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Chestertown Hotels with Outdoor or Indoor Pools

Comfort Inn & Suites Chestertown
+1-888-389-4121
150 Scheeler Rd., Chestertown, MD 21620
  • Includes a pool: Outdoor seasonal pool. Open 8am-10pm
  • Affordable Suburban hotel
From$90
Very Good 4.0 /5 Read Reviews Call BookMore Details
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Holiday Inn Express Annapolis - Kent Island, an IHG Hotel : 1020 Kent Narrows Rd.
+1-888-675-2083
1020 Kent Narrows Rd., Grasonville, MD 21638 ~18.94 miles southwest of Chestertown
  • Pool details: Outdoor pool open from Memorial day to labor day 9am-9pm
  • Affordable Rural property
From$180
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Kent Narrows Inn
+1-800-716-8490
3101 Main St., Grasonville, MD 21638 ~19.04 miles southwest of Chestertown
  • Includes a pool: Indoor heated pool, sauna & jacuzzi open year around from 6am to 10pm.
  • 3-star Resort property
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Home2 Suites by Hilton Baltimore / Aberdeen Md
+1-800-805-5223
20 Newton Rd., Aberdeen, MD 21001 ~20.61 miles north of Chestertown
  • Includes a pool: **Pool is temporarily closed for extensive maintenance.
  • Low-priced Suburban property
From$60
Average 3.0 /5 Guest Reviews Call BookMore Details
Holiday Inn Belcamp Aberdeen Area An Ihg Hotel
+1-888-965-1860
1326 Policy Dr., Belcamp, MI 21017 ~20.96 miles northwest of Chestertown
  • Includes a pool: Indoor Heated Pool. Open from 9am - 10pm daily.
  • 3-star Suburban property
From$80
Average 3.0 /5 Guest Reviews Call BookMore Details
Towneplace Suites Edgewood Aberdeen - Belcamp
+1-888-788-5576
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.
  • High end Rural property
From$89
Average 3.0 /5 Review Score Call BookMore Details
SpringHill Suites by Marriott Edgewood/Aberdeen in Bel Air
+1-888-897-9207
1420 Handlir Dr., Bel Air, MD 21015 ~21.27 miles northwest of Chestertown
  • Our hotel comes with a pool
  • Mid-scale Highway property
From$106
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD : 1435 Handlir Dr.
+1-888-311-4278
1435 Handlir Dr., Bel Air, MD 21015 ~21.29 miles northwest of Chestertown
  • Includes a pool: Outdoor Pool, open Memorial Day - Labor Day
  • Midscale Rural hotel
From$79
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Hampton Inn & Suites Edgewood/Aberdeen-South - Edgewood
+1-888-469-4795
2110 Emmorton Park Rd., Edgewood, MD 21040 ~21.33 miles northwest of Chestertown
  • Pool details: Indoor Pool available 6AM to 10PM
  • Mid-scale Suburban property
From$95
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Hilton Garden Inn Aberdeen - Aberdeen
+1-888-734-9421
1050 Beards Hill Rd., Aberdeen, MD 21001 ~22.48 miles north of Chestertown
  • Includes a swimming pool
  • Affordable Suburban hotel
From$110
Very Good 4.0 /5 Review Score Call BookMore Details
Holiday Inn Express Aberdeen, an IHG Hotel
+1-888-841-5292
1007 Beards Hill Rd., Aberdeen, MD 21001 ~22.51 miles north of Chestertown
  • Pool details: 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
From$147
Very Good 4.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites Aberdeen near APG
+1-888-455-5160
980 Hospitality Way, Aberdeen, MD 21001 ~22.75 miles north of Chestertown
  • Has swimming pool: Seasonal Large Outdoor Pool with picnic tables and grills
  • 3-star Highway property
From$84
Average 3.0 /5 Review Score Call BookMore Details
Hilton Garden Inn Baltimore/White Marsh : 5015 Campbell Blvd.
