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Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Shelter Island

Property grounds
Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
United States
moshe A.
The price is ￥110,923
￥205,057 total
includes taxes & fees
Nov 14 - Nov 15
Work and Play Special! Extended Stay Discount
Front of property - evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1261)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
The price is ￥21,353
￥27,410 total
includes taxes & fees
Dec 3 - Dec 4
Montauk Manor
Beach nearby
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (248)
"Location good. Room could use some renos."
United States
Laura
Cliffside Resort Condominiums
Apartment | Private kitchen | Fridge, microwave, stovetop
Montauk Oceanside Suites

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (235)
"Great place for families and to enjoy the beauty of Montauk without being in Montauk town. Beautiful beach next to a state park so feels secluded and not crowded. Highly recommend!!!"
United States
Angel
Driftwood Resort
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is ￥11,696
￥28,465 total
includes taxes & fees
Nov 18 - Nov 19
1-bedroom cottage with Grove Beach 🏖️ access.
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu
Offshore Residences

Offshore Residences

4.5 star property
Downtown Montauk
The price is ￥73,795
￥101,912 total
includes taxes & fees
Nov 17 - Nov 18
Offshore Residences
Exterior
Shoreline Oasis

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is ￥27,577
￥40,456 total
includes taxes & fees
Nov 15 - Nov 16
Shoreline Oasis
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
9.8 out of 10, Exceptional, (74)
"This house was made for gatherings and has a massive cook's kitchen. Comfortable and tastefully decorated. A very lovely property."
United States
Linda C.
Stunning Hampton Holiday Family Fantasy for your Team
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Hampton Bays
9.6 out of 10, Exceptional, (142)
"Had a lovely time at our stay! Only regret was that we couldn’t stay longer, there were so many amenities we couldn’t take full advantage of. Such a beautiful property!"
United States
Gina K.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Outdoor pool, a heated pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays
9.4 out of 10, Exceptional, (75)
"As always everything was excellent, This is our third stay at this property and we are booked for 2026"
United States
Michael R.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Smart TV, fireplace, stereo
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Pool
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Southampton
9.0 out of 10, Wonderful, (10)
"Enjoyed our time. House was clean, pool was a bonus for the family after a day at the beach. House was spacious and welcoming. Beds were very comfortable.Location was perfect! Would definitely come back!"
United States
Panagiota K.
The price is ￥185,796
￥300,808 total
includes taxes & fees
Dec 1 - Dec 2
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"
United States
Edward
The price is ￥37,595
￥48,030 total
includes taxes & fees
Nov 16 - Nov 17
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Dining
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
9.8 out of 10, Exceptional, (34)
"This old colonial home was very charming. We enjoyed our stay. The only thing to be aware of is there is only air conditioning in 4 of the bedrooms and it was quite hot while we were there. The location is great, and it's a short walk in to town."
United States
LauraLee E.
Large Charming Historic House close to Beaches
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is ￥11,715
￥29,788 total
includes taxes & fees
Nov 19 - Nov 20
The Stern at Soundview · Beach+Ocean+Sunrise
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
Waterford
10.0 out of 10, Exceptional, (12)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is ￥22,046
￥48,096 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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.
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Top Shelter Island Hotel Reviews

Madison Beach Hotel

Madison Beach Hotel

10/10 Excellent
"Everything was perfect!!!!!"
Evelyn 2-night trip
Posted 2 days ago
Madison Beach Hotel

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday 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.

What are some of the best vacation home rentals that Shelter Island has to offer?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This vacation home rental near Shelter Island is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island?

Choose from 85 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.