Chestertown Hotels with Outdoor or Indoor Pools
Best Western Kent Narrows Inn
+1-800-716-8490
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 hotel
Holiday Inn Express Aberdeen, an IHG Hotel in Aberdeen
+1-888-469-4795
1007 Beards Hill Rd., Aberdeen, MD 21001
+1-888-469-4795
~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.
- Affordable Highway hotel
Hampton Inn Baltimore/White Marsh - Nottingham
+1-888-965-8297
8225 Town Center Dr., Nottingham, MD 21236
+1-888-965-8297
~23.79 miles west of Chestertown
- Has swimming pool: Outdoor Pool Opened Seasonally Memorial Day thru Labor Day. Beautiful patio with Fire Pit available for guests to use.
- Midscale Suburban property
The Westin Annapolis
+1-800-716-8490
100 Westgate Cir, Annapolis, MD 21401
+1-800-716-8490
~28.40 miles southwest of Chestertown
- Includes a pool: indoor pool. hours vary based upon season
- High end Downtown property
Wyndham Garden Dover Downtown
+1-888-311-4278
561 North Dupont Highway, Dover, DE 19901
+1-888-311-4278
~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
Roost Baltimore
+1-888-469-4795
2460 Terrapin Way, Baltimore, MD 21215
+1-888-469-4795
~29.19 miles west of Chestertown
- Has swimming pool: Outdoor open-air pool lined with cabanas open from 8am- Sun down.
- 4-star property
Red Roof Inn Baltimore South - Glen Burnie
+1-888-841-5292
6600 Ritchie Highway, Glen Burnie, MD 21061
+1-888-841-5292
~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
- Two star Airport hotel
Comfort Inn & Suites in North East
+1-888-965-8297
1 Center Dr., North East, MD 21901
+1-888-965-8297
~29.39 miles north of Chestertown
- Pool in hotel: 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 property
Tremont Plaza Hotel - Baltimore
+1-888-906-6358
222 St. Paul Place, Baltimore, MD 21202
+1-888-906-6358
~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.
- Midscale Downtown hotel
Comfort Inn : 8801 Loch Raven Blvd.
+1-888-749-6785
8801 Loch Raven Blvd., Towson, MD 21286
+1-888-749-6785
~29.62 miles west of Chestertown
- Pool available: Private and cozy Outdoor Pool, open Memorial Day to Labor day...12noon to 8 p.m.
- Cheap Suburban hotel
The Royal Sonesta Harbor Court Baltimore : 550 Light St.
+1-888-878-9982
550 Light St., Baltimore, MD 21202
+1-888-878-9982
~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
- 4 star Downtown hotel
Hampton Inn & Suites Baltimore Inner Harbor
+1-888-389-4485
131 East Redwood St., Baltimore, MD 21202
+1-888-389-4485
~29.67 miles west of Chestertown
- Pool available: 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.
- Midscale Downtown hotel
Crowne Plaza Annapolis An Ihg Hotel - Annapolis
+1-888-675-2083
173 Jennifer Rd., Annapolis, MD 21401
+1-888-675-2083
~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.
- Midscale Suburban hotel
Holiday Inn Express Towson Baltimore North An Ihg Hotel
+1-888-897-9207
1100 Cromwell Bridge Rd., Towson, MD 21286
+1-888-897-9207
~30.06 miles west of Chestertown
- Pool available: 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.
- Three Star Suburban property
Hilton Baltimore Inner Harbor
+1-888-311-4278
401 West Pratt St., Baltimore, MD 21201
+1-888-311-4278
~30.07 miles west of Chestertown
- Includes a pool: The Hilton Baltimore has a 30ft two lane track pool.
- 4 star Downtown property
Hilton Garden Inn Annapolis - Annapolis
+1-888-455-5160
305 Harry South Truman Pkwy., Annapolis, MD 21401
+1-888-455-5160
~30.53 miles southwest of Chestertown
- Pool available: We have an outdoor pool. We open it on Memorial Day and close it on Labor Day.
- Mid-scale property
Sonesta Es Suites Annapolis
+1-888-965-8297
170 Admiral Cochrane Dr., Annapolis, MD 21401
+1-888-965-8297
~30.57 miles southwest of Chestertown
- Includes a pool: Seasonal Outdoor Pool
- Four star Suburban property
Back to Top