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Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Shelter Island vacation rentals

A modern house with a deck, outdoor seating, and a fire pit.

1. 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 AED 1,180
AED 1,348 total
includes taxes & fees
8 Nov - 9 Nov
North Fork Resort
A balcony with a view of the ocean, a lawn, and a house in the background.

2. 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 AED 632
AED 1,129 total
includes taxes & fees
30 Nov - 1 Dec
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

3. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is AED 314
AED 846 total
includes taxes & fees
8 Nov - 9 Nov
Harbor Heights
A beach with people relaxing, a pier extending into the water, and a clear sky.

4. 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 AED 479
AED 1,244 total
includes taxes & fees
8 Nov - 9 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A sign on a porch with the text "The Sandpiper" and "Greenport, NY".

5. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (57 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 AED 314
AED 846 total
includes taxes & fees
10 Nov - 11 Nov
The SandPiper
A wooden pathway leading to a beach with scattered rocks and greenery.

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 AED 716
AED 1,574 total
includes taxes & fees
11 Nov - 12 Nov
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

7. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AED 349
AED 890 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
An outdoor dining area with hanging lights, palm trees, and a bar.

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 AED 731
AED 1,066 total
includes taxes & fees
8 Nov - 9 Nov
American Beech in Greenport - Petite King Room 7
A modern living room with a sofa, coffee table, and dining area.

9. 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 AED 1,715
AED 3,038 total
includes taxes & fees
18 Nov - 19 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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 AED 1,107
AED 2,247 total
includes taxes & fees
19 Nov - 20 Nov
Northfork Townhouse walk to all
A wooden deck with two Adirondack chairs and a fire pit, overlooking a beach at sunset.

11. 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 AED 2,264
AED 3,800 total
includes taxes & fees
6 Dec - 7 Dec
Beachfront Greenport Villa
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 AED 859
AED 1,935 total
includes taxes & fees
11 Nov - 12 Nov
Renovated Townhouse walk to all
A spacious hallway with high ceilings, arched columns, and