+1-888-965-8297
5015 Campbell Blvd., Baltimore, MD 21236 ~23.76 miles west of Chestertown
  • Pool details: Indoor Pool
  • 3-star Suburban property
From$89
Average 3.0 /5 Hotel 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
  • Includes a pool: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
  • 3 star Suburban property
From$89
Very Good 4.0 /5 Reviews Call BookMore Details
Residence Inn by Marriott Baltimore White Marsh
+1-888-749-6785
4980 Mercantile Rd., Baltimore, MD 21236 ~23.86 miles west of Chestertown
  • Pool available: Seasonal Indoor Pool opens Memorial Day Weekend and closes Labor Day Weekend.
  • 3 star Suburban property
From$109
Average 3.0 /5 Reviews Call BookMore Details
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Country Inn & Suites by Radisson, Baltimore North, MD
+1-888-878-9982
8825 Yellow Brick Rd., Rosedale, MD 21237 ~23.90 miles west of Chestertown
  • Includes a pool: Indoor Pool hours: Sunday-Saturday 5pm-9pm
  • 3-star Suburban property
From$80
Average 3.0 /5 Reviews Call BookMore Details
Fairfield Inn & Suites by Marriott White Marsh : 8477 Cordon Way
+1-888-389-4485
8477 Cordon Way, Baltimore, MD 21236 ~23.93 miles west of Chestertown
  • Pool available: Seasonal Outdoor Pool opens Memorial Day and closed Labor Day
  • Midscale Suburban hotel
From$89
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Holiday Inn Exp Stes Middletown
+1-888-389-4121
315 Auto Park Dr., Middletown, DE 19709 ~24.19 miles northeast of Chestertown
  • Includes a pool: Indoor Pool, open year round
  • Midscale Suburban hotel
From$70
Very Good 4.5 /5 Hotel Reviews Call BookMore Details
Best Western Denton Inn : 521 Fleetwood Rd.
+1-888-675-2083
521 Fleetwood Rd., Denton, MD 21629 ~25.35 miles southeast of Chestertown
  • We have a pool ready for use
  • Affordable Highway property
From$67
Very Good 4.0 /5 Reviews Call BookMore Details
Hampton Inn Baltimore Bayview Campus : 6571 Eastern Ave.
+1-800-716-8490
6571 Eastern Ave., Baltimore, MD 21224 ~25.61 miles west of Chestertown
  • Has swimming pool: Indoor/Heated Pool Lifeguard on duty M-F 5pm - 10pm Sat/Sun 9am -10pm Summer Fri 12p-10p
  • Affordable Suburban hotel
From$89
Average 3.0 /5 Review Score Call BookMore Details
Best Western Plus Hotel & Conference Center
+1-800-805-5223
5625 O'donnell St., Baltimore, MD 21224 ~26.13 miles west of Chestertown
  • Includes a pool: Indoor heated pool Open 10 am - 10 pm, weekly.
  • Affordable Highway property
From$72
Average 3.0 /5 Recent Reviews Call BookMore Details
Hilton Garden Inn Dover : 1706 North Dupont Highway
+1-888-965-1860
1706 North Dupont Highway, Dover, DE 19901 ~27.40 miles east of Chestertown
  • Includes a pool: Pool open daily form 8am-10pm.
