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 in 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
  • Includes a swimming pool
  • Economy Resort hotel
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From$74
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Annapolis East-Kent Island by IHG 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
  • 3-star Rural property
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From$180
Very good 4.0 /5 Latest 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
  • Has swimming pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • 3 star Resort property
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From$80
Average 3.0 /5 Latest 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
  • Pool details: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Midscale Suburban hotel
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From$80
Average 3.0 /5 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
  • Includes a swimming pool
  • 3 star Suburban property
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From$54
Average 3.0 /5 Latest 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
  • Pool available: Our indoor heated pool is open from 7 am to 10 pm.
  • Affordable Rural property
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From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South in Edgewood
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
2110 Emmorton Park Rd., Edgewood, MD 21040 +1-888-897-9207 ~21.33 miles northwest of Chestertown
  • Has swimming pool: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban hotel
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From$95
Very good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG - Aberdeen
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
1007 Beards Hill Rd., Aberdeen, MD 21001 +1-888-311-4278 ~22.51 miles north of Chestertown
  • Includes a 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.
  • Affordable Highway hotel
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From$147
Very good 4.0 /5 Guest Reviews Call BookMore Details
Days Inn by Wyndham Aberdeen : 783 West Bel Air Ave.
+1-888-469-4795

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783 West Bel Air Ave., Aberdeen, MD 21001 +1-888-469-4795 ~22.53 miles north of Chestertown
  • Includes a pool: We have Outdoor Pool. Opens from Memorial day to labor day
  • Inexpensive Highway hotel
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From$60
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg
+1-888-734-9421

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New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
980 Hospitality Way, Aberdeen, MD 21001 +1-888-734-9421 ~22.75 miles north of Chestertown
  • Pool in hotel: Seasonal Large Outdoor Pool with picnic tables and grills
  • Affordable Highway hotel
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From$84
Average 3.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Baltimore / White Marsh : 5015 Campbell Blvd.
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
5015 Campbell Blvd., Baltimore, MD 21236 +1-888-841-5292 ~23.76 miles west of Chestertown
  • Has swimming pool: Indoor Pool
  • Affordable Suburban hotel
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From$89
Average 3.0 /5 Review Score Call BookMore Details
Hampton Inn Baltimore / White Marsh
+1-888-455-5160

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New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
8225 Town Center Dr., Nottingham, MD 21236 +1-888-455-5160 ~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 hotel
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From$89
Very good 4.0 /5 Review Score Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh
+1-888-965-8297

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New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
4980 Mercantile Rd., Baltimore, MD 21236 +1-888-965-8297 ~23.86 miles west of Chestertown
  • Has swimming pool: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • 3-star Suburban property
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From$109
Average 3.0 /5 Guest Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh
+1-888-906-6358

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8477 Cordon Way, Baltimore, MD 21236 +1-888-906-6358 ~23.93 miles west of Chestertown
  • Pool details: Seasonal Outdoor Pool opens Memorial Day and closed Labor Day
  • Affordable Suburban property
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From$89
Very good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown in Middletown
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
315 Auto Park Dr., Middletown, DE 19709 +1-888-749-6785 ~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 Reviews Call BookMore Details
Best Western Denton Inn
+1-888-878-9982

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521 Fleetwood Rd., Denton, MD 21629 +1-888-878-9982 ~25.35 miles southeast of Chestertown
  • With a pool!
  • Midscale Highway property
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From$68
Very good 4.0 /5 Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center - Baltimore
+1-888-389-4485

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New Reservations: +1-888-389-4485 Group Sales: +1-888-494-8863
5625 O'donnell St., Baltimore, MD 21224 +1-888-389-4485 ~26.13 miles west of Chestertown
  • Has swimming pool: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Three Star Highway hotel
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From$72
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Dover
+1-888-389-4121

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New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
1706 North Dupont Highway, Dover, DE 19901 +1-888-389-4121 ~27.40 miles east of Chestertown
  • Includes a pool: Pool open daily form 8am-10pm.
  • Three Star Suburban hotel
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From$84
Very good 4.5 /5 Hotel Reviews Call BookMore Details
The Westin Annapolis
+1-888-675-2083

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New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
100 Westgate Cir, Annapolis, MD 21401 +1-888-675-2083 ~28.40 miles southwest of Chestertown
  • Pool in hotel: indoor pool. hours vary based upon season
  • Expensive Downtown property
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From$139
Very good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites
+1-800-716-8490

