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Hotel Name
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Sherwood Hotels with Outdoor or Indoor Pools

Knapp's Narrows Marina & Inn in Tilghman Island 6176 Tilghman Island Rd., Tilghman Island, MD 21671 ~1.15 miles south of Sherwood
  • We have a pool
  • Luxurious 5-star Oceanfront property
The Inn at Perry Cabin - St. Michael's
+1-800-230-4134
308 Watkins Lane, St. Michael's, MD 21663 ~6.31 miles northeast of Sherwood
  • Includes a pool
  • High-end Resort property
From$245
Very Good 4.5 /5Review Score Call
The Old Brick Inn - St. Michaels 401 South Talbot St., St. Michaels, MD 21663 ~6.46 miles east of Sherwood
  • Pool in hotel
  • Midscale Rural property
From$120
Very Good 4.0 /5Hotel Reviews Call
St. Michaels Inn 1228 South Talbot St., St. Michaels, MD 21663 ~6.53 miles east of Sherwood
  • Pool in hotel
  • Midscale Resort property
St. Michaels Harbour Inn Marina & Spa in St. Michaels 101 North Harbor Rd., St. Michaels, MD 21663 ~6.71 miles east of Sherwood
  • Pool in hotel
  • Affordable Resort hotel
Harbourtowne Golf Resort & Conference Center : 9784 Martingham Dr. 9784 Martingham Dr., Saint Michaels, MD 21663 ~7.61 miles northeast of Sherwood
  • Has swimming pool: May - SeptemberOlympic Size Outdoor Pool with Lifeguard
  • Midscale Riverfront hotel
The Inn at Herrington Harbour 7161 Lake Shore Dr., Rose Haven, MD 20714 ~11.52 miles west of Sherwood
  • With a pool!
  • Four star Beach property
Chesapeake Beach Resort & Spa in Chesapeake Beach
+1-888-690-5281
4165 Mears Ave., Chesapeake Beach, MD 20732 ~11.55 miles west of Sherwood
  • We have a pool
  • 3-star Beach property
From$130
Very Good 4.0 /5Hotel Reviews Call
Hampton Inn : 8058 Ocean Gateway 8058 Ocean Gateway, Easton, MD 21601 ~14.55 miles east of Sherwood
  • Includes a pool
  • Low priced Downtown property
From$129
Very Good 4.5 /5Recent Reviews Call
Holiday Inn Express Easton 8561 Ocean Gateway, Easton, MD 21601 ~14.78 miles east of Sherwood
  • Pool in hotel: Indoor Pool & Whirlpool9:00am-11:00pm
  • 3-star Downtown property
Comfort Inn Easton 8523 Ocean Gateway, Easton, MD 21601 ~14.80 miles east of Sherwood
  • Pool details: 9:00am-9:00pmOutdoor Pool
  • Two star Rural hotel
From$75
Very Good 4.0 /5Read Reviews Call
Best Western Plus Easton Inn - Easton 8708 Alicia Dr., Easton, MD 21601 ~14.90 miles east of Sherwood
  • Includes a pool: Indoor swimming pool & hot tub
  • Mid-scale hotel
From$107
Excellent 5.0 /5Reviews Call
Hilton Garden Inn Kent Island : 3206 Main St. 3206 Main St., Grasonville, MD 21638 ~16.58 miles north of Sherwood
  • Pool details: Indoor pool open daily 6 AM-10PM
  • Midscale Riverfront property
From$132
Very Good 4.5 /5Review Score Call
Best Western Kent Narrows Inn : 3101 Main St. 3101 Main St., Grasonville, MD 21638 ~16.62 miles north of Sherwood
  • Includes a pool: Indoor heated pool & jacuzzi open year around from 6am to 10pm.
  • Low Cost Resort property
The Westin Annapolis : 100 Westgate Cir 100 Westgate Cir, Annapolis, MD 21401 ~19.06 miles northwest of Sherwood
  • Includes a pool: indoor pool. lifeguard on duty. hours vary based upon season
  • Four-star Downtown property
From$109
Very Good 4.0 /5Recent Reviews Call
Holiday Inn Express Cambridge Md - Cambridge 2715 Ocean Gateway, Cambridge, MD 21613 ~19.13 miles southeast of Sherwood
  • We have a pool ready for use
  • Affordable Rural property
Hyatt Regency Chesapeake Bay : 100 Heron Blvd.
+1-800-997-5148
100 Heron Blvd., Cambridge, MD 21613 ~19.37 miles southeast of Sherwood
  • Pool in hotel
  • Expensive property
From$225
Very Good 4.0 /5Latest Reviews Call
Holiday Inn Express in Prince Frederick
+1-888-690-5247
355 Merrimac Court, Prince Frederick, MD 20678 ~19.68 miles southwest of Sherwood
  • Pool details: Indoor PoolHolds 10,000 gallonsHours are 5am to 9pm
  • 3 star property
Springhill Suites by Marriott Annapolis 189 Admiral Cochrane Dr., Annapolis, MD 21401 ~20.19 miles northwest of Sherwood
  • Pool details: Indoor Swimming Pool with WhirlpoolWeekdays: 5pm-10pmFridays: 3pm - 10pmWeekends: 10am - 10pmSummer: 10am - 10pm daily
  • 3 star Suburban hotel
Hampton Inn & Suites Annapolis 124 Womack Dr., Annapolis, MD 21401 ~20.26 miles northwest of Sherwood
  • Has swimming pool: Outdoor Seasonal pool open from Memorial Day to Labor Day.
  • Midscale Suburban property
From$87
Very Good 4.0 /5Review Score Call
Annapolis Courtyard by Marriott - Annapolis 2559 Riva Rd., Annapolis, MD 21401 ~20.46 miles northwest of Sherwood
  • We have a pool ready for use
  • Affordable Downtown property
Hilton Garden Inn Annapolis : 305 Harry South Truman 305 Harry South Truman, Annapolis, MD 21401 ~20.46 miles northwest of Sherwood
  • Pool available: We have an outdoor pool. We open it on Memorial Day and close it on Labor Day.
  • Three Star property
Best Western Annapolis 2520 Riva Rd., Annapolis, MD 21401 ~20.51 miles northwest of Sherwood
  • Includes a pool: Ourdoor Pool Open daily from Memorial Day to Labor Day.
  • 2 star Suburban property
Doubletree Hotel Annapolis : 210 Holiday Court 210 Holiday Court, Annapolis, MD 21401 ~20.55 miles northwest of Sherwood
  • Pool available: Olympic Size Seasonal Outdoor Pool (open from Memorial Day until Labor Day). Lifeguard on duty.
  • Mid-scale Suburban property
From$102
Very Good 4.0 /5Hotel Reviews Call
Crowne Plaza in Annapolis 173 Jennifer Rd., Annapolis, MD 21401 ~20.68 miles northwest of Sherwood
  • Pool available: Heated indoor pool; glass doors open all around in summer to make it an outdoor area. Sun deck area. Also large whirlpool tht seats 10. Hours vary based on MD laws that require a lifeguard on duty. Higher demand dates have longer hours.
  • 4-star Suburban hotel
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