Vacation Rentals in Shelter Island Historical Society, NY: Compare 10+ Sites & Save

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  6.  Shelter Island Historical Society

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547 Best Vacation Rentals in Shelter Island Historical Society (Starting from $118)

West Neck Guesthouse
West Neck Guesthouse
House
Shelter Island Heights, NY, USA
2.4k from Shelter Island Historical Society center

Internet, View, Fireplace/Heating, Air Conditioner, Guest Services, Parking, Security/Safety

6 Bedrooms8 Guests
8.9

Fabulous

17 reviews

$358
Average price / night
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Shelter Island - spacious 4 bdrm home near beach! Heavenly, peaceful oasis
Shelter Island - spacious 4 bdrm home near beach! Heavenly, peaceful oasis
House
Shelter Island, NY, 11964, United States
0.2k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms6 Guests
New to Booking
$674
Average price / night
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Sandpoint by Rove Travel Modern 5BR Family Home with Pool
Sandpoint by Rove Travel Modern 5BR Family Home with Pool
House
Shelter Island, NY, USA
3.1k from Shelter Island Historical Society center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1760
Average price / night
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Charming, Renovated Island Cottage - Shelter Island License #:  012-2017
Charming, Renovated Island Cottage - Shelter Island License #: 012-2017
Cottage
Shelter Island, NY, 11964, United States
0.3k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

33 reviews

$371
Average price / night
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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
4.5k from Shelter Island Historical Society center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
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Updated Greek Revival home minutes to beaches and amenities
Updated Greek Revival home minutes to beaches and amenities
House
Shelter Island, NY, 11964, United States
0.7k from Shelter Island Historical Society center

AC, Dryer, Internet, Laundry, No Smoking, Pool, Washer

5 Bedrooms7 Guests
New to Booking
$744
Average price / night
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Modern on 9th
Modern on 9th
House
Greenport, NY, USA
5.0k from Shelter Island Historical Society center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$403
Average price / night
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Charming, Historic Cottage
Charming, Historic Cottage
Cottage
Shelter Island, NY, 11964, United States
0.8k from Shelter Island Historical Society center

AC, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$752
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
5.1k from Shelter Island Historical Society center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island Hts
Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island Hts
House
Shelter Island, NY, 11964, United States
0.8k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$844
Average price / night
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Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Apartment
Greenport, NY, USA
5.1k from Shelter Island Historical Society center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$208
Average price / night
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Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$972
Average price / night
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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
5.3k from Shelter Island Historical Society center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms10 Guests
New to Booking
$559
Average price / night
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Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

AC, Dryer, Free Parking, Heater, Kitchen, No Smoking, Patio, Pool, TV

3 Bedrooms6 Guests
New to Booking
$997
Average price / night
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Charming Greenport Gem 1, 1 Mile to Ferry!
Charming Greenport Gem 1, 1 Mile to Ferry!
Apartment
Greenport, NY, USA
5.3k from Shelter Island Historical Society center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$118
Average price / night
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Private wooded summer house 5 minute walk to Wades Beach
Private wooded summer house 5 minute walk to Wades Beach
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$773
Average price / night
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Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
6.1k from Shelter Island Historical Society center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
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Shelter Island Sun Filled Modern Waterfront Home with Dock
Shelter Island Sun Filled Modern Waterfront Home with Dock
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island Historical Society center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$411
Average price / night
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Lavender Bay Breezes - Private Bay Beach Community
Lavender Bay Breezes - Private Bay Beach Community
House
Shelter Island Historical Society, Shelter Island, New York, USA
6.1k from Shelter Island Historical Society center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay, Accessible hotels

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
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Shelter Island 4 bedroom waterfront home with home office
Shelter Island 4 bedroom waterfront home with home office
House
Shelter Island, NY, 11964, United States
1.0k from Shelter Island Historical Society center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms10 Guests
New to Booking
$1838
Average price / night
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SHELTER ISLAND YEARLY RENTAL - Perfect family home 4500 a month
SHELTER ISLAND YEARLY RENTAL - Perfect family home 4500 a month
House
Shelter Island, NY, 11964, United States
1.1k from Shelter Island Historical Society center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms4 Guests
New to Booking
$661
Average price / night
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Spacious 5-bedroom house in delightful Shelter Island
Spacious 5-bedroom house in delightful Shelter Island
House
Shelter Island, NY, 11964, United States
1.1k from Shelter Island Historical Society center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
New to Booking
$656
Average price / night
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
House
Shelter Island, NY, 11964, United States
1.2k from Shelter Island Historical Society center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

29 reviews

$471
Average price / night
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
House
Shelter Island, NY, 11964, United States
1.2k from Shelter Island Historical Society center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

39 reviews

$942
Average price / night
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 Contemporary Home with heated pool and waterviews on Shelter Island
Contemporary Home with heated pool and waterviews on Shelter Island
House
Shelter Island, NY, 11964, United States
1.2k from Shelter Island Historical Society center

AC, Barbecue, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, Pool

4 Bedrooms8 Guests
10.0

Exceptional

12 reviews

$1640
Average price / night
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4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres
House
Shelter Island, NY, 11964, United States
1.3k from Shelter Island Historical Society center

AC, Barbecue, Free Parking, Heater, Internet, Microwave, No Smoking, TV

4 Bedrooms14 Guests
New to Booking
$799
Average price / night
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Gorgeous Shelter Island Retreat with Pool and Private Grounds
Gorgeous Shelter Island Retreat with Pool and Private Grounds
House
Shelter Island, NY, 11964, United States
1.3k from Shelter Island Historical Society center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms8 Guests
New to Booking
$1057
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Shelter Island Historical Society.

Where to stay in Shelter Island Historical Society? Best neighborhoods & areas

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Frequently Asked Questions

You can explore 547 verified vacation rentals in Shelter Island Historical Society. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Shelter Island Historical Society vary depending on the season, property size, and location. Rates typically start from around $118 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Shelter Island Historical Society include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Shelter Island Historical Society welcome pets. Currently, 36 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Shelter Island Historical Society often include amenities such as Fireplace/Heating, Laundry, and Wellness Facilities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.