Photo by tom owens

Shelter Island Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Shelter Island

Montauk Beach House Oasis — this Hither Hills Hideaway Has ALL the Stuff

10.0 out of 10, Exceptional, (1)
"The house is very efficient and well stocked. Everything was clean and tidy and Ric was very responsive and accommodating. The house comes with access to an HOAA beach which was a great bonus. We were four adults and were very comfortable in the house. Kitchen is well stocked for making meals at home. Looking forward to visiting again!"
The price is AU$1,490
includes taxes & fees
15 July - 16 July
Montauk Beach House Oasis — this Hither Hills Hideaway Has ALL the Stuff

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is AU$2,082
includes taxes & fees
10 July - 11 July
Cozy quiet gem, private & fenced in backyard

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

10.0 out of 10, Exceptional, (7)
"Open concept home beautiful with private yard space. It was perfect for our stay"
The price is AU$887
includes taxes & fees
15 July - 16 July
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

East Hampton slice of heaven with heated pool and 3 minute drive to village.

9.6 out of 10, Exceptional, (18)
"We loved the simple « ranch » layout with an architectural twist and the beautiful swimming pool And we really appreciated all the little attentions and touches that made our stay feel like a real vacation! Thank you Dorothy!"
The price is AU$3,287
includes taxes & fees
4 Aug - 5 Aug
East Hampton slice of heaven with heated pool and 3 minute drive to village.

Stylish Modern Retreat in the Heart of the Hamptons: Your Perfect Getaway!

10.0 out of 10, Exceptional, (8)
"Great location and amenities. "
The price is AU$5,871
includes taxes & fees
22 July - 23 July
Stylish Modern Retreat in the Heart of the Hamptons: Your Perfect Getaway!

east hampton getaway

The price is AU$2,929
includes taxes & fees
2 Aug - 3 Aug
east hampton getaway

Cheerful 3bd Cape yards from beach/ river access

10.0 out of 10, Exceptional, (5)
"Nicely decorated house. Close to Mystic, Mohegan Sun and multiple beaches and state parks. My son loved the house as well. Very accommodating and had a lot of things that were helpful (beach chairs, bikes, blankets, shades/curtains, suggestions on where to eat). Overall a great place to stay!"
The price is AU$1,425
includes taxes & fees
24 July - 25 July
Cheerful 3bd Cape yards from beach/ river access

2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

10.0 out of 10, Exceptional, (33)
"We stayed at this wonderful property for 3 nights and it had everything we were looking and more! Looking forward to our next visit!"
The price is AU$928
includes taxes & fees
20 July - 21 July
2BED GUESTHOUSE WITH PRIVATE BEACH ACCESS

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.8 out of 10, Exceptional, (8)
"Great place! Great communication with property owner!"
The price is AU$980
includes taxes & fees
7 July - 8 July
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Sag Harbor Water View w Dock

The price is AU$10,216
includes taxes & fees
17 July - 18 July
Sag Harbor Water View w Dock

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is AU$9,913
includes taxes & fees
11 July - 12 July
Spacious 5-bedroom house with water views and 2 houses from the bay.

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!"
The price is AU$641
includes taxes & fees
9 July - 10 July
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

10.0 out of 10, Exceptional, (1)
"Great location to see all the eastern LI towns. The house is well appointed and nicely decorated. Easy communication with the host. "
The price is AU$1,908
includes taxes & fees
20 July - 21 July
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

Stunning Southampton Village Modern Home

The price is AU$25,404
includes taxes & fees
7 July - 8 July
Stunning Southampton Village Modern Home

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

9.2 out of 10, Wonderful, (9)
"Great location and comfortable home. Easy check in and check out."
The price is AU$2,093
includes taxes & fees
7 July - 8 July
Entire House in Southampton Village, Pool, 2 Fireplaces, Walk Everywhere, Pets!

Village gem walk to Main Street fenced in property

8.8 out of 10, Excellent, (3)
"Second year at this lovely house for the 4th of July extended weekend. The hosts are responsive and helpful, and the house is exactly what you need for 2-3 people. Very clean, nicely decorated, kitchen was nicely stocked. It is in a great location. Easily able to walk into town for shopping or dining."
The price is AU$2,001
includes taxes & fees
13 July - 14 July
Village gem walk to Main Street fenced in property

Contemporary w Spacious Open Design for dates in August/LDW

2.0 star property
The price is AU$3,879
includes taxes & fees
3 Aug - 4 Aug
Contemporary w Spacious Open Design for dates in August/LDW

Charming Village home in the heart of Southampton

10.0 out of 10, Exceptional, (22)
"Great location, clean, easy checkin, slept 7 comfortably"
The price is AU$2,950
includes taxes & fees
7 July - 8 July
Charming Village home in the heart of Southampton

Minutes from the beach, brand new 4 bedroom

The price is AU$2,255
includes taxes & fees
7 July - 8 July
Minutes from the beach, brand new 4 bedroom

American Beech in Greenport NY - King Suite 1

10.0 out of 10, Exceptional, (5)
"Perfect Great place"
The price is AU$673
includes taxes & fees
22 July - 23 July
American Beech in Greenport NY - King Suite 1
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

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

Escape to Sag Harbor: This holiday home rental outside of Shelter Island offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a pool table so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island?

Choose from 87 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. Gardiner's Bay Country Club and Mashomack Preserve 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.