  • 3-star Suburban property
From$84
Very Good 4.5 /5 Guest Reviews Call BookMore Details
The Westin Annapolis : 100 Westgate Cir
+1-888-788-5576
100 Westgate Cir, Annapolis, MD 21401 ~28.40 miles southwest of Chestertown
  • Pool available: indoor pool. hours vary based upon season
  • 4 star Downtown property
From$139
Very Good 4.0 /5 Latest Reviews Call BookMore Details
Comfort Inn & Suites - Dover
+1-888-897-9207
764 Dover Leipsic Rd., Dover, DE 19901 ~28.78 miles east of Chestertown
  • Includes a swimming pool
  • Mid-scale Suburban hotel
From$83
Very Good 4.5 /5 Read Reviews Call BookMore Details
Hyatt Place Baltimore Inner Harbor - Baltimore
+1-888-311-4278
511 South Central Ave., Baltimore, MD 21202 ~28.89 miles west of Chestertown
  • Has swimming pool: INDOOR POOL
  • Midscale Downtown property
From$85
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Hilton Garden Inn Baltimore Inner Harbor - Baltimore
+1-888-469-4795
625 South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Includes a pool
  • Midscale Downtown hotel
From$110
Very Good 4.0 /5 Read Reviews Call BookMore Details
Homewood Suites by Hilton Baltimore Inner Harbor - Baltimore
+1-888-734-9421
625a South President St., Baltimore, MD 21202 ~29.09 miles west of Chestertown
  • Pool in hotel
  • Affordable Downtown property
From$80
Very Good 4.5 /5 Reviews Call BookMore Details
Baltimore Marriott Waterfront in Baltimore
+1-888-841-5292
700 Aliceanna St., Baltimore, MD 21202 ~29.10 miles west of Chestertown
  • We have a pool ready for use
  • Four-star Downtown hotel
From$150
Very Good 4.0 /5 Hotel Reviews Call BookMore Details
Wyndham Garden Dover Downtown
+1-888-455-5160
561 North Dupont Highway, Dover, DE 19901 ~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.
  • Midscale Downtown property
From$71
Average 3.0 /5 Read Reviews Call BookMore Details
Roost Baltimore : 2460 Terrapin Way
+1-888-965-8297
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.
  • Four star hotel
From$129
Average 3.0 /5 Read Reviews Call BookMore Details
La Quinta Inn & Suites by Wyndham Baltimore S. Glen Burnie in Glen Burnie
+1-888-906-6358
6323 Ritchie Highway, Glen Burnie, MD 21061 ~29.21 miles west of Chestertown
  • Pool details: Best Practices for Hotel Pools and Fitness Center in compliance with State Ordinances.
  • 3 star Suburban hotel
From$75
Average 3.0 /5 Read Reviews Call BookMore Details
Red Roof Inn Baltimore South Glen Burnie
+1-888-749-6785
6600 Ritchie Highway, Glen Burnie, MD 21061 ~29.23 miles west of Chestertown
  • Pool in hotel: 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 Hotel Reviews Call BookMore Details
Holiday Inn Express Easton
+1-888-878-9982
8561 Ocean Gateway, Easton, MD 21601 ~29.32 miles south of Chestertown
  • Pool details: Indoor Pool & Whirlpool 9:00am-10:00pm
  • 3-star Rural property
From$115
Average 3.0 /5 Reviews Call BookMore Details
Comfort Inn & Suites : 1 Center Dr.
+1-888-389-4485
1 Center Dr., North East, MD 21901 ~29.39 miles north of Chestertown
  • Pool details: Indoor heated pool and whirlpool-open year round and open daily until 11:00pm - also adjacent to the 24-hour fitness center.
  • Affordable Rural hotel
From$67
Average 3.0 /5 Read Reviews Call BookMore Details
Tremont Plaza Hotel : 222 St. Paul Place
+1-888-389-4121
222 St. Paul Place, Baltimore, MD 21202 ~29.52 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.
  • Mid-scale Downtown hotel
From$89
Very Good 4.0 /5 Read Reviews Call BookMore Details
Comfort Inn - Towson
+1-888-675-2083
8801 Loch Raven Blvd., Towson, MD 21286 ~29.62 miles west of Chestertown
  • Pool in hotel: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
  • Cheap Suburban property
From$56
Very Good 4.0 /5 Read Reviews Call BookMore Details
The Royal Sonesta Harbor Court Baltimore
+1-800-716-8490
550 Light St., Baltimore, MD 21202 ~29.64 miles west of Chestertown
  • Pool available: 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 Read Reviews Call BookMore Details
Hampton Inn & Suites Baltimore Inner Harbor : 131 East Redwood St.
+1-800-805-5223
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.
