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

Hotels with Swimming Pool in Sherwood, Maryland

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Check availability on Sherwood Hotels with Swimming Pool

Tonight
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Sherwood hotels with a pool

A swimming pool with multiple people swimming and lounging around.
A covered patio area with wicker furniture and a view of a building with large windows.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.
A waterfront property with houses, a dock, and a grassy area.

1. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
P6,280
P6,908 total
includes taxes & fees
Nov 1 - Nov 2
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.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

2. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
P11,618
P12,780 total
includes taxes & fees
Oct 5 - Oct 6
The Tilghman Island Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A waterfront hotel with a covered dock and a large building with multiple balconies.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.

3. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
P13,734
P18,248 total
includes taxes & fees
Oct 18 - Oct 19
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 conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
P5,595
P6,155 total
includes taxes & fees
Oct 4 - Oct 5
St Michaels Inn
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A bedroom with a large bed, a wooden chair, a balcony with white curtains, and a view of greenery.
A white house with a garden patio featuring a wicker chair and a round table.
A golf course with a water hazard and surrounding trees.

5. 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.
P32,216
P35,438 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
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 hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.
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.

6. 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.
P8,415
P9,257 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Easton by IHG
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
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.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
  • Scenic waterfront pool creates a summer paradise with views and easy water access.
P27,529
P30,282 total
includes taxes & fees
Oct 4 - Oct 5
The Oaks Waterfront
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

8. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
P8,101
P8,911 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Plus Easton Inn & Suites
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

9. 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.
P9,080
P12,170 total
includes taxes & fees
Oct 8 - Oct 9
Rod 'N' Reel Resort
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 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.
A hotel with a covered entrance, multiple floors, and a parking lot.

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.
P8,487
P9,336 total
includes taxes & fees
Oct 11 - Oct 12
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great hotel staff"
Humberto 1-night trip
Posted 5 hours ago
Graduate by Hilton Annapolis
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Everything was fine. I came back very late at night and found my key wouldn't work but the desk person got it straightened out with no problem at all."
Benjamin 2-night trip
Posted 6 hours ago
Best Western Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 1 day ago
St Michaels Inn
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Had a good time. Nice area"
Thomas E 3-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina
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 4 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 11 days ago
The Westin Annapolis

Frequently asked questions

What are some accommodations 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 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.

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