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Chestertown Hotels with Outdoor or Indoor Pools

Quality Inn
+1-888-389-4121
101 Vfw Ave., Grasonville, MD 21638 ~18.54 miles southwest of Chestertown
  • We have a pool
  • Economical Resort property
From$74
Very Good 4.0 /5 Reviews Call BookMore Details
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Holiday Inn Express Annapolis East-Kent Island by IHG
+1-888-675-2083
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Pool available: Outdoor pool open from Memorial day to labor day 9am-9pm
  • Three Star Rural hotel
From$180
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Kent Narrows Inn - Grasonville
+1-800-716-8490
3101 Main St., Grasonville, MD 21638 ~19.04 miles southwest of Chestertown
  • Pool in hotel: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • Three Star Resort hotel
From$80
Average 3.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Kent Island Marina
+1-800-805-5223
3206 Main St., Grasonville, MD 21638 ~19.08 miles southwest of Chestertown
  • Includes a pool: Indoor pool open daily 5 AM-11PM
  • Three Star Riverfront property
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
1326 Policy Dr., Belcamp, MD 21017 ~20.96 miles northwest of Chestertown
  • Pool in hotel: Indoor Heated Pool. Open from 9am - 10pm daily.
  • Three Star Suburban property
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
1807 Edgewood Rd., Edgewood, MD 21040 ~21.05 miles northwest of Chestertown
  • Has a pool!
  • 3 star Suburban property
From$54
Average 3.0 /5 Read Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen
+1-888-897-9207
1357 Belcamp Rd., Belcamp, MD 21017 ~21.21 miles northwest of Chestertown
  • Pool available: Our indoor heated pool is open from 7 am to 10 pm.
  • Midscale Rural hotel
From$89
Average 3.0 /5 Recent Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South : 2110 Emmorton Park Rd.
+1-888-311-4278
2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.33 miles northwest of Chestertown
  • Has swimming pool: Indoor Pool available 6AM to 10PM
  • Affordable Suburban property
From$95
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Aberdeen
+1-888-469-4795
1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.48 miles north of Chestertown
  • Pool available: FREE INDOOR W/ HOT TUB
  • Mid-scale Suburban property
From$110
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Holiday Inn Express Aberdeen by IHG : 1007 Beards Hill Rd.
+1-888-734-9421
1007 Beards Hill Rd., Aberdeen, MD 21001 ~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.
  • Mid-scale Highway property
From$147
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore / Aberdeen
+1-888-841-5292
795 West Bel Air Ave., Aberdeen, MD 21001 ~22.63 miles north of Chestertown
  • Pool in hotel: Indoor pool
  • Cheap Highway property
From$89
Very Good 4.5 /5 Read Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen Near Apg : 980 Hospitality Way
+1-888-455-5160
980 Hospitality Way, Aberdeen, MD 21001 ~22.75 miles north of Chestertown
  • Pool available: Seasonal Large Outdoor Pool with picnic tables and grills
  • 3-star Highway hotel
From$84
Average 3.0 /5 Reviews Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh
+1-888-965-8297
5015 Campbell Blvd., Baltimore, MD 21236 ~23.76 miles west of Chestertown
  • Pool details: Indoor Pool
  • Midscale Suburban property
From$89
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn Baltimore/White Marsh
+1-888-906-6358
8225 Town Center Dr., Nottingham, MD 21236 ~23.79 miles west of Chestertown
  • Pool details: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • Affordable Suburban hotel
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Country Inn & Suites by Radisson Baltimore North Md
+1-888-749-6785
8825 Yellow Brick Rd., Rosedale, MD 21237 ~23.90 miles west of Chestertown
  • Pool available: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • 3 star Suburban hotel
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
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Fairfield Inn & Suites by Marriott White Marsh
+1-888-878-9982
8477 Cordon Way, Baltimore, MD 21236 ~23.93 miles west of Chestertown
  • Includes a pool: Seasonal Outdoor Pool opens Memorial Day weekend and closed Labor Day weekend.
