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

Hotels with Swimming Pools in Sherwood

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Check availability on Sherwood Hotels with Swimming Pools

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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 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.
S$209
includes taxes & fees
25 Aug - 26 Aug
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 restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
S$117
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn
A swimming pool with a wooden deck, lounge chairs, and a fenced area.
A modern lounge area with a fireplace, seating, and a view of the outdoors.
An outdoor bar area with a view of the lake, wooden deck, and metal roof structure.
A spacious indoor dining area with large windows, tables, and chairs.

3. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
S$286
includes taxes & fees
25 Aug - 26 Aug
The Tilghman Island Inn
A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
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 gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

4. 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.
S$181
includes taxes & fees
3 Sept - 4 Sept
Rod 'N' Reel Resort
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 view through a window with a white railing, overlooking a marina with boats docked and a pier extending into the water.

5. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
S$371
includes taxes & fees
3 Sept - 4 Sept
Wylder Tilghman Island
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
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.
A buffet with labeled containers of omelets and other dishes.

6. 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.
S$179
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
A swimming pool with lounge chairs and a covered area, surrounded by a fence and buildings.
A lobby with a brick wall, three framed pictures, and a patterned carpet.
A modern building with large windows, a brick facade, and a well-maintained lawn with flower beds.
A hotel reception area with a wooden counter, a large sailboat painting, and a waffle station.

7. Quality Inn

Quality Inn
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
S$145
includes taxes & fees
27 Aug - 28 Aug
Quality Inn
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
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.
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.

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.
S$194
includes taxes & fees
25 Aug - 26 Aug
Best Western Plus Easton Inn & Suites
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
S$142
includes taxes & fees
14 Sept - 15 Sept
Quality Inn Grasonville near Kent Island
A swimming pool with a mural, lounge chairs, and a hot tub.
A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.
A modern interior with a dining area, kitchen, and living space.

10. 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.
S$179
includes taxes & fees
31 Aug - 1 Sept
Best Western Kent Narrows Inn
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Room was clean, staff was great. They should have notified in advance or had on line about all the construction and pool being closed."
Rick 1-night trip
Posted 2 hours ago
St Michaels Inn
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"."
Janice 3-night trip
Posted 6 hours ago
Rod 'N' Reel Resort
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 1 day ago
Courtyard by Marriott Annapolis
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future."
Annette 2-night trip
Posted 4 days ago
Hyatt Regency Chesapeake Bay
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

10/10 Excellent
"We enjoyed the peaceful garden and view from the balcony. The pool was great…we had it to ourselves late afternoon. The continental breakfast was very nice."
Jamie M 2-night trip
Posted 5 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. Offers 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. Rod 'N' Reel Resort: Features 2 outdoor swimming pools, a children's pool and a private beach.
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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