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

Find Hotels with a Pool in Sherwood, MD

  • 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 Hotels with a Pool

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 building with a sign reading "The Inn."
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.
₩204,788
₩225,267 total
includes taxes & fees
Sep 28 - Sep 29
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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
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.

2. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₩121,644
₩133,809 total
includes taxes & fees
Sep 30 - Oct 1
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.
A spacious indoor dining area with large windows, tables, and chairs.
A large building with a swimming pool, dock, and green surroundings.

3. The Tilghman Island Inn

The Tilghman Island Inn
Tilghman
  • Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
₩252,571
₩277,828 total
includes taxes & fees
Sep 27 - Sep 28
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.

4. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
  • Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
₩230,386
₩321,688 total
includes taxes & fees
Sep 27 - Sep 28
Wylder Tilghman Island
A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and a building with columns.
A kitchen with a stone wall, a microwave, and various food items on the counter.
A residential area with a large building, a swimming pool, and well-maintained lawns.

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 center.
₩121,657
₩133,822 total
includes taxes & fees
Oct 1 - Oct 2
Baymont by Wyndham Easton
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a bathtub, toilet, and shower.
A hotel room with a bed, desk, chair, television, and a painting on the wall.

6. 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.
₩173,728
₩192,838 total
includes taxes & fees
Oct 1 - Oct 2
Best Western Kent Narrows Inn
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 staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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.
₩197,394
₩264,571 total
includes taxes & fees
Oct 7 - Oct 8
Rod 'N' Reel Resort
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.
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.

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.
₩140,695
₩156,172 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Annapolis East-Kent Island by IHG
A hotel pool area with multiple pools, lounge chairs, and a pool lift.
A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.
A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.
A hotel lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

9. 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.
₩176,117
₩193,729 total
includes taxes & fees
Sep 27 - Sep 28
Best Western Plus Easton Inn & Suites
A spacious lobby with a staircase, a reception desk, and a dining area.
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.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

10. 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.
₩136,597
₩151,623 total
includes taxes & fees
Oct 18 - Oct 19
Quality Inn Grasonville near Kent Island
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Staff is extremely friendly and welcoming"
Richard 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"I didn’t really like the casino vibe. But I’m sure it was just me."
Christine 1-night trip
Posted 7 hours ago
Rod 'N' Reel Resort
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 3 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 3 days 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 3 days ago
Courtyard by Marriott 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.

Explore a world of travel with Expedia