A large brick house with a green roof, surrounded by lush gardens and trees.

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Check availability on Sherwood Hotels with Pool

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Sherwood hotels with a pool

A swimming pool with multiple people swimming and lounging around.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A covered patio area with wicker furniture and a view of a building with large windows.
A building with a sign reading "The Inn."

1. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
Rp1.788.200
Rp1.967.020 total
includes taxes & fees
1 Nov - 2 Nov
Knapps Narrows Marina & Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A large building with a swimming pool, dock, and green surroundings.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.
A modern lounge area with a fireplace, seating, and a view of the outdoors.

2. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
Rp3.308.170
Rp3.638.987 total
includes taxes & fees
6 Oct - 7 Oct
The Tilghman Island Inn
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A room with a view of a wooden deck and a gazebo by the water.
A white house with a garden patio featuring a wicker chair and a round table.

3. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
Rp9.173.466
Rp10.090.813 total
includes taxes & fees
3 Nov - 4 Nov
Inn at Perry Cabin
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront property with a covered patio, a dock, and a boat.
A waterfront hotel with a covered dock and a large building with multiple balconies.

4. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
Rp4.200.482
Rp5.514.630 total
includes taxes & fees
6 Oct - 7 Oct
Wylder Tilghman Island
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

5. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
Rp1.593.286
Rp1.752.616 total
includes taxes & fees
6 Oct - 7 Oct
St Michaels Inn
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.
A wooden console table with framed floral artwork, two lamps, and two ottomans.

6. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
Rp7.869.868
Rp8.656.855 total
includes taxes & fees
6 Oct - 7 Oct
The Oaks Waterfront
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A modern bar area with a long counter and multiple bar stools.

7. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
Rp2.585.469
Rp2.869.870 total
includes taxes & fees
20 Oct - 21 Oct
Rod 'N' Reel Resort
An indoor swimming pool with a 'NO LIFEGUARD ON DUTY' sign, lounge chairs, and potted plants.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A bathroom with a toilet, a sink, and a mirror. There are towels on a rack above the toilet and a towel on the sink counter.
A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

8. Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
Easton
  • Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.
Rp2.396.188
Rp2.635.807 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Easton by IHG
A two-story house with a swimming pool, outdoor seating, and a covered patio area.
A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.
A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.
A two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

9. George Brooks House B&B

George Brooks House B&B
St. Michaels
  • Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
Rp3.460.167
Rp3.806.184 total
includes taxes & fees
2 Nov - 3 Nov
George Brooks House B&B
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.
A hotel with a covered entrance, multiple floors, and a parking lot.
A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

10. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
Rp2.416.752
Rp2.658.427 total
includes taxes & fees
25 Oct - 26 Oct
Fairfield Inn & Suites by Marriott Easton
View all properties

Choose what matters most at hotels with a pool in Sherwood

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Sherwood Hotel Reviews

Best Western Annapolis

Best Western Annapolis

8/10 Good
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
Silvia 1-night trip
Posted 10 hours ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 15 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 4 days ago
St Michaels Inn
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

10/10 Excellent
"I will be back! Beautiful surroundings in a very well maintained, locally staffed (and guessing owned in conjunction with the marina), quaint hotel. The sound of the moored boats out front was soothing and the place was spic and span. Front desk staff are very friendly and great with recommendations."
Bonnie 3-night trip
Posted 7 days ago
Knapps Narrows Marina & Inn
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 2 weeks ago
The Westin Annapolis

Frequently asked questions

What are some accommodation options with pools in Sherwood?
Knapps Narrows Marina & Inn: Hotel, 14-minute walk from Chesapeake Bay. Features daily, a seasonal outdoor pool and free self parking. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool and 2 restaurants. Crowne Plaza Annapolis by IHG: Offers daily, a seasonal outdoor pool and free self parking. Graduate by Hilton Annapolis: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access.
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 with an outdoor swimming pool if you're planning to visit Sherwood in the warmest months of July, August or June, when the average temperature is 24°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temperature is 5°C.

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