  • Mid-scale Suburban property
From$89
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Best Western Denton Inn in Denton
+1-888-389-4485
521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • Includes a pool
  • 3 star Highway hotel
From$68
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Best Western Plus Hotel & Conference Center
+1-888-389-4121
5625 O'donnell St., Baltimore, MD 21224 ~26.13 miles west of Chestertown
  • Pool in hotel: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Midscale Highway hotel
From$72
Average 3.0 /5 Read Reviews Call BookMore Details
Hilton Garden Inn Dover
+1-888-675-2083
1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Pool details: Pool open daily form 8am-10pm.
  • 3 star Suburban property
From$84
Very Good 4.5 /5 Review Score Call BookMore Details
The Westin Annapolis
+1-800-716-8490
100 Westgate Cir, Annapolis, MD 21401 ~28.40 miles southwest of Chestertown
  • Includes a pool: indoor pool. hours vary based upon season
  • High-end Downtown property
From$139
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Comfort Inn & Suites - Dover
+1-800-805-5223
764 Dover Leipsic Rd., Dover, DE 19901 ~28.78 miles east of Chestertown
  • Includes a pool
  • Affordable Suburban hotel
From$83
Very Good 4.5 /5 Recent Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor in Baltimore
+1-888-965-1860
511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Includes a pool: INDOOR POOL
  • Midscale Downtown property
From$85
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor in Baltimore
+1-888-788-5576
625b South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Has a pool!
  • Mid-scale Downtown hotel
From$110
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore
+1-888-897-9207
625a South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • We have a pool
  • Affordable Downtown hotel
From$80
Very Good 4.5 /5 Read Reviews Call BookMore Details
Residence Inn Dover - Dover
+1-888-311-4278
600 Jefferic Blvd., Dover, DE 19901 ~29.10 miles east of Chestertown
  • Pool in hotel
  • Four star Suburban property
From$125
Average 3.0 /5 Review Score Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-469-4795
561 North Dupont Highway, Dover, DE 19901 ~29.11 miles east of Chestertown
  • Includes a pool: We have an outdoor seasonal pool. Open daily 9:00am to 9:00pm Memorial Day to Labor Day.
  • 3 star Downtown property
From$71
Average 3.0 /5 Guest Reviews Call BookMore Details
Roost Baltimore in Baltimore
+1-888-734-9421
2460 Terrapin Way, Baltimore, MD 21215 ~29.19 miles west of Chestertown
  • Pool details: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
  • Expensive property
From$129
Average 3.0 /5 Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie
+1-888-841-5292
6323 Ritchie Highway, Glen Burnie, MD 21061 ~29.21 miles west of Chestertown
  • Pool available: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • Three Star Suburban hotel
From$75
Average 3.0 /5 Guest Reviews Call BookMore Details
Red Roof Inn Baltimore South - Glen Burnie : 6600 Ritchie Highway
+1-888-455-5160
6600 Ritchie Highway, Glen Burnie, MD 21061 ~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
  • Inexpensive Airport hotel
From$57
Average 3.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-965-8297
8561 Ocean Gateway, Easton, MD 21601 ~29.32 miles south of Chestertown
  • Pool details: Indoor Pool & Whirlpool 9:00am-10:00pm
  • Three Star Rural property
From$115
Average 3.0 /5 Review Score Call BookMore Details
Quality Inn
+1-888-906-6358
8523 Ocean Gateway, Easton, MD 21601 ~29.37 miles south of Chestertown
  • Includes a pool: 9:00am-9:00pm Outdoor Pool
  • Economical Rural hotel
From$79
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-888-749-6785
1 Center Dr., North East, MD 21901 ~29.39 miles north of Chestertown
  • Has swimming pool: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • 3 star Rural property
From$67
Average 3.0 /5 Review Score Call BookMore Details
Comfort Inn in Towson
+1-888-878-9982
8801 Loch Raven Blvd., Towson, MD 21286 ~29.62 miles west of Chestertown
  • Includes a pool: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Economy Suburban property
From$56
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore
+1-888-389-4485
550 Light St., Baltimore, MD 21202 ~29.64 miles west of Chestertown
  • Includes a 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
  • Expensive Downtown hotel
From$79
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor
+1-888-389-4121
131 East Redwood St., Baltimore, MD 21202 ~29.67 miles west of Chestertown
  • Includes a 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 property
From$89
Very Good 4.5 /5 Latest Reviews Call BookMore Details
The Royal Sonesta Harbor Court in Baltimore
+1-888-675-2083
550 Light St., Baltimore, MD 21230 ~29.68 miles west of Chestertown
  • Pool available: Our rooftop indoor pool is open 5am-10pm daily
  • Four-star Downtown hotel
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
Hyatt Regency Baltimore Inner Harbor in Baltimore
+1-800-716-8490
300 Light St., Baltimore, MD 21202 ~29.71 miles west of Chestertown
  • Has swimming pool
  • Expensive Convention Center property
From$125
Average 3.0 /5 Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-800-805-5223
