Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Shelter Island vacation rentals

A balcony with a view of the ocean, a lawn, and a house in the background.

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ￥30,352
￥52,208 total
includes taxes & fees
Nov 26 - Nov 27
Cliffside Resort Condominiums
A two-story house with a white staircase, a covered patio with outdoor furniture, and a fenced yard.

2. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (29 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is ￥13,510
￥36,377 total
includes taxes & fees
Nov 22 - Nov 23
Harbor Heights
A covered patio with outdoor furniture, a door, and a view of a residential area.

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (58 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is ￥15,011
￥38,272 total
includes taxes & fees
Nov 30 - Dec 1
The SandPiper
A metal compass sign with the words "AQUA VISTA GREENPORT" on a building's exterior wall.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (53 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥15,011
￥36,469 total
includes taxes & fees
Dec 1 - Dec 2
Aqua Vista
A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

5. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
United States
Callie E.
The price is ￥20,620
￥54,970 total
includes taxes & fees
Nov 16 - Nov 17
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A small, single-story house with a gabled roof, a front door, and a number "401" on the door.

6. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is ￥30,812
￥67,696 total
includes taxes & fees
Nov 16 - Nov 17
Beach Block Hideaway
A modern house with a deck, outdoor seating, and a fire pit.

7. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ￥48,738
￥55,683 total
includes taxes & fees
Nov 22 - Nov 23
North Fork Resort
A patio area with wicker chairs and a table, surrounded by gravel and plants.

8. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is ￥31,444
￥45,856 total
includes taxes & fees
Nov 16 - Nov 17
American Beech in Greenport - Petite King Room 7
A spacious hallway with high ceilings, arched columns, and chandeliers.

9. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,422 reviews)
"We’ve been to Montauk Manor many times. The inside pool area is updated and nice to use. Gavin a restaurant there is quite convenient. The units are comfortable and lovely with fully stocked kitchens."
United States
barbara
The price is ￥21,965
￥28,196 total
includes taxes & fees
Nov 30 - Dec 1
Montauk Manor
A modern dining area with a wooden table, white chairs, and a chandelier.

10. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (9 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is ￥44,929
￥95,874 total
includes taxes & fees
Nov 11 - Nov 12
Northfork Townhouse walk to all
Room

11. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
United States
Banessa
The price is ￥20,881
￥28,165 total
includes taxes & fees
Nov 11 - Nov 12
Windward Shores Ocean Resort
A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

12. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is ￥35,515
￥83,671 total
includes taxes & fees
Nov 11 - Nov 12
Renovated Townhouse walk to all
A kitchen with a wooden countertop, a black sink, and a window with a view of trees.

13. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.

North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
United States
Kelly V.
The price is ￥39,620
￥74,961 total
includes taxes & fees
Nov 11 - Nov 12
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
A modern living room with a sofa, coffee table, and dining area.

14. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is ￥76,635
￥134,313 total
includes taxes & fees
Dec 1 - Dec 2
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A small cabin with a porch, surrounded by trees and a fenced area.

15. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥35,552
￥74,737 total
includes taxes & fees
Nov 18 - Nov 19
Lovely studio with AC in charming Sag Harbor
A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

16. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is ￥36,292
￥51,969 total
includes taxes & fees
Nov 11 - Nov 12
American Beech in Greenport - Deluxe King 6
A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

17. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥84,866
￥146,209 total
includes taxes & fees
Dec 9 - Dec 10
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

18. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
Year round Jacuzzi - Blackberry East Hampton Home
Room

19. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (461 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is ￥21,502
￥26,283 total
includes taxes & fees
Nov 24 - Nov 25
Montauk Oceanside Suites
A house with a sliding glass door, a white door, and a small porch with potted plants.

20. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ￥87,223
￥176,737 total
includes taxes & fees
Nov 12 - Nov 13
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
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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Find vacation rentals that suit your style

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Top Shelter Island Hotel Reviews

A beachside outdoor seating area with white Adirondack chairs and a fire pit.
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport

10/10 Excellent

We had a lovely stay.
United States
Nicole
Reviewed June 22, 2024
Silver Sands Motel & Beach Bungalows

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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island?

Choose from 87 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Mashomack Preserve and Sunset Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Wades Beach 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.

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