Compare Shelter Island Vacation Rentals

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Shelter Island Rentals

Waterfront House With Dock And Private Beach

Waterfront House With Dock And Private Beach

1.52 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
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

0.77 mi from city center
At this vacation home, guests have access to barbecue grills.
Pet friendly
Air conditioning
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
3.44 mi from city center
$326 nightly
The price is $372 total per night
$372 total
Oct 26 - Oct 27
Total with taxes and fees
At Cliffside Resort Condominiums, guests have access to free WiFi in public areas, a seasonal outdoor pool, and a terrace. If you plan to drive, free parking is available. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach aparthotel include laundry facilities, a picnic area, and a vending machine.
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
$356 nightly
The price is $406 total per night
$406 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at this vacation home enjoy an outdoor pool, a hot tub, and barbecue grills. Additional amenities include a garden and a water dispenser.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

11.69 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly vacation home include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Hot Tub
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
$151 nightly
The price is $172 total per night
$172 total
Oct 19 - Oct 20
Total with taxes and fees
Guests of Windward Shores Ocean Resort enjoy outdoor tennis courts, free WiFi in public areas, and a seasonal outdoor pool. Free parking is included with your stay. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing. Other amenities at this beach aparthotel include free newspapers, a terrace, and laundry facilities.
Pool
Kitchen
Driftwood Resort

Driftwood Resort

3.5 out of 5
2178 Montauk Highway, Montauk, NY
16.79 mi from city center
$174 nightly
The price is $199 total per night
$199 total
Oct 31 - Nov 1
Total with taxes and fees
Guests staying at Driftwood Resort enjoy access to a private beach, a gym, and free WiFi in public areas. You can put free parking to good use if you drive. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Other amenities at this beach condo building include a seasonal outdoor pool, an arcade/game room, and express check-in.
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
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Pool
Kitchen
Shoreline Oasis

Shoreline Oasis

17.51 mi from city center
$232 nightly
The price is $263 total per night
$263 total
Oct 5 - Oct 6
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
20.31 mi from city center
$146 nightly
The price is $167 total per night
$167 total
Oct 27 - Oct 28
Total with taxes and fees
Guests staying at Montauk Manor enjoy an indoor pool, a 24-hour gym, and a sauna. Transportation is made easy with an area shuttle. The 24-hour front desk has staff standing by to help with luggage storage, securing valuables, and concierge services. Additional amenities include outdoor tennis courts, free WiFi in public areas, and a hot tub.
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
Oct 20 - Oct 21
Total with taxes and fees
Montauk Oceanside Suites features free WiFi in public areas and a picnic area. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide front-desk service during limited hours. This aparthotel also has barbecue grills.
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue, Montauk, NY
20.93 mi from city center
$318 nightly
The price is $363 total per night
$363 total
Oct 13 - Oct 14
Total with taxes and fees
Guests of The Surf Club have access to an outdoor pool, a gym, and a sauna. Onsite parking is offered for a fee. Front-desk staff can assist with luggage storage and concierge services. Other amenities at this beach aparthotel include free WiFi in public areas, a terrace, and laundry facilities.
Pool
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.

Shelter Island Large Group Rentals

How to Book Vacation Rentals in Shelter Island



🏠 What is the best price for Shelter Island vacation rentals?

Shelter Island vacation rentals range in price, starting at $166 per night.


🏠 What types of vacation rentals in Shelter Island can I rent?

Orbitz offers a wide range of Shelter Island rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Shelter Island condo rentals.


🏠 Is it free to cancel my Shelter Island vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Shelter Island vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Shelter Island. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Shelter Island?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Shelter Island apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Shelter Island?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Shelter Island package deals will get you even more savings.

More to Explore

More to Explore