Find Hotels with a Pool in Sherwood, MD

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Check availability on Sherwood Hotels with a Pool

Top Sherwood Hotels with a Pool

Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (351)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is ₩146,129
₩160,742 total
includes taxes & fees
Nov 11 - Nov 12
Knapps Narrows Marina & Inn
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (1004)
Sparkling waters beckon at dual pools, where cabanas offer shaded luxury beside the marina. Beyond refreshing dips, guests enjoy complimentary bicycles, kayaking adventures, and nearby beach access, creating a complete coastal escape.
The price is ₩144,207
₩189,296 total
includes taxes & fees
Nov 17 - Nov 18
Rod 'N' Reel Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
  • Pool loungers
8.2 out of 10, Very Good, (1006)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is ₩162,462
₩178,709 total
includes taxes & fees
Nov 11 - Nov 12
St Michaels Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (810)
Poolside relaxation awaits after exploring the city center at this welcoming hotel. Spacious, clean rooms provide comfort while friendly staff ensure exceptional service. Guests appreciate the quiet atmosphere, complimentary breakfast, and convenient amenities.
The price is ₩117,999
₩129,799 total
includes taxes & fees
Dec 7 - Dec 8
Quality Inn
Outdoor pool
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

3.0 star property
Annapolis
  • Outdoor pool
8.2 out of 10, Very Good, (1001)
Sparkling waters beckon at the well-maintained outdoor pool, a highlight praised by guests for its cleanliness and welcoming atmosphere. After swimming, visitors can energize at the 24-hour fitness center or dine at the Garden Grille and Bar.
The price is ₩104,643
₩119,292 total
includes taxes & fees
Nov 16 - Nov 17
Hilton Garden Inn Annapolis
Indoor pool
Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

2.5 star property
Prince Frederick
  • Indoor pool
  • Near the beach
8.8 out of 10, Excellent, (680)
Swimming enthusiasts savor the warm, inviting indoor pool, accessible from early morning until evening. Located near Calvert Cliffs State Park and Running Hare Vineyard, this spotless hotel earns consistent praise for its helpful staff and delicious breakfast variety.
The price is ₩150,513
₩183,290 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Inn Express Prince Frederick by IHG
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very Good, (1004)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travelers appreciate the nearby hiking trails while enjoying spotless accommodations with 49-inch TVs and refrigerators.
The price is ₩134,468
₩149,259 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Kent Narrows Inn
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
  • On private beach
8.8 out of 10, Excellent, (88)
Seasonal outdoor swimming beckons travelers from March through October at this waterfront haven. Complementing the pool, a private beach, sauna, and free bicycles create perfect relaxation opportunities along the river's edge.
The price is ₩221,261
₩307,684 total
includes taxes & fees
Dec 1 - Dec 2
Wylder Tilghman Island
Seasonal outdoor pool
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3.0 star property
Edgewater
  • Pool
  • Breakfast included
  • Pet friendly
  • Free WiFi
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (942)
Splashes of joy await at the seasonal outdoor pool, complemented by basketball and volleyball courts for active afternoons. This all-suite hotel balances recreation with comfort, featuring cozy fireplaces and fully equipped kitchens in spacious rooms.
The price is ₩121,287
₩138,268 total
includes taxes & fees
Nov 30 - Dec 1
Sonesta ES Suites Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
  • Indoor pool
8.8 out of 10, Excellent, (1005)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness center. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
The price is ₩135,900
₩154,926 total
includes taxes & fees
Dec 7 - Dec 8
Crowne Plaza Annapolis by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"The room was clean and had plenty of space. The staff was amazing. The young lady that checked me in was very kind and professional. The bartender was funny and very attentive to all the patrons. "
dana 1-night trip
Posted 4 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What are some accommodations with pools in Sherwood?
Historic Inns of Annapolis: Features sun loungers, a pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG: Features a snack bar/deli, an indoor pool, and free self parking. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.
What is there to see and do in Sherwood?
The picturesque setting of Goat Island showcases the area's natural beauty. Discover sights such as Knapp's Narrows Marina & Inn during your stay.
When is the best time to book a hotel with a pool in Sherwood?
You may want to think about a place to stay that has an outdoor pool if you're planning to visit Sherwood in the hottest months of July, August, or June when the average temperature is 75°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temperature is 41°F.