Pet-friendly Hotels in Sherwood

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Oct 18 - Oct 19

Tomorrow

Oct 19 - Oct 20

Next weekend

Oct 23 - Oct 25

In two weeks

Pet-friendly Hotels in Sherwood

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Sherwood on Hotels.com. These Sherwood Pet-friendly Hotels consistently deliver on quality, location and traveler experience. Last updated on October 17, 2026.

An outdoor seating area with tables and chairs, overlooking a body of water and greenery.

A waterfront property with a dock, a sailboat, and a building with a red roof.

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.

1. The Tilghman Island Inn

Tilghman

CNY1,237

CNY1,361 total

includes taxes & fees

Oct 19 - Oct 20

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.

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.

2. Wylder Tilghman Island

Tilghman

CNY1,571

CNY2,062 total

includes taxes & fees

Oct 19 - Oct 20

A two-story house with a porch, a front door, and a small garden area.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

3. The Wildset

Downtown St. Michaels

CNY1,531

CNY1,851 total

includes taxes & fees

Nov 3 - Nov 4

A room with a view of a wooden deck and a gazebo by the water.

A golf course with a water hazard and surrounding trees.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

4. Inn at Perry Cabin

Downtown St. Michaels

CNY3,282

CNY3,611 total

includes taxes & fees

Nov 18 - Nov 19

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

A living room with a fireplace, a sofa, a chair, and a bookshelf.

A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.

5. George Brooks House B&B

St. Michaels

CNY1,294

CNY1,423 total

includes taxes & fees

Nov 2 - Nov 3

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

A cozy room with a round table, a chair with a floral cushion, a lamp, a remote control, and a door.

An outdoor patio with a round wooden table and chairs, surrounded by potted plants and a brick wall.

A cozy room with a fireplace, a framed picture above it, and two armchairs.

6. Parsonage Inn

Downtown St. Michaels

CNY1,672

CNY1,839 total

includes taxes & fees

Nov 2 - Nov 3

A multi-story hotel with a central entrance, a landscaped garden with flowers, and a metal sculpture.

A modern kitchen with a large island, bar stools, and a wine rack.

A marina with docked boats, a picnic area, and a grassy lawn with a tree.

A modern kitchen with a bar area, wooden flooring, and blue bar stools.

7. Anchored Inn at Hidden Harbour Marina

Deale

CNY1,240

CNY1,414 total

includes taxes & fees

Oct 19 - Oct 20

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

Marina

8. Hyatt Place Kent Narrows & Marina

Grasonville

CNY1,016

CNY1,128 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

9. Hampton Inn Easton

Easton

CNY855

CNY941 total

includes taxes & fees

Oct 29 - Oct 30

A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.

A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.

A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.

A bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.

10. Hummingbird Inn

Easton

CNY1,980

CNY2,254 total

includes taxes & fees

Oct 19 - Oct 20

Two Adirondack chairs facing a calm body of water with a clear sky above.

A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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.

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

Grasonville

CNY662

CNY735 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

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 swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

12. Baymont by Wyndham Easton

Easton

CNY596

CNY655 total

includes taxes & fees

Oct 21 - Oct 22

A hot tub in a grassy area with a building in the background.

A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

A pool with two Adirondack chairs and a basket of items on the grass.

A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

13. The Inn at Tacaro Estate

Tracys Landing

CNY2,339

CNY2,667 total

includes taxes & fees

Nov 1 - Nov 2

A patio with outdoor seating, overlooking a marina with boats.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

14. Hilton Garden Inn Kent Island Marina

Grasonville

CNY839

CNY931 total

includes taxes & fees

Nov 18 - Nov 19

A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

A reception desk with a clock, framed pictures, and a sign for express checkout.

Exterior

A restaurant with a counter, seating area, and a clock on the wall.

15. Best Western Kent Narrows Inn

Grasonville

CNY601

CNY667 total

includes taxes & fees

Nov 8 - Nov 9

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

A store with shelves of beverages, a counter with a cash register, and baskets with items.

16. The Westin Annapolis

Annapolis

CNY1,331

CNY1,517 total

includes taxes & fees

Oct 25 - Oct 26

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

A spacious indoor area with brick walls, multiple tables and chairs, and string lights.

A marina with multiple boats docked during sunset.

A historic brick building with a red roof, multiple windows, and a central staircase.

17. Historic Inns of Annapolis

Historic District

CNY573

CNY882 total

includes taxes & fees

Oct 30 - Oct 31

A hotel lobby with a reception desk, a large aquarium, and framed artwork on the walls.

A modern living room with a sofa, armchairs, a coffee table, and a fireplace.

A DoubleTree by Hilton hotel entrance with a brick facade, a gated driveway, and a clear sky.

A restaurant with wooden tables and chairs, a bar area, and a tiled floor.

18. DoubleTree by Hilton Hotel Annapolis

Annapolis

CNY740

CNY844 total

includes taxes & fees

Oct 20 - Oct 21

An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.

A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.

A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.

A marina with boats docked, a sandy beach, and a clear blue sky.

19. Hyatt Regency Chesapeake Bay

Cambridge

CNY1,036

CNY1,367 total

includes taxes & fees

Nov 18 - Nov 19

A marina with numerous boats docked, a prominent building with a dome in the background, and a clear view of the water.

A modern lounge area with a blue sofa, red chairs, and plaid armchairs. A coffee table with books and a vase of flowers is in the center. Large windows offer a view of a brick building with awnings.

A bar with a brick wall, a mounted shark, and various bottles and glasses on shelves.

A hotel lobby with a high ceiling, large windows, and a blue and white color scheme. Tables and chairs are arranged for dining or meetings.

20. Graduate by Hilton Annapolis

Annapolis

CNY981

CNY1,119 total

includes taxes & fees

Oct 26 - Oct 27

See more properties

Top landmarks in Sherwood

Goat Island

Goat Island is 1.5 mi (2.4 km) from central Sherwood, why not stop by during your stay.

Back Creek Community Park

Back Creek Community Park is worth a visit, located 2.8 mi (4.5 km) from central Sherwood.