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

Winery Hotels & Resorts in Sherwood from AU$158

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Check availability on Sherwood Winery Hotels

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

Our top choices for Sherwood hotels with winery

A large, two-story barn-style building with a covered front porch and a garage.
A large, two-story white house with a porch and multiple windows.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

1. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
AU$273
includes taxes & fees
12 Oct - 13 Oct
Kent Island Resort
A modern living room with a large window, a dining area, and a kitchen in the background.
An outdoor patio with a brick floor, surrounded by lush greenery and trees.
A modern hotel lobby with grey sofas, wooden accents, and a large TV on the wall.
A modern gym with weight racks, benches, and exercise equipment.

2. Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
Annapolis
United States
Stacy
AU$158
includes taxes & fees
4 Oct - 5 Oct
Candlewood Suites Annapolis by IHG
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.
A marina with multiple boats docked, a grassy area, and a small building with a red roof.
A paved pathway with benches on either side, surrounded by lush greenery and trees.
A living room with a dark gray sofa, a small round table, and a green throw blanket. There is a brick accent wall and a ceiling fan.

3. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
United States
Kristen S.
AU$543
includes taxes & fees
29 Sept - 30 Sept
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Three birds perched on a wooden structure by the water.
A cozy living room with a ceiling fan, a dining area with chairs and a table, and large windows offering a view of the outdoors.
A beach with a thatched-roof hut, a white building with a red roof, and a wooden structure with a curved roof.

4. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
AU$1,830
includes taxes & fees
27 Sept - 28 Sept
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A house with a brick exterior, a front porch with a bench, and hanging flower baskets.
An outdoor patio with a table and chairs, a large umbrella, and a view of a garden and trees.
A two-story house with a covered porch, a brick facade, and a well-maintained lawn.
A bedroom with a bed, a ceiling fan, a window with curtains, and a dresser.

5. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
AU$605
includes taxes & fees
1 Oct - 2 Oct
The Harness Creek Retreat in Annapolis
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.
A two-story house with a large front porch and a covered patio area.
A kitchen with white cabinets, a central island with stools, a dining area with a table and chairs, and a view through the glass doors.
A dining area with a white table, a vase of flowers, and a staircase.

6. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
United States
David R.
AU$2,004
includes taxes & fees
27 Sept - 28 Sept
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A wooden dock extending into a calm body of water with boats docked at the end.
A modern living room with a white sofa, a coffee table, and a potted plant.
A two-story house with a porch, a flag, and a welcome sign.
A kitchen with wooden flooring, stainless steel appliances, a white door, and a white dining table with chairs.

7. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
United States
Nancy N.
AU$604
includes taxes & fees
5 Oct - 6 Oct
Cozy 2br home w/ parking in downtown Annapolis
A spacious living room with a large TV, blue sofa, and a ceiling fan.
A modern kitchen with stainless steel appliances, wooden countertops, and a dog lying on the floor.
A covered patio with wicker furniture and a wooden table, overlooking a grassy yard.
A room with large windows, two blue chairs, a white table, and a lamp.

8. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
United States
Ximena G.
AU$1,007
includes taxes & fees
5 Oct - 6 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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Top Sherwood Hotel Reviews

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