Holiday rentals in Shelter Island

Search among 52 available holiday rentals in Shelter Island from 50+ providers

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1-20 out of 52
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Shelter Island Retreat With Outdoor Pool! Villa
Villa
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Shelter Island Hidden Waterfront Villa
Villa
Map
1.1 km from City Centre
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Places to stay near Shelter Island
The Cliffside Resort Condominiums
Apartment
8.4
Great17 reviews
The largest option:
6 adults
2 bedrooms
3 beds
Map
5.6 km from Shelter Island5.6 km from City Centre
Guests will enjoy a seasonal outdoor swimming pool onsite and admire views of the sea offered from 65 rooms.
FromC$ 332 /nightSelect
Beautiful Sag Harbor Cottage Steps From The Water
Villa
Map
8.6 km from Shelter Island8.6 km from City Centre
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Beachside Waterview 2Br Condo W/ Pool In Greenport
Apartment
Map
5.6 km from Shelter Island5.6 km from City Centre
Rooms of the Beachside Waterview 2Br Condo W/ Pool In Greenport face the sea and there is also a seasonal outdoor swimming pool on the premises.
FromC$ 889 /nightSelect
Wonderful 6 Bedroom Home At Hamptons
Villa
Map
11.0 km from Shelter Island11.0 km from City Centre
FromC$ 1 211 /nightSelect
Charming Greenport Gem 1, 1 Mile To Ferry!
Apartment
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4.6 km from Shelter Island4.6 km from City Centre
Sylvester Manor Educational Farm is also set 4.2 km from the Charming Greenport Gem 1, 1 Mile To Ferry!.
FromC$ 389 /nightSelect
The Great Escape - Hamptons Serene Family Favorite
Villa
Map
14.1 km from Shelter Island14.1 km from City Centre
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Modern On 9Th
Villa
Map
4.2 km from Shelter Island4.2 km from City Centre
The Modern On 9Th Villa Greenport is merely 450 metres from Congregation Tifereth Israel and has a quick access to Fireboat Firefighter Museum.
FromC$ 256 /nightSelect
Sag Harbor Hideaway
Villa
Map
9.5 km from Shelter Island9.5 km from City Centre
There are rooms facing garden and the Hideaway Villa Sag Harbor is set approximately a 5-minute walk from Haven's Beach.
FromC$ 613 /nightSelect
Villa Direen
Villa
Map
15.0 km from Shelter Island15.0 km from City Centre
Guests of the quality Villa Direen East Hampton can relax at a private swimming pool and have their drinks at the pool bar.
FromC$ 1 201 /nightSelect
Cowgirl Palace
Homestay
Map
11.1 km from Shelter Island11.1 km from City Centre
FromC$ 544 /nightSelect
Classic Southold Country Charmer
Villa
Map
7.5 km from Shelter Island7.5 km from City Centre
While staying at the Classic Southold Country Charmer Villa Southold you are invited to discover Catapano Dairy Farm, set approximately 10 minutes' drive away, or Founders Landing Park, which is nearly 20 minutes' walk away.
FromC$ 150 /nightSelect
North Fork Waterfront Gem
Villa
Map
8.0 km from Shelter Island8.0 km from City Centre
Greenport is 4.5 km from this villa that offers 2 bedrooms along with an equipped kitchen.
FromC$ 723 /nightSelect
Villa Guldan - Luxury With Pool
Villa
14 adults
7 bedrooms
7 beds
Map
10.7 km from Shelter Island10.7 km from City Centre
Situated 2.6 km from Custom House Museum, this property features a flat screen TV, a bar and a garden.
FromC$ 17 800 /nightSelect
Villa Kimaal - Luxury With Pool
Villa
8 adults
5 bedrooms
5 beds
Map
9.5 km from Shelter Island9.5 km from City Centre
There are rooms facing garden and the Villa Kimaal - Luxury With Pool Sag Harbor is set approximately a 5-minute walk from Mashashimuet Park.
FromC$ 2 931 /nightSelect
Villa Ebrar - Luxury With Pool
Villa
3 adults
4 bedrooms
4 beds
Map
8.6 km from Shelter Island8.6 km from City Centre
Set within walking distance of Trout Pond Park, this villa includes 4 bedrooms and a kitchen for guests' convenience.
FromC$ 734 /nightSelect
Villa Zainip - Luxury With Pool
Villa
8 adults
5 bedrooms
5 beds
Map
11.1 km from Shelter Island11.1 km from City Centre
Rooms of the Villa Zainip - Luxury With Pool face the garden and there is also a private swimming pool on the premises.
FromC$ 5 445 /nightSelect
Lavender Bay Breezes - Private Bay Beach Community
Villa
8 adults
4 bedrooms
4 beds
Map
5.5 km from Shelter Island5.5 km from City Centre
The holiday home is equipped with an equipped kitchenette area along with 4 bedrooms and is set next to Lavender By the Bay.
FromC$ 446 /nightSelect
Villa Gally
Villa
8 adults
4 bedrooms
4 beds
Map
10.8 km from Shelter Island10.8 km from City Centre
Rooms of the Villa Gally East Hampton face the pool and there is also a private pool on the premises.
FromC$ 6 670 /nightSelect

Holiday rentals in Shelter Island essential information

🏨 Holiday rentals in Shelter Island 52
👛 Lowest price 150 CAD
✍️ Holiday rentals Reviews 17