Compare Shelter Island Vacation Rentals

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Shelter Island Rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
3.44 mi from city center
The price is $242 per night
$242
includes taxes & fees
$212 per night
May 7 - May 8
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.
Location and views! Located directly on Shinnecock Bay!

Location and views! Located directly on Shinnecock Bay!

14.1 mi from city center
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
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
The price is $197 per night
$197
includes taxes & fees
$173 per night
May 6 - May 7
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
The price is $191 per night
$191
includes taxes & fees
$167 per night
May 6 - May 7
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
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

19.54 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this beach vacation home include barbecue grills and a garden.
Pool
Hot Tub
Newly Renovated Montauk Condo with Ocean Views!

Newly Renovated Montauk Condo with Ocean Views!

19.83 mi from city center
At this apartment, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free apartment building also has a garden.
Pool
Kitchen
Montauk Mansion INDOOR + OUTDOOR POOLS

Montauk Mansion INDOOR + OUTDOOR POOLS

20.16 mi from city center
This condo features an indoor pool, an outdoor pool, and a gym. Additional amenities include a sauna, a hot tub, and laundry facilities.
Pool
Hot Tub
MONTAUK MANOR-DELUXE STUDIO APARTMENT

MONTAUK MANOR-DELUXE STUDIO APARTMENT

20.16 mi from city center
This apartment features an indoor pool, an outdoor pool, and a gym. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include a sauna, laundry facilities, and a garden.
Pool
Kitchen
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
20.31 mi from city center
The price is $208 per night
$208
includes taxes & fees
$182 per night
May 6 - May 7
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 concierge services, luggage storage, and securing valuables. Additional amenities include outdoor tennis courts, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

20.32 mi from city center
The price is $620 per night
$620
includes taxes & fees
$543 per night
May 26 - May 27
This condo features an indoor pool, an outdoor pool, and a gym. Additional amenities include a sauna, a hot tub, and laundry facilities.
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
The price is $192 per night
$192
includes taxes & fees
$168 per night
May 6 - May 7
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.
Kitchen
Parking included
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue, Montauk, NY
20.93 mi from city center
The price is $286 per night
$286
includes taxes & fees
$250 per night
May 19 - May 20
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.
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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 $191 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.

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