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Search Holiday Rentals in Shelter Island

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Top Holiday Rentals in Shelter Island

Montauk Manor
Exterior
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1030)
"Was visiting family who still live in Montauk. I grew up in Montauk as a kid until i married so very familiar with the area. Loved it then but now its just too, too busy and so many homes and shops, & people. Lots of memories came back even those of watching a movie in the old movie theater & holding an umbrella up over us if it was raining and the cats wandering around brushing up against our legs! Or were they rats??? Lol. The Manor was great though, beautiful and all was perfect! Your...
The price is Rp7.442.438
per night
27 Jun - 28 Jun
Montauk Manor
The Surf Club
Exterior
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (227)
"Very nice location and nice condo"
The price is Rp7.143.594
per night
30 Jun - 1 Jul
The Surf Club
Driftwood Resort
Property grounds
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (192)
"Staff is friendly "
The price is Rp5.076.414
per night
27 Jun - 28 Jun
Driftwood Resort
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Montauk Oceanside Suites
Front of property
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (307)
"Amazing stay! Would highly recommend. "
The price is Rp5.570.775
per night
21 Jul - 22 Jul
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (241)
"Access to the beach. "
The price is Rp7.371.698
per night
7 Jul - 8 Jul
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Pool Side, First Floor | 2 bedrooms, iron/ironing board, free WiFi
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (185)
"Had issue with check in. Nothing sent to phone as stated because of limited cell service in area. Had to go to office to get room and code. They have wrong room and had to go back for correct room. This was frustrating because it was after the check in time, which is later than most properties. The unit was fine, bare bones with decor etc. shower in one bathroom was leaking. I have stayed on property few times. This time was definitely less impressive."
The price is Rp5.107.035
per night
27 Jun - 28 Jun
Cliffside Resort Condominiums
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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.

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

Pier Blue Inn Old Saybrook - Essex
Exterior
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.8 out of 10, Good, (804)
"Very nice hotel and service "
The price is Rp1.293.625
per night
30 Jun - 1 Jul
Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton
2.0 star property
9.4 out of 10, Exceptional, (98)
"The property was well thought out, a great space to relax for a weekend in the Hamptons. Friendly staff, clean, and close to town. Our room had 2 air conditioners so it was nice and cool, plenty of space for 2 people"
The price is Rp3.890.700
per night
15 Jul - 16 Jul
The Bentley Hotel Southampton
Sound View Greenport
Private beach, sun-loungers, beach umbrellas, beach towels
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (440)
"We didn't have a table and chairs outside. We called the front desk and asked for them. They never came. We got our beach chairs out of our car to use."
The price is Rp7.307.344
per night
8 Jul - 9 Jul
Sound View Greenport
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 holiday rentals in Shelter Island on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island
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  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

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

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals are there in Shelter Island?

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

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. Shell Beach and Gardiner's Bay Country Club are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.

Recent reviews of Shelter Island properties
Expedia verified reviews

The Montauk Soundview

The Montauk Soundview

5/5 Excellent
"The room was the perfect size and had a nice balcony. It was clean - loved the pool and overall had a great vibe "
A verified traveller stayed at The Montauk Soundview
Posted 2 days ago
The Montauk Soundview