Has swimming pool
  • Three Star hotel
  • Gym / Fitness Center Available
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Very Good 8.6 /10 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore / Aberdeen
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
795 West Bel Air Ave, Aberdeen, MD 21001 +1-888-469-4795 ~22.62 miles north of Chestertown
  • Pool available: Wheelchair-accessible pool.
  • 3-star property
  • Pets are Welcome
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Excellent 9.0 /10 Latest Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen-APG
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
793 West Bel Air Ave, Aberdeen, MD 21001 +1-888-734-9421 ~22.62 miles north of Chestertown
  • Pool available: Wheelchair-accessible pool, Outdoor seasonal pool. The seasonal pool will be open from May to August.
  • Mid-scale hotel
  • 85 rooms in property
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Excellent 9.0 /10 Recent Reviews Call BookMore Details
Travelodge by Wyndham Aberdeen
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
820 West Bel Air Ave, Aberdeen, MD 21001 +1-888-841-5292 ~22.68 miles north of Chestertown
  • Has swimming pool: Swimming pool, Billiards or pool table, Outdoor seasonal pool, Children's pool. The seasonal pool will be open from May to September. Pool access available from 10 AM to 9 PM.
  • Two-star hotel
  • 2 floors in property
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Average 6.4 /10 Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen near APG
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
980 Hospitality Way, Aberdeen, MD 21001 +1-888-455-5160 ~22.70 miles north of Chestertown
  • Pool details: Outdoor seasonal pool. The seasonal pool will be open from May to September. Pool access available from 9:00 AM to 7:00 PM.
  • Three Star property
  • 4 floors in hotel
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Very Good 8.0 /10 Latest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott Aberdeen
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
907 BARNETT LANE, Aberdeen, MD 21001 +1-888-965-8297 ~22.76 miles north of Chestertown
  • Pool in hotel: Wheelchair-accessible pool.
  • Affordable hotel
  • 4 floors in hotel
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Very Good 8.8 /10 Guest Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / White Marsh
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
10465 Philadelphia Road, White Marsh, MD 21162 +1-888-906-6358 ~23.06 miles northwest of Chestertown
  • Has swimming pool: Wheelchair-accessible pool. Pool access available from 5:00 PM to 9 PM.
  • Affordable hotel
  • 4 floors in hotel
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Very Good 8.2 /10 Read Reviews Call BookMore Details
Holiday Inn Express White Marsh by IHG
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
10542 Philadelphia Road, Perry Hall, MD 21162 +1-888-749-6785 ~23.16 miles northwest of Chestertown
  • Pool available: Pool access available from 7:00 AM to 10:00 PM.
  • Affordable property
  • Check in: 3:00 PM - anytime
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Excellent 9.4 /10 Hotel Reviews Call BookMore Details
Courtyard Aberdeen at Ripken Stadium
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
830 Long Drive, Aberdeen, MD 21001 +1-888-878-9982 ~23.19 miles north of Chestertown
  • Pool available: Wheelchair-accessible pool.
  • 3 star hotel
  • 7 floors in hotel
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Very Good 8.6 /10 Guest Reviews Call BookMore Details
Residence Inn Aberdeen at Ripken Stadium
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
830 Long Drive, Aberdeen, MD 21001 +1-888-389-4485 ~23.19 miles north of Chestertown
  • Pool available: Wheelchair-accessible pool.
  • Affordable hotel
  • Hotel has an eco-friendly policy Read more
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Excellent 9.0 /10 Reviews Call BookMore Details
First Floor Standard Suite Bay View
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-389-4121 ~23.59 miles north of Chestertown
  • Pool in hotel: Billiards or pool table.
  • 2 star hotel
  • Fitness + Health Center
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Top Floor Standard Deluxe
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-675-2083 ~23.59 miles north of Chestertown
  • Pool details: Billiards or pool table.
  • Affordable hotel
  • Check-in: 4:00 PM
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Excellent 10.0 /10 Recent Reviews Call BookMore Details
Second Floor Deluxe Suite Bay View
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-800-716-8490 ~23.59 miles north of Chestertown
  • Includes a pool: Billiards or pool table.
  • Inexpensive hotel
  • Gym is available on property
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First Floor East Family Deluxe
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-800-805-5223 ~23.59 miles north of Chestertown
  • Pool in hotel: Billiards or pool table.
  • 3-star property
  • Gym / Fitness Center Available
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Top Floor Standard Suite Bay View
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-965-1860 ~23.59 miles north of Chestertown
  • Has swimming pool: Billiards or pool table.
  • Three Star hotel
  • Check in time: 4:00 PM
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First Floor Standard Deluxe
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-788-5576 ~23.59 miles north of Chestertown
  • Pool details: Billiards or pool table.
  • Two star hotel
  • Fitness center on property
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Second Conference Standard Suite Bay View
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-897-9207 ~23.59 miles north of Chestertown
  • Has swimming pool: Billiards or pool table.
  • Low-priced property
  • Gym is available on property
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Top Floor East Family Deluxe
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-311-4278 ~23.59 miles north of Chestertown
  • Pool details: Billiards or pool table.
  • Inexpensive hotel
  • Check-in time: 4:00 PM
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Second Floor Master Suite Bay View
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-469-4795 ~23.59 miles north of Chestertown
  • Pool in hotel: Billiards or pool table.
  • 3 star hotel
  • Fitness center on property
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Second Floor Standard Deluxe
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-734-9421 ~23.59 miles north of Chestertown
  • Has swimming pool: Billiards or pool table.
  • Economical hotel
  • Gym is available on property
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First Floor Standard Deluxe King
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-841-5292 ~23.59 miles north of Chestertown
  • Pool in hotel: Billiards or pool table.
  • Mid-scale hotel
  • Gym / Fitness Center Available
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Top Floor Family Deluxe Bay View
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-455-5160 ~23.59 miles north of Chestertown
  • Pool details: Billiards or pool table.
  • Mid-scale property
  • Fitness center on property
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Second Conference Family Deluxe
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-965-8297 ~23.59 miles north of Chestertown
  • Includes a pool: Billiards or pool table.
  • 3 star hotel
  • Gym / Fitness Center Available
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Second East Family Deluxe
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-906-6358 ~23.59 miles north of Chestertown
  • Pool details: Billiards or pool table.
  • Three Star hotel
  • Check in time: 4:00 PM
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Second Conference Standard Deluxe Bay View
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-749-6785 ~23.59 miles north of Chestertown
  • Pool available: Billiards or pool table.
  • Two-star property
  • Check in time: 4:00 PM
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Top Floor Handicap Accessible Bay View
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
60 Sandy Cove Road, North East, MD 21901 +1-888-878-9982 ~23.59 miles north of Chestertown
  • Has swimming pool: Billiards or pool table.
  • Midscale property
  • Check-in time: 4:00 PM
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