A wooden gazebo by a pond with a large tree trunk nearby.

Winery Hotels & Resorts in Shelter Island from AU$278

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Check availability on Shelter Island 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 Shelter Island hotels with winery

A bedroom with a bed, bench, and windows with shutters.
A spacious living room with a fireplace, a sofa, and a coffee table.
A large two-story house with a swimming pool, multiple decks, and a well-maintained garden.

1. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach
Menantic Creek
United States
Harry K.
AU$1,660
includes taxes & fees
5 Oct - 6 Oct
Huge Island Getaway Pool Hot Tub Walk To Beach
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A grassy area with trees and a view of a body of water.

2. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
AU$459
includes taxes & fees
21 Oct - 22 Oct
Silver Sands Motel & Beach Bungalows
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.
A marina with several fishing boats docked.
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.
A wicker lounge chair with a white cushion on a covered deck, surrounded by a white fence.

3. Aqua Vista

Aqua Vista
Pipes Cove
United States
Kerri L.
AU$448
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.
A room with a sliding glass door leading to a garden, a small table, a chair, a television mounted on the wall, and a cabinet.
A two-story house with a front porch and a pathway leading to the entrance.
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

4. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
United States
Callie E.
AU$586
includes taxes & fees
28 Sept - 29 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.
A compact kitchen with white cabinets, a built-in oven, a microwave, and a washing machine.
A covered patio with outdoor furniture, a door, and a view of a residential area.
A sign welcoming visitors to the Greenport Visitors Dock with no commercial traffic.

5. The SandPiper

The SandPiper
Pipes Cove
United States
Julian V.
AU$459
includes taxes & fees
18 Oct - 19 Oct
The SandPiper
A waterfront property with a large house, multiple boats docked, and lush greenery.
A hotel lobby with a sofa, chairs, tables, and a large window.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
AU$520
includes taxes & fees
5 Oct - 6 Oct
Sag Harbor Inn
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

7. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
AU$747
includes taxes & fees
5 Oct - 6 Oct
Faraway Sag Harbor
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

8. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
AU$278
includes taxes & fees
30 Sept - 1 Oct
The Bentley Hotel Southampton
A modern living room with a sofa, coffee table, and dining area.
A dining area with a wooden table set for four, a kitchen in the background, and a view of a deck and garden through large windows.
A modern kitchen with white cabinets, a central island, and a TV on a wooden stand.
A modern kitchen with a stainless steel refrigerator, a dining area with a white table and chairs, and a large window with a view of greenery.

9. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
United States
Jeannette M.
AU$1,291
includes taxes & fees
6 Oct - 7 Oct
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.
A bedroom with a large bed, a ceiling fan, and a view of the ocean through large windows.
A wooden staircase leading to a house with two surfboards leaning against a wooden fence.
A sunlit room with large windows overlooking a beach, featuring a wooden table and chairs, and a small round table with a chair.

10. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
United States
Kate R.
AU$1,664
includes taxes & fees
20 Oct - 21 Oct
Beachfront Greenport Villa
View all properties

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"The staff at the Bistro Bar weren't very good. Also the drinks sub par. I ordered a gin and tonic, they served me soda water twice."
Linda 3-night trip
Posted 18 hours ago
Water's Edge Resort & Spa

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