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

Sherwood Hotel with Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sherwood Hotel with Pool

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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 waterfront property with houses, a dock, and a grassy area.
A marina with several boats docked, a building with multiple levels, and a calm water surface reflecting the structures.

1. Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
Sherwood
  • Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
HK$1,177
HK$1,294 total
includes taxes & fees
24 Sept - 25 Sept
Knapps Narrows Marina & 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.
A large building with a swimming pool, dock, and green surroundings.

2. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
HK$1,608
HK$1,769 total
includes taxes & fees
27 Sept - 28 Sept
The Tilghman Island Inn
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 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.

3. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
HK$1,324
HK$1,848 total
includes taxes & fees
24 Sept - 25 Sept
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 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.

4. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
HK$741
HK$815 total
includes taxes & fees
30 Sept - 1 Oct
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 room with a view of a wooden deck and a gazebo by the water.

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.
HK$4,730
HK$5,203 total
includes taxes & fees
13 Oct - 14 Oct
Inn at Perry Cabin
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 hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

6. 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.
HK$1,012
HK$1,113 total
includes taxes & fees
30 Sept - 1 Oct
Best Western Plus Easton Inn & Suites
A swimming pool with blue lounge chairs and a building with balconies in the background.
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."
A marina with docked boats, a picnic area, and a grassy lawn with a tree.

7. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
  • Pool paradise meets scenic marina views for a refreshing escape on the water.
HK$1,617
HK$1,843 total
includes taxes & fees
30 Sept - 1 Oct
Anchored Inn at Hidden Harbour Marina
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
HK$1,192
HK$1,323 total
includes taxes & fees
7 Oct - 8 Oct
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.
An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.
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.

9. 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.
HK$1,060
HK$1,166 total
includes taxes & fees
27 Sept - 28 Sept
Fairfield Inn & Suites by Marriott Easton
A swimming pool with a white fence, lounge chairs, and umbrellas.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

10. 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.
HK$894
HK$993 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"My North Tower King -Bay view room was very clean with modern furnishings and a beatiful balcony of the Bay. Unforunately, there was a refrigerator but there wasn't a micro wave in the room. The bathroom had a lovely shower, with modern fixtures with compatible for handicapped accessible persons but failed to have some of the basics, like hand/body soap and a bathroom ceiling fan necessary for clean, purified air in the bathroom and hotel room."
Vera 1-night trip
Posted 4 hours ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Very nice decor and bed was comfortable . Classy looking place ."
princess 2-night trip
Posted 5 hours ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"U"
Ron 1-night trip
Posted 10 hours ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"The property is located in an awesome location; convenient to shopping and restaurants. They do have a decent bar and restaurant in the hotel. The property was clean, parking was free and available, staff was great. We would definitely stay again."
Randall 4-night trip
Posted 12 hours ago
DoubleTree by Hilton Hotel Annapolis
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."
William 1-night trip
Posted 1 day ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 1 day ago
The Westin Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"I thought breakfast was included but apparently not . There was not even complimentary coffee"
Gerald 2-night trip
Posted 1 day ago
Courtyard by Marriott Annapolis
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"No free breakfast but the one I had to pay for was good"
Darlene 1-night trip
Posted 4 days ago
Hilton Garden Inn Kent Island Marina

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.

Explore a world of travel with Expedia