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New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
764 Dover Leipsic Rd., Dover, DE 19901 +1-800-716-8490 ~28.78 miles east of Chestertown
  • Includes a pool
  • Mid-scale Suburban hotel
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From$83
Very good 4.5 /5 Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
511 South Central Ave., Baltimore, MD 21202 +1-800-805-5223 ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • Affordable Downtown hotel
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From$85
Very good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor - Baltimore
+1-888-965-1860

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New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
625b South President St., Baltimore, MD 21202 +1-888-965-1860 ~29.09 miles west of Chestertown
  • Includes a pool
  • 3-star Downtown hotel
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From$110
Very good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore in Baltimore
+1-888-788-5576

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New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
625a South President St., Baltimore, MD 21202 +1-888-788-5576 ~29.09 miles west of Chestertown
  • Has swimming pool
  • 3 star Downtown property
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From$80
Very good 4.5 /5 Recent Reviews Call BookMore Details
Wyndham Garden Dover Downtown in Dover
+1-888-897-9207

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New Reservations: +1-888-897-9207 Group Sales: +1-888-494-8863
561 North Dupont Highway, Dover, DE 19901 +1-888-897-9207 ~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.
  • 3 star Downtown hotel
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From$71
Average 3.0 /5 Reviews Call BookMore Details
Roost Baltimore - Baltimore
+1-888-311-4278

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New Reservations: +1-888-311-4278 Group Sales: +1-888-494-8863
2460 Terrapin Way, Baltimore, MD 21215 +1-888-311-4278 ~29.19 miles west of Chestertown
  • Pool in hotel: 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
+1-888-469-4795

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New Reservations: +1-888-469-4795 Group Sales: +1-888-494-8863
6323 Ritchie Highway, Glen Burnie, MD 21061 +1-888-469-4795 ~29.21 miles west of Chestertown
  • Pool details: 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 Hotel Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie - Glen Burnie
+1-888-734-9421

How should we direct your call?

New Reservations: +1-888-734-9421 Group Sales: +1-888-494-8863
6600 Ritchie Highway, Glen Burnie, MD 21061 +1-888-734-9421 ~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
  • Low priced Airport property
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From$57
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-841-5292

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New Reservations: +1-888-841-5292 Group Sales: +1-888-494-8863
8561 Ocean Gateway, Easton, MD 21601 +1-888-841-5292 ~29.32 miles south of Chestertown
  • Has swimming pool: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3-star Rural hotel
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From$115
Average 3.0 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites
+1-888-455-5160

How should we direct your call?

New Reservations: +1-888-455-5160 Group Sales: +1-888-494-8863
1 Center Dr., North East, MD 21901 +1-888-455-5160 ~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.
  • Mid-scale Rural hotel
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From$67
Average 3.0 /5 Recent Reviews Call BookMore Details
Tremont Plaza Hotel : 222 St. Paul Place
+1-888-965-8297

How should we direct your call?

New Reservations: +1-888-965-8297 Group Sales: +1-888-494-8863
222 St. Paul Place, Baltimore, MD 21202 +1-888-965-8297 ~29.52 miles west of Chestertown
  • Includes a 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.
  • 3 star Downtown hotel
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From$89
Very good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn
+1-888-906-6358

How should we direct your call?

New Reservations: +1-888-906-6358 Group Sales: +1-888-494-8863
8801 Loch Raven Blvd., Towson, MD 21286 +1-888-906-6358 ~29.62 miles west of Chestertown
  • Pool details: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • 2-star Suburban property
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From$56
Very good 4.0 /5 Recent Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore - Baltimore
+1-888-749-6785

How should we direct your call?

New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
550 Light St., Baltimore, MD 21202 +1-888-749-6785 ~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 Review Score Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor in Baltimore
+1-888-878-9982

How should we direct your call?

New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
131 East Redwood St., Baltimore, MD 21202 +1-888-878-9982 ~29.67 miles west of Chestertown
  • Pool details: 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.
  • Three Star Downtown hotel
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From$89
Very good 4.5 /5 Recent Reviews Call BookMore Details
The Royal Sonesta Harbor Court - 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 21230 +1-888-389-4485 ~29.68 miles west of Chestertown
  • Has swimming pool: Our rooftop indoor pool is open 5am-10pm daily
  • Expensive Downtown property
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From$125
Average 3.0 /5 Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor
+1-888-389-4121

How should we direct your call?