173 Jennifer Rd., Annapolis, MD 21401 ~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.
  • 3-star Suburban property
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Home2 Suites by Hilton Dover De - Dover
+1-888-965-1860
222 South Dupont Highway, Dover, DE 19901 ~29.76 miles east of Chestertown
  • Pool details: 6am - 10pm
  • Two star Downtown property
From$99
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites in Annapolis
+1-888-788-5576
Hampton Inn 124, Annapolis, MD 21401 ~29.81 miles southwest of Chestertown
  • Pool details: Seasonal outdoor pool
  • Midscale Highway property
From$80
Average 3.0 /5 Review Score Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor
+1-888-897-9207
100 Hopkins Pl, Baltimore, MD 21201 ~29.93 miles west of Chestertown
  • Has swimming pool: Outdoor pool (seasonal)
  • Mid-scale Downtown property
From$73
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-311-4278
1100 Cromwell Bridge Rd., Towson, MD 21286 ~30.06 miles west of Chestertown
  • Pool details: Our outdoor pool is open Memorial day to Labor day 10am-8pm. Life guard is always on duty. The pool is maximum 6 ft deep and has handicap lift.
  • Midscale Suburban property
From$69
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Doubletree by Hilton Hotel Annapolis : 210 Holiday Court
+1-888-469-4795
210 Holiday Court, Annapolis, MD 21401 ~30.10 miles southwest of Chestertown
  • Includes a pool: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Affordable Suburban hotel
From$149
Average 3.0 /5 Review Score Call BookMore Details
Best Western Annapolis - Annapolis
+1-888-734-9421
2520 Riva Rd., Annapolis, MD 21401 ~30.17 miles southwest of Chestertown
  • Pool in hotel: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Cheap Suburban property
From$84
Average 3.0 /5 Reviews Call BookMore Details
Wingate by Wyndham North East - North East
+1-888-841-5292
39 Elwoods Rd., North East, MD 21901 ~30.29 miles north of Chestertown
  • Pool in hotel: Indoor pool and hot tub open from 9:00am until 10:00pm. All minors must be accompanied by an adult.
  • Three Star Rural hotel
From$71
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Annapolis : 124 Womack Dr.
+1-888-455-5160
124 Womack Dr., Annapolis, MD 21401 ~30.39 miles southwest of Chestertown
  • Pool in hotel: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • 3 star Suburban hotel
From$70
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Sonesta Es Suites Annapolis : 170 Admiral Cochrane Dr.
+1-888-965-8297
170 Admiral Cochrane Dr., Annapolis, MD 21401 ~30.57 miles southwest of Chestertown
  • Pool details: Seasonal Outdoor Pool
  • Affordable Suburban property
From$99
Very Good 4.0 /5 Review Score Call BookMore Details
Best Western Galaxy Inn
+1-888-906-6358
1700 East Lebanon Rd., Dover, DE 19901 ~31.11 miles east of Chestertown
  • Has swimming pool: Seasonal outdoor pool. Open from May through September. 12am to 9:00pm.
  • Midscale Suburban property
From$70
Average 3.5 /5 Guest Reviews Call BookMore Details
Hampton / Home2 Suites Towson
+1-888-749-6785
21 West Susquehanna Ave., Towson, MD 21204 ~31.53 miles west of Chestertown
  • Pool available: Indoor Pool 9 AM - 10 PM
  • Midscale Downtown hotel
From$80
Average 3.0 /5 Recent Reviews Call BookMore Details
Sheraton Baltimore North
+1-888-878-9982
903 Dulaney Valley Rd., Towson, MD 21204 ~31.54 miles west of Chestertown
  • Has swimming pool: Hotel has an indoor pool. Pool is open from 7am -10pm.
  • Mid-scale Suburban hotel
From$80
Average 3.0 /5 Review Score Call BookMore Details

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