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, (1023)
"Best affordable hotel in Montauk"
The price is RM 1,406
per night
6 Jun - 7 Jun
Montauk Manor
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (238)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is RM 1,136
per night
9 Jun - 10 Jun
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, (222)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is RM 1,170
per night
13 Jun - 14 Jun
The Surf Club
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Montauk Oceanside Suites
Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (302)
"This is our second time staying at Montauk Oceanside Suites and we enjoyed both times. It is very close to the beach and a short walk to dining options. We only used of car once(to dine on the bay side) over three days. We would defiantly stay there again."
The price is RM 763
per night
6 Jun - 7 Jun
Montauk Oceanside Suites
Driftwood Resort
Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (187)
"Such a nice weekend getaway. We probably rented the smallest of the rooms but it was still comfortable and accommodating. Had a mini kitchen that was perfect for us. ALL the staff were so friendly and helpful. I enjoyed the communications through text to set up room service and beach chairs for the next day. The heated pool was an absolute plus and so was the pool playing by the pool. Made us feel like we were away on an all inclusive vacation. "
The price is RM 931
per night
9 Jun - 10 Jun
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 RM 1,320
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
Property grounds
Pier Blue Inn Old Saybrook - Essex
2.0 star property
7.6 out of 10, Good, (789)
"Very clean room, nice view of the costal area from balcony. They are under remodling so some areas were umderstamdaly rough. Bit the awesome staff find us the perfect room was appreciated. We will stay there again soon."
The price is RM 371
per night
9 Jun - 10 Jun
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook
Indoor pool, pool loungers
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (967)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great. "
The price is RM 476
per night
19 Jun - 20 Jun
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 RM 2,729
per night
10 Jun - 11 Jun
Gurney's Montauk Resort & Seawater Spa
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.uk! 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
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • 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

Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

5/5 Excellent
"I love the location "
A verified traveller stayed at Beachcomber Resort at Montauk
Posted 1 day ago
Beachcomber Resort at Montauk