  • Affordable Downtown hotel
From$89
Very Good 4.5 /5 Review Score Call BookMore Details
Hyatt Regency Baltimore Inner Harbor : 300 Light St.
+1-888-965-1860
300 Light St., Baltimore, MD 21202 ~29.71 miles west of Chestertown
  • Includes a pool
  • Expensive Convention Center property
From$125
Average 3.0 /5 Recent Reviews Call BookMore Details
Crowne Plaza Annapolis An Ihg Hotel
+1-888-788-5576
173 Jennifer Rd., Annapolis, MD 21401 ~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. Also large whirlpool tht seats 6. Hours vary.
  • Mid-scale Suburban hotel
From$80
Very Good 4.0 /5 Review Score Call BookMore Details
Home2 Suites by Hilton Dover, DE
+1-888-897-9207
222 South Dupont Highway, Dover, DE 19901 ~29.76 miles east of Chestertown
  • Pool details: 6am - 10pm
  • Two-star Downtown hotel
From$99
Very Good 4.0 /5 Recent Reviews Call BookMore Details
Embassy Suites Baltimore Inner Harbor - Baltimore
+1-888-311-4278
222 Saint Paul Pl, Baltimore, MD 21202 ~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.
  • High end Downtown property
From$69
Average 3.0 /5 Guest Reviews Call BookMore Details
Hampton Inn & Suites in Annapolis
+1-888-469-4795
Hampton Inn 124, Annapolis, MD 21401 ~29.81 miles southwest of Chestertown
  • Pool available: Seasonal outdoor pool
  • 3 star Highway hotel
From$80
Average 3.0 /5 Read Reviews Call BookMore Details
Radisson Hotel Baltimore Downtown Inner Harbor
+1-888-734-9421
101 West Fayette St., Baltimore, MD 21201 ~29.90 miles west of Chestertown
  • Pool details: Come experience our seasonal Rooftop Outdoor Pool opens Memorial Day to Labor Day.
  • Mid-scale Downtown property
From$87
Poor 2.0 /5 Reviews Call BookMore Details
Days Inn by Wyndham Baltimore Inner Harbor : 100 Hopkins Pl
+1-888-841-5292
100 Hopkins Pl, Baltimore, MD 21201 ~29.93 miles west of Chestertown
  • Pool available: Outdoor pool (seasonal)
  • 3-star Downtown hotel
From$73
Very Good 4.0 /5 Read Reviews Call BookMore Details
Holiday Inn Express Towson Baltimore North An Ihg Hotel - Towson
+1-888-455-5160
1100 Cromwell Bridge Rd., Towson, MD 21286 ~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 hotel
From$69
Very Good 4.0 /5 Reviews Call BookMore Details
Hilton Baltimore Inner Harbor in Baltimore
+1-888-965-8297
401 West Pratt St., Baltimore, MD 21201 ~30.07 miles west of Chestertown
  • Has swimming pool: The Hilton Baltimore has a 30ft two lane track pool.
  • Four star Downtown property
From$99
Very Good 4.0 /5 Reviews Call BookMore Details
Best Western Annapolis
+1-888-906-6358
2520 Riva Rd., Annapolis, MD 21401 ~30.17 miles southwest of Chestertown
  • Pool available: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • Cheap Suburban hotel
From$84
Average 3.0 /5 Hotel Reviews Call BookMore Details
Hampton Inn Easton : 8058 Ocean Gateway
+1-888-749-6785
8058 Ocean Gateway, Easton, MD 21601 ~30.28 miles south of Chestertown
  • Pool details: Pool Hours 6am to 10pm
  • Low priced Downtown property
From$119
Very Good 4.0 /5 Guest Reviews Call BookMore Details
Best Western Chesapeake Bay North Inn
+1-888-878-9982
39 Elwoods Rd., North East, MD 21901 ~30.29 miles north of Chestertown
  • With a pool!
  • Mid-scale Rural hotel
From$71
Very Good 4.0 /5 Latest Reviews Call BookMore Details

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