New Reservations: +1-888-389-4121 Group Sales: +1-888-494-8863
300 Light St., Baltimore, MD 21202 +1-888-389-4121 ~29.71 miles west of Chestertown
  • We have a pool
  • High end Convention Center hotel
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From$125
Average 3.0 /5 Read Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-888-675-2083

How should we direct your call?

New Reservations: +1-888-675-2083 Group Sales: +1-888-494-8863
173 Jennifer Rd., Annapolis, MD 21401 +1-888-675-2083 ~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. Hours vary.
  • Midscale Suburban property
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From$80
Very good 4.0 /5 Review Score Call BookMore Details
Home2 Suites by Hilton Dover De
+1-800-716-8490

How should we direct your call?

New Reservations: +1-800-716-8490 Group Sales: +1-888-494-8863
222 South Dupont Highway, Dover, DE 19901 +1-800-716-8490 ~29.76 miles east of Chestertown
  • Includes a pool: 6am - 10pm
  • Economy Downtown hotel
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From$99
Very good 4.0 /5 Reviews Call BookMore Details
Hampton Inn & Suites
+1-800-805-5223

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New Reservations: +1-800-805-5223 Group Sales: +1-888-494-8863
Hampton Inn 124, Annapolis, MD 21401 +1-800-805-5223 ~29.81 miles southwest of Chestertown
  • Has swimming pool: Seasonal outdoor pool
  • Midscale Highway hotel
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From$80
Average 3.0 /5 Latest Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor - Baltimore
+1-888-965-1860

How should we direct your call?

New Reservations: +1-888-965-1860 Group Sales: +1-888-494-8863
100 Hopkins Pl, Baltimore, MD 21201 +1-888-965-1860 ~29.93 miles west of Chestertown
  • Pool in hotel: Outdoor pool (seasonal)
  • Midscale Downtown property
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From$73
Very good 4.0 /5 Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-788-5576

How should we direct your call?

New Reservations: +1-888-788-5576 Group Sales: +1-888-494-8863
1100 Cromwell Bridge Rd., Towson, MD 21286 +1-888-788-5576 ~30.06 miles west of Chestertown
  • Includes a 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.
  • Affordable Suburban property
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From$69
Very good 4.0 /5 Read Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis - Annapolis
+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.
  • 3-star Suburban property
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From$149
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Annapolis : 2520 Riva Rd.
+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 in hotel: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Cheap Suburban hotel
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From$84
Average 3.0 /5 Hotel Reviews Call BookMore Details
Best Western Chesapeake Bay North Inn : 39 Elwoods Rd.
+1-888-469-4795

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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.
  • Mid-scale Rural property
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From$71
Very good 4.0 /5 Read Reviews Call BookMore Details
Hampton Inn & Suites Annapolis - Annapolis
+1-888-734-9421

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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.
  • 3-star Suburban hotel
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From$70
Very good 4.0 /5 Latest Reviews Call BookMore Details
Sonesta Es Suites Annapolis : 170 Admiral Cochrane Dr.
+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
  • Has swimming pool: Seasonal Outdoor Pool
  • Expensive Suburban hotel
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From$99
Very good 4.0 /5 Read Reviews Call BookMore Details
Best Western Galaxy Inn - Dover
+1-888-455-5160

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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 details: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Affordable 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

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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 in hotel: Indoor Pool 9 AM - 10 PM
  • Midscale Downtown hotel
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Sheraton Baltimore North : 903 Dulaney Valley Rd.
+1-888-906-6358

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903 Dulaney Valley Rd., Towson, MD 21204 +1-888-906-6358 ~31.54 miles west of Chestertown
  • Pool available: Hotel has an indoor pool. Pool is open from 7am -10pm.
  • Midscale Suburban hotel
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From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Days Inn by Wyndham Easton in Easton
+1-888-749-6785

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New Reservations: +1-888-749-6785 Group Sales: +1-888-494-8863
7018 Ocean Gateway, Easton, MD 21601 +1-888-749-6785 ~32.19 miles south of Chestertown
  • Has swimming pool: out door swimming pool
  • Midscale property
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From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Elkton : 2 Warner Rd.
+1-888-878-9982

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New Reservations: +1-888-878-9982 Group Sales: +1-888-494-8863
2 Warner Rd., Elkton, MD 21921 +1-888-878-9982 ~32.48 miles northeast of Chestertown
  • Has swimming pool: 9am- 10pm
  • Three Star Highway hotel
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From$119
Very good 4.0 /5 Recent Reviews Call BookMore Details
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