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

Quality Inn
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
101 Vfw Ave., Grasonville, MD 21638 +1-888-389-4121 ~18.54 miles southwest of Chestertown
  • Has a pool!
  • 2 star Resort hotel
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From$74
Very Good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Annapolis East-Kent Island by IHG
+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
  • Includes a 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 in Grasonville
+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
  • Has swimming pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Midscale Resort property
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Hilton Garden Inn Kent Island Marina : 3206 Main St.
+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
  • Includes a pool: Indoor pool open daily 5 AM-11PM
  • Midscale Riverfront property
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From$121
Very Good 4.0 /5 Hotel 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, MD 21017 +1-888-965-1860 ~20.96 miles northwest of Chestertown
  • Pool details: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Midscale Suburban hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1807 Edgewood Rd., Edgewood, MD 21040 +1-888-788-5576 ~21.05 miles northwest of Chestertown
  • Pool in hotel
  • 3-star Suburban property
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From$54
Average 3.0 /5 Latest Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen - Belcamp
+1-888-897-9207

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1357 Belcamp Rd., Belcamp, MD 21017 +1-888-897-9207 ~21.21 miles northwest of Chestertown
  • Includes a pool: Our indoor heated pool is open from 7 am to 10 pm.
  • Affordable Rural hotel
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From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South in Edgewood
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
2110 Emmorton Park Rd., Edgewood, MD 21040 +1-888-311-4278 ~21.33 miles northwest of Chestertown
  • Pool in hotel: Indoor Pool available 6AM to 10PM
  • Affordable Suburban hotel
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From$95
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Aberdeen by IHG in Aberdeen
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-469-4795 ~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.
  • Three Star Highway hotel
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From$147
Very Good 4.0 /5 Recent Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Aberdeen Apg
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
793 West Bel Air Ave., Aberdeen, MD 21001 +1-888-734-9421 ~22.66 miles north of Chestertown
  • Pool in hotel
  • 3 star Rural hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
980 Hospitality Way, Aberdeen, MD 21001 +1-888-841-5292 ~22.75 miles north of Chestertown
  • Pool in hotel: Seasonal Large Outdoor Pool with picnic tables and grills
  • 3-star Highway property
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From$84
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh
+1-888-455-5160

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5015 Campbell Blvd., Baltimore, MD 21236 +1-888-455-5160 ~23.76 miles west of Chestertown
  • Includes a pool: Indoor Pool
  • 3-star Suburban hotel
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From$89
Average 3.0 /5 Latest Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh in Nottingham
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
8225 Town Center Dr., Nottingham, MD 21236 +1-888-965-8297 ~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.
  • 3 star Suburban property
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From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Country Inn & Suites by Radisson Baltimore North Md : 8825 Yellow Brick Rd.
+1-888-906-6358

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8825 Yellow Brick Rd., Rosedale, MD 21237 +1-888-906-6358 ~23.90 miles west of Chestertown
  • Pool details: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • 3-star Suburban property
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh in Baltimore
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
8477 Cordon Way, Baltimore, MD 21236 +1-888-749-6785 ~23.93 miles west of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • 3-star Suburban hotel
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From$89
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown - Middletown
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
315 Auto Park Dr., Middletown, DE 19709 +1-888-878-9982 ~24.19 miles northeast of Chestertown
  • Pool in hotel: Indoor Pool, open year round
  • Mid-scale Suburban hotel
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From$70
Very Good 4.5 /5 Review Score Call BookMore Details
Best Western Denton Inn - Denton
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
521 Fleetwood Rd., Denton, MD 21629 +1-888-389-4485 ~25.35 miles southeast of Chestertown
  • We have a pool ready for use
  • 3-star Highway property
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From$68
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center : 5625 O'donnell St.
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
5625 O'donnell St., Baltimore, MD 21224 +1-888-389-4121 ~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • 3 star Highway property
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From$72
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Dover
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 +1-888-675-2083 ~27.40 miles east of Chestertown
  • Pool available: Pool open daily form 8am-10pm.
  • Three Star Suburban property
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From$84
Very Good 4.5 /5 Guest Reviews Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 +1-800-716-8490 ~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 Recent Reviews Call BookMore Details
Comfort Inn & Suites - Dover
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 +1-800-805-5223 ~28.78 miles east of Chestertown
  • We have a pool ready for use
  • 3-star Suburban property
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From$83
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor in Baltimore
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 +1-888-965-1860 ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • 3-star Downtown hotel
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From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
625b South President St., Baltimore, MD 21202 +1-888-788-5576 ~29.09 miles west of Chestertown
  • We have a pool ready for use
  • 3-star Downtown property
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From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore - Baltimore
+1-888-897-9207

How should we direct your call?

New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
625a South President St., Baltimore, MD 21202 +1-888-897-9207 ~29.09 miles west of Chestertown
  • We have a pool ready for use
  • 3-star Downtown property
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From$80
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Residence Inn Dover
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
600 Jefferic Blvd., Dover, DE 19901 +1-888-311-4278 ~29.10 miles east of Chestertown
  • We have a pool ready for use
  • High-end Suburban property
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From$125
Average 3.0 /5 Latest Reviews Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-469-4795

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561 North Dupont Highway, Dover, DE 19901 +1-888-469-4795 ~29.11 miles east of Chestertown
  • Pool available: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • Affordable Downtown property
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From$71
Average 3.0 /5 Hotel Reviews Call BookMore Details
Roost Baltimore
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
2460 Terrapin Way, Baltimore, MD 21215 +1-888-734-9421 ~29.19 miles west of Chestertown
  • Pool available: 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 Hotel Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie - Glen Burnie
+1-888-841-5292

How should we direct your call?

New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
6323 Ritchie Highway, Glen Burnie, MD 21061 +1-888-841-5292 ~29.21 miles west of Chestertown
  • Has swimming pool: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • Mid-scale Suburban property
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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
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 +1-888-455-5160 ~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
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From$57
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Easton : 8561 Ocean Gateway
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
8561 Ocean Gateway, Easton, MD 21601 +1-888-965-8297 ~29.32 miles south of Chestertown
  • Includes a pool: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Midscale Rural hotel
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From$115
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn - Easton
+1-888-906-6358

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New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
8523 Ocean Gateway, Easton, MD 21601 +1-888-906-6358 ~29.37 miles south of Chestertown
  • Includes a pool: 9:00am-9:00pm Outdoor Pool
  • Cheap Rural hotel
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From$79
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 +1-888-749-6785 ~29.39 miles north of Chestertown
  • Pool available: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • Midscale Rural property
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From$67
Average 3.0 /5 Latest Reviews Call BookMore Details
Comfort Inn in Towson
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 +1-888-878-9982 ~29.62 miles west of Chestertown
  • Has swimming pool: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Low priced Suburban hotel
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From$56
Very Good 4.0 /5 Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore - Baltimore
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21202 +1-888-389-4485 ~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
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From$79
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor - Baltimore
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
131 East Redwood St., Baltimore, MD 21202 +1-888-389-4121 ~29.67 miles west of Chestertown
  • Has swimming 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 hotel
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From$89
Very Good 4.5 /5 Guest Reviews Call BookMore Details
The Royal Sonesta Harbor Court
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21230 +1-888-675-2083 ~29.68 miles west of Chestertown
  • Has swimming pool: Our rooftop indoor pool is open 5am-10pm daily
  • Four star Downtown property
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From$125
Average 3.0 /5 Read Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 +1-800-716-8490 ~29.71 miles west of Chestertown
  • Our hotel comes with a pool
  • High end Convention Center property
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From$125
Average 3.0 /5 Review Score Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel in Annapolis
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 +1-800-805-5223 ~29.76 miles southwest of Chestertown
  • Includes a pool: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Hours vary.
  • 3 star Suburban property
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From$80
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Dover De - Dover
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 +1-888-965-1860 ~29.76 miles east of Chestertown
  • Pool available: 6am - 10pm
  • Cheap Downtown property
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From$99
Very Good 4.0 /5 Review Score Call BookMore Details
Hampton Inn & Suites in Annapolis
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
Hampton Inn 124, Annapolis, MD 21401 +1-888-788-5576 ~29.81 miles southwest of Chestertown
  • Pool in hotel: Seasonal outdoor pool
  • Three Star Highway hotel
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From$80
Average 3.0 /5 Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor : 100 Hopkins Pl
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
100 Hopkins Pl, Baltimore, MD 21201 +1-888-897-9207 ~29.93 miles west of Chestertown
  • Pool available: Outdoor pool (seasonal)
  • Mid-scale Downtown hotel
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From$73
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1100 Cromwell Bridge Rd., Towson, MD 21286 +1-888-311-4278 ~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.
  • Affordable Suburban property
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From$69
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis : 210 Holiday Court
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
210 Holiday Court, Annapolis, MD 21401 +1-888-469-4795 ~30.10 miles southwest of Chestertown
  • Includes a pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Three Star Suburban property
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From$149
Average 3.0 /5 Reviews Call BookMore Details
Best Western Annapolis - Annapolis
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
2520 Riva Rd., Annapolis, MD 21401 +1-888-734-9421 ~30.17 miles southwest of Chestertown
  • Pool available: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Inexpensive Suburban property
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From$84
Average 3.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Annapolis in Annapolis
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
124 Womack Dr., Annapolis, MD 21401 +1-888-841-5292 ~30.39 miles southwest of Chestertown
  • Pool in hotel: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Affordable Suburban hotel
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From$70
Very Good 4.0 /5 Read Reviews Call BookMore Details
Sonesta Es Suites Annapolis - Annapolis
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
170 Admiral Cochrane Dr., Annapolis, MD 21401 +1-888-455-5160 ~30.57 miles southwest of Chestertown
  • Includes a pool: Seasonal Outdoor Pool
  • High end Suburban hotel
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From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Galaxy Inn
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
1700 East Lebanon Rd., Dover, DE 19901 +1-888-965-8297 ~31.11 miles east of Chestertown
  • Pool details: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • 3 star Suburban hotel
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From$70
Average 3.5 /5 Guest Reviews Call BookMore Details
Hampton / Home2 Suites Towson in Towson
+1-888-906-6358

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21 West Susquehanna Ave., Towson, MD 21204 +1-888-906-6358 ~31.53 miles west of Chestertown
  • Pool available: Indoor Pool 9 AM - 10 PM
  • 3-star Downtown property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Sheraton Baltimore North in Towson
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
903 Dulaney Valley Rd., Towson, MD 21204 +1-888-749-6785 ~31.54 miles west of Chestertown
  • Pool available: Hotel has an indoor pool. Pool is open from 7am -10pm.
  • Affordable Suburban hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Days Inn by Wyndham Easton : 7018 Ocean Gateway
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
7018 Ocean Gateway, Easton, MD 21601 +1-888-878-9982 ~32.19 miles south of Chestertown
  • Pool in hotel: out door swimming pool
  • 3-star property
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From$80
Average 3.0 /5 Review Score Call BookMore Details
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