Winery Hotels & Resorts in Shelter Island from AU$155

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Our top choices for Shelter Island hotels with winery

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (128)
"Great location. Nice and clean room and property"
United States
Eric
The price is AU$155
includes taxes & fees
23 Dec - 24 Dec
The Niantic Inn

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (401)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AU$218
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is AU$570
includes taxes & fees
22 Dec - 23 Dec
Mill House Inn

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (91)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is AU$1,078
includes taxes & fees
1 Jan - 2 Jan 2026
The Roundtree, Amagansett

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (576)
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is AU$372
includes taxes & fees
22 Dec - 23 Dec
Sag Harbor Inn

Shoreline Oasis

Shoreline Oasis
Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is AU$398
includes taxes & fees
22 Dec - 23 Dec
Shoreline Oasis

Blackberry: Private home with jacuzzi year-round

Blackberry: Private home with jacuzzi year-round
East Hampton
9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is AU$1,396
includes taxes & fees
4 Jan - 5 Jan 2026
Blackberry: Private home with jacuzzi year-round

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
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is AU$889
includes taxes & fees
7 Jan - 8 Jan 2026
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Wainscott
10.0 out of 10, Exceptional, (112)
"We had a great stay at the house - it's perfect for a family and the kids love the pool ! Would definitely stay again and perfect for long term rental as well."
United States
Amy P.
The price is AU$2,422
includes taxes & fees
30 Dec - 31 Dec
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Shelter Island Hotel Reviews

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