Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Montauk Manor
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1022)
"Best affordable hotel in Montauk"
The price is ₩228,178
₩286,961 total
includes taxes & fees
May 30 - May 31
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (236)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is ₩283,348
₩352,875 total
includes taxes & fees
May 30 - May 31
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand
The Surf Club
3.5 star property
8.4 out of 10, Very Good, (220)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is ₩252,965
₩362,476 total
includes taxes & fees
May 30 - May 31
The Surf Club
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Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very Good, (299)
"Great place to stay"
The price is ₩229,658
₩275,674 total
includes taxes & fees
Jun 12 - Jun 13
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Well maintained upscale resort. "
The price is ₩218,141
₩278,459 total
includes taxes & fees
May 30 - May 31
Driftwood Resort
Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (183)
"Wonderful stay and super clean! Can’t wait to come back. "
The price is ₩370,612
₩481,971 total
includes taxes & fees
Jun 23 - Jun 24
Cliffside Resort Condominiums
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See all available properties in Shelter Island
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.

Other types of properties in Shelter Island you may be interested in

Quality Inn Old Saybrook - Westbrook
Indoor pool, sun loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (965)
"None"
The price is ₩137,382
₩157,990 total
includes taxes & fees
Jun 5 - Jun 6
Quality Inn Old Saybrook - Westbrook
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very Good, (570)
"Great time beautiful property"
The price is ₩715,092
₩974,912 total
includes taxes & fees
May 30 - May 31
Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
Terrace/patio
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (75)
"Spacious and clean with wonderful staff. "
The price is ₩243,824
₩336,219 total
includes taxes & fees
Jun 4 - Jun 5
The Bentley Hotel Southampton
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.

Search for Vacation rentals in Shelter Island on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Shelter Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shelter Island!

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

How many vacation rentals are there in Shelter Island?

Choose from 89 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

Recent reviews of Shelter Island properties
Expedia verified reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

5/5 Excellent
"It was a gem finding this property during our last minute memorial wknd . Booking . Expected goes above and beyond.luxury Property, amazing staff’s great restaurants & bars with amenities, friendly guests , we've met some guest also from NY extended stay due to fog issue in marina instead we enjoyed bonding at Cho Cho lounge on their Monday trivia . Jeff in that bar does a fantastic drinks ! Fresh Seafood meals we enjoyed as well facing marina . "
A verified traveler from Bayside stayed at Saybrook Point Resort & Marina
Posted 16 hours ago
Saybrook Point Resort & Marina