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

Sherwood Hotel Guide - Hotels with Pool in Sherwood, Maryland

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Check availability on Sherwood Hotels with Pool

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 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 building with a sign reading "The Inn."
A covered patio area with wicker furniture and a view of a building with large windows.
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.
€98
includes taxes & fees
5 Nov - 6 Nov
Knapps Narrows Marina & Inn
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
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.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
€87
includes taxes & fees
12 Oct - 13 Oct
St Michaels Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A spacious indoor dining area with large windows, tables, and chairs.
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.

3. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
€181
includes taxes & fees
12 Oct - 13 Oct
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 wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

4. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
€259
includes taxes & fees
18 Oct - 19 Oct
Wylder Tilghman Island
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.
A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.
A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

5. Baymont by Wyndham Easton

Baymont by Wyndham Easton
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
€87
includes taxes & fees
12 Oct - 13 Oct
Baymont by Wyndham Easton
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A modern bar area with a long counter and multiple bar stools.
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.

6. 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.
€143
includes taxes & fees
28 Oct - 29 Oct
Rod 'N' Reel Resort
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

7. 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.
€126
includes taxes & fees
13 Oct - 14 Oct
Best Western Plus Easton Inn & Suites
A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
Two Adirondack chairs facing a calm body of water with a clear sky above.

8. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
€109
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A restaurant with a counter, seating area, and a clock on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A bathroom with a glass-enclosed shower, a white toilet, and a white sink.

9. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
€107
includes taxes & fees
13 Oct - 14 Oct
Best Western Kent Narrows Inn
A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.
A four-poster bed with a floral bedspread, a nightstand with a lamp, and a chair with a cushion.
A bathroom with a toilet, sink, and window with curtains.
An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.

10. Parsonage Inn

Parsonage Inn
Downtown St. Michaels
  • Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.
€245
includes taxes & fees
2 Nov - 3 Nov
Parsonage Inn
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Choose what matters most at hotels with a pool in Sherwood

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"This was a nice spot to land while we visited Annapolis family and friends. Comfortable and very nice staff - especially in the dining room!"
Virginia 2-night trip
Posted 7 hours ago
DoubleTree by Hilton Hotel Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The views were fantastic."
Kathleen K 6-night trip
Posted 7 hours ago
Rod 'N' Reel Resort
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 2 days 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 2 days 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 5 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 8 days ago
Knapps Narrows Marina & Inn

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.