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 Grasonville near Kent Island - Grasonville
+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
  • We have a pool
  • Inexpensive Resort property
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From$74
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Best Western Kent Narrows Inn
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
3101 Main St., Grasonville, MD 21638 +1-888-675-2083 ~19.04 miles southwest of Chestertown
  • Pool details: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Affordable Resort hotel
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From$70
Average 3.0 /5 Hotel Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md : 20 Newton Rd.
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
20 Newton Rd., Aberdeen, MD 21001 +1-800-716-8490 ~20.61 miles north of Chestertown
  • Has swimming pool: **Pool is temporarily closed for extensive maintenance.
  • Cheap Suburban hotel
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From$60
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel - Belcamp
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1326 Policy Dr., Belcamp, MD 21017 +1-800-805-5223 ~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • 3 star Suburban property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Wingate by Wyndham Bel Air I 95 Exit 77a / Apg Area
+1-888-965-1860

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1807 Edgewood Rd., Edgewood, MD 21040 +1-888-965-1860 ~21.05 miles northwest of Chestertown
  • With a pool!
  • Three Star Suburban property
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From$54
Average 3.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen
+1-888-788-5576

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1357 Belcamp Rd., Belcamp, MD 21017 +1-888-788-5576 ~21.21 miles northwest of Chestertown
  • Has swimming pool: Our indoor heated pool is open from 7 am to 10 pm.
  • Mid-scale Rural property
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From$89
Average 3.0 /5 Hotel Reviews Call BookMore Details
Homewood Suites by Hilton Bel Air : 4170 Philadelphia Rd.
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
4170 Philadelphia Rd., Bel Air, MD 21015 +1-888-897-9207 ~21.26 miles northwest of Chestertown
  • Pool details: 9 AM - 10 PM During Covid 19 we are limiting the amount of people in pool area and scheduling pool time at front desk
  • Midscale Suburban hotel
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From$159
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD : 1435 Handlir Dr.
+1-888-311-4278

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1435 Handlir Dr., Bel Air, MD 21015 +1-888-311-4278 ~21.29 miles northwest of Chestertown
  • Pool in hotel: Outdoor Pool, open Memorial Day - Labor Day
  • Midscale Rural hotel
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From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South
+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
  • Three Star Suburban hotel
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From$95
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Aberdeen in Aberdeen
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
1050 Beards Hill Rd., Aberdeen, MD 21001 +1-888-734-9421 ~22.48 miles north of Chestertown
  • Pool in hotel: FREE INDOOR W/ HOT TUB
  • Midscale Suburban hotel
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From$110
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-841-5292 ~22.51 miles north of Chestertown
  • Has swimming pool: Enjoy a relaxing dip in our indoor-heated salt water pool. The pool is located on the first floor and has direct access to our outdoor patio area. Pool is open daily from 8am-10pm.
  • Midscale Highway property
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From$147
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites Baltimore/Aberdeen
+1-888-455-5160

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795 West Bel Air Ave., Aberdeen, MD 21001 +1-888-455-5160 ~22.63 miles north of Chestertown
  • Pool details: Indoor pool
  • 2-star Highway property
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From$89
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Fairfield Inn N Stes 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 ~22.77 miles north of Chestertown
  • We have a pool
  • 3-star hotel
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From$90
Very Good 4.0 /5 Reviews Call BookMore Details
Country Inn & Suites by Radisson, Baltimore North, MD
+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
  • Has swimming pool: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • Affordable Suburban hotel
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From$80
Average 3.0 /5 Review Score Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh : 8477 Cordon Way
+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.
  • Affordable Suburban property
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From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown - Middletown
+1-888-878-9982

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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
  • Midscale Suburban hotel
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From$70
Very Good 4.5 /5 Read Reviews Call BookMore Details
Hampton Inn Middletown
+1-888-389-4485

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117 Sandhill Dr., Middletown, DE 19709 +1-888-389-4485 ~24.53 miles northeast of Chestertown
  • Our hotel comes with a pool
  • Three Star Suburban property
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From$94
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Denton Inn - Denton
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
521 Fleetwood Rd., Denton, MD 21629 +1-888-389-4121 ~25.35 miles southeast of Chestertown
  • Has swimming pool
  • Midscale Highway hotel
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From$68
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center in Baltimore
+1-888-675-2083

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5625 O'donnell St., Baltimore, MD 21224 +1-888-675-2083 ~26.13 miles west of Chestertown
  • Has swimming pool: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Affordable Highway hotel
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From$72
Average 3.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Dover - Dover
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 +1-800-716-8490 ~27.40 miles east of Chestertown
  • Has swimming pool: Pool open daily form 8am-10pm.
  • Mid-scale Suburban hotel
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From$84
Very Good 4.5 /5 Read Reviews Call BookMore Details
Bally's Dover Casino Resort - Dover
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
1131 North Dupont Highway, Dover, DE 19901 +1-800-805-5223 ~28.36 miles east of Chestertown
  • Pool available: Open Daily 7:00 AM to 10:00 PM In-door Heated Pool
  • Expensive Resort hotel
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From$99
Very Good 4.5 /5 Recent Reviews Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-888-965-1860

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100 Westgate Cir, Annapolis, MD 21401 +1-888-965-1860 ~28.40 miles southwest of Chestertown
  • Pool details: indoor pool. hours vary based upon season
  • 4-star Downtown property
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From$139
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites : 764 Dover Leipsic Rd.
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 +1-888-788-5576 ~28.78 miles east of Chestertown
  • Includes a swimming pool
  • Affordable Suburban hotel
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From$83
Very Good 4.5 /5 Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor in Baltimore
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 +1-888-897-9207 ~28.89 miles west of Chestertown
  • Includes a pool: INDOOR POOL
  • 3 star Downtown property
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From$85
Very Good 4.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor - Baltimore
+1-888-311-4278

How should we direct your call?

New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
625b South President St., Baltimore, MD 21202 +1-888-311-4278 ~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 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore
+1-888-469-4795

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625a South President St., Baltimore, MD 21202 +1-888-469-4795 ~29.09 miles west of Chestertown
  • With a pool!
  • Midscale Downtown hotel
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From$80
Very Good 4.5 /5 Latest Reviews Call BookMore Details
Residence Inn Dover
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
600 Jefferic Blvd., Dover, DE 19901 +1-888-734-9421 ~29.10 miles east of Chestertown
  • With a pool!
  • High end Suburban hotel
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From$125
Average 3.0 /5 Read Reviews Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
561 North Dupont Highway, Dover, DE 19901 +1-888-841-5292 ~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.
  • Midscale Downtown hotel
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From$71
Average 3.0 /5 Latest Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie in Glen Burnie
+1-888-455-5160

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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
  • Has swimming pool: Outdoor pool, Opens seasonally from Memorial Day to Labor Day. Pool hours are from 11:00am-8:00pm
  • Economical Airport property
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From$57
Average 3.0 /5 Recent Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-965-8297

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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
  • Pool details: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Three Star Rural hotel
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From$115
Average 3.0 /5 Recent Reviews Call BookMore Details
Quality Inn in 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
  • Has swimming pool: 9:00am-9:00pm Outdoor Pool
  • Economy Rural property
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From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-888-749-6785

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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 hotel
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From$67
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn
+1-888-878-9982

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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 Cost Suburban property
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From$56
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Renaissance Baltimore Harborplace Hotel in Baltimore
+1-888-389-4485

How should we direct your call?

New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
202 East Pratt St., Baltimore, MD 21202 +1-888-389-4485 ~29.62 miles west of Chestertown
  • Has swimming pool
  • 4-star Downtown hotel
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From$144
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor in 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
  • Pool in hotel: Indoor pool. Pool hours from Labor Day to Memorial Day are Monday thru Friday 4:00PM to 9:00PM & Saturday to Sunday 10:00AM to 9:00PM. Pool hours from Memorial Day to Labor Day are Monday thru Thursday 4:00PM to 9:00PM & Friday thru Sunday, 10:00AM to 9:00PM.
  • 3 star Downtown property
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From$89
Very Good 4.5 /5 Read Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor in Baltimore
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 +1-888-675-2083 ~29.71 miles west of Chestertown
  • Pool in hotel
  • Four-star Convention Center hotel
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From$125
Average 3.0 /5 Read Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel : 173 Jennifer Rd.
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 +1-800-716-8490 ~29.76 miles southwest of Chestertown
  • Pool available: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Hours vary.
  • Three Star Suburban property
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From$80
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor
+1-800-805-5223

How should we direct your call?

New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
222 Saint Paul Pl, Baltimore, MD 21202 +1-800-805-5223 ~29.79 miles west of Chestertown
  • Pool details: 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.
  • Expensive Downtown hotel
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From$69
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
Hampton Inn 124, Annapolis, MD 21401 +1-888-965-1860 ~29.81 miles southwest of Chestertown
  • Pool available: Seasonal outdoor pool
  • Affordable Highway hotel
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From$80
Average 3.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-788-5576

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1100 Cromwell Bridge Rd., Towson, MD 21286 +1-888-788-5576 ~30.06 miles west of Chestertown
  • Has swimming pool: 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.
  • Mid-scale Suburban hotel
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From$69
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis : 210 Holiday Court
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
210 Holiday Court, Annapolis, MD 21401 +1-888-897-9207 ~30.10 miles southwest of Chestertown
  • Pool in hotel: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Affordable Suburban property
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From$149
Average 3.0 /5 Guest Reviews Call BookMore Details
Best Western Annapolis
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
2520 Riva Rd., Annapolis, MD 21401 +1-888-311-4278 ~30.17 miles southwest of Chestertown
  • Pool available: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 2 star Suburban hotel
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From$84
Average 3.0 /5 Recent Reviews Call BookMore Details
Wingate by Wyndham North East
+1-888-469-4795

How should we direct your call?

New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
39 Elwoods Rd., North East, MD 21901 +1-888-469-4795 ~30.29 miles north of Chestertown
  • Pool details: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • Three Star Rural property
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From$71
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Annapolis
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
124 Womack Dr., Annapolis, MD 21401 +1-888-734-9421 ~30.39 miles southwest of Chestertown
  • Includes a pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Affordable Suburban property
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From$70
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Sonesta Es Suites Annapolis
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
170 Admiral Cochrane Dr., Annapolis, MD 21401 +1-888-841-5292 ~30.57 miles southwest of Chestertown
  • Pool in hotel: Seasonal Outdoor Pool
  • Three Star Suburban property
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From$99
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Galaxy Inn in Dover
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
1700 East Lebanon Rd., Dover, DE 19901 +1-888-455-5160 ~31.11 miles east of Chestertown
  • Pool in hotel: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Midscale Suburban property
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From$70
Average 3.5 /5 Guest Reviews Call BookMore Details
Hampton / Home2 Suites Towson
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
21 West Susquehanna Ave., Towson, MD 21204 +1-888-965-8297 ~31.53 miles west of Chestertown
  • Pool available: Indoor Pool 9 AM - 10 PM
  • Affordable Downtown property
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From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Sheraton Baltimore North Hotel : 903 Dulaney Valley Rd.
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
903 Dulaney Valley Rd., Towson, MD 21204 +1-888-906-6358 ~31.60 miles west of Chestertown
  • Includes a pool: Hotel has an indoor pool with life guard on duty. Pool hours vary will need to consult your sales manager if mandatory times are required
  • Four star Suburban property
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From$103
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Elkton - Elkton
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
2 Warner Rd., Elkton, MD 21921 +1-888-749-6785 ~32.48 miles northeast of Chestertown
  • Pool available: 9am- 10pm
  • Three Star Highway hotel
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From$119
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Delta Marriott Baltimore North
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
5100 Falls Rd., Baltimore, MD 21210 +1-888-878-9982 ~32.56 miles west of Chestertown
  • Pool details: Large Outdoor Seasonal Pool staffed with lifeguard, open 10 am - dusk daily, Memorial Day to Labor Day.
  • Mid-scale Suburban hotel
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From$74
Very Good 4.0 /5 Read Reviews Call BookMore Details
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