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Vacation rentals in Shelter Island

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Top vacation rentals in Shelter Island

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

1.32 mi from city center
$1,165 nightly
The price is $1,331 total per night
$1,331 total
Nov 5 - Nov 6
Total with taxes and fees
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Pool
Kitchen
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
20.31 mi from city center
$168 nightly
The price is $192 total per night
$192 total
Nov 10 - Nov 11
Total with taxes and fees
3 outdoor tennis courts, an indoor pool, and a 24-hour gym are all featured at this smoke-free aparthotel. Enjoy the seasonal outdoor pool and perks like free WiFi. There's a restaurant and a bar/lounge for dining and drinks, and also a hot tub on site.
Pool
Hot Tub
Montauk Oceanside Suites

Montauk Oceanside Suites

3 out of 5
115 South Emerson Avenue, Montauk, NY
20.69 mi from city center
$146 nightly
The price is $166 total per night
$166 total
Nov 5 - Nov 6
Total with taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Kitchen
Parking included
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
3.44 mi from city center
$262 nightly
The price is $299 total per night
$299 total
Nov 5 - Nov 6
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a picnic area, and barbecue grills are also on offer.
Pool
Kitchen
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
16.25 mi from city center
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This aparthotel's 2 outdoor tennis courts and seasonal outdoor pool are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and laundry facilities are also on offer.
Pool
Kitchen
Driftwood Resort

Driftwood Resort

3.5 out of 5
2178 Montauk Highway, Montauk, NY
16.79 mi from city center
$188 nightly
The price is $215 total per night
$215 total
Oct 23 - Oct 24
Total with taxes and fees
A private beach and a gym are featured at this condo. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A terrace, a garden, and express check-in are also on offer.
Pool
Kitchen
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

17.92 mi from city center
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A gym is featured at this cottage, along with a garden and barbecue grills.
Pool
Kitchen
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue, Montauk, NY
20.93 mi from city center
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This aparthotel features an outdoor pool and a gym. Enjoy the sauna and perks like free WiFi. Self parking, a terrace, and a picnic area are also offered.
Pool
Kitchen
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 out of 5
7.89 mi from city center
$328 nightly
The price is $374 total per night
$374 total
Oct 28 - Oct 29
Total with taxes and fees
This vacation home features an outdoor pool and a hot tub. A garden and barbecue grills are also provided.
Pool
Hot Tub
MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK MANOR-DELUXE STUDIO APARTMENT

20.16 mi from city center
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This apartment features an outdoor pool and an indoor pool. There's a gym on site, and laundry facilities and concierge services are also offered.
Pool
Kitchen
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

16.2 mi from city center
$155 nightly
The price is $176 total per night
$176 total
Nov 4 - Nov 5
Total with taxes and fees
This cottage features barbecue grills.
Kitchen
Air conditioning
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

18.37 mi from city center
$346 nightly
The price is $393 total per night
$393 total
Oct 29 - Oct 30
Total with taxes and fees
This apartment features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

15.06 mi from city center
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This vacation home featured laundry facilities and barbecue grills.
Kitchen
Washer
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

17.22 mi from city center
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This vacation home includes a garden and laundry facilities.
Kitchen
Washer
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

15.16 mi from city center
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.
Hot Tub
Kitchen
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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.

The Best Way to Find your Vacation Rentals in Shelter Island

How cheap can a vacation rental in Shelter Island be?

You can find vacation rentals in Shelter Island for as low as $166 per night.

How do you look for the best vacation rental deals in Shelter Island with Travelocity?

Travelocity provides the best vacation rental deals in various locations throughout Shelter Island so you can create the perfect plan for you. You can search and filter by type of property, amenities, neighborhood, price range, number of bedrooms, and more.

Are cancellations free on vacation rentals with Travelocity?

Each vacation rental has its own cancellation policy. It’s essential to understand the terms of your agreement before booking. Most rentals in Shelter Island can be canceled for free when notifying the property before the cancellation deadline.

What types of vacation rentals are available in Shelter Island?

Short term rentals come in all shapes and sizes. Choose from properties for a wide range of budgets and types of holidays. Families, couples, outdoor adventurers, and leisure travelers alike will find the perfect place for them. Check out our Shelter Island vacation apartments to get started building your trip.

What are the benefits of booking a short-term rental in Shelter Island?

Whether it’s for a summer getaway, a winter excursion, or a routine business trip, Shelter Island vacation homes are often an excellent choice. You can enjoy group vacations with short term rentals to fit your party size. You might take a romantic weekend for two or plan a family reunion, and all stay under one roof. The options are endless, and you can find them on Travelocity.

Why is Travelocity the best site to find your vacation rental in Shelter Island?

With Travelocity, all your travel needs are taken care of in one convenient platform. We offer fantastic deals on our large selection of vacation rentals to get you the most savings and rewards back on every booking. Save more when you bundle bookings together, including car rentals, flights, and activities. Here, you can build custom Shelter Island vacations.

How to cancel your vacation rental with Travelocity?

To cancel your vacation rental, contact the property manager. You can find their contact information in the ‘Itinerary’ section of your Travelocity account. Most properties receive a full refund when you cancel before the cancellation deadline. Policies vary by property, so it’s important to understand the terms before booking. For more information, visit our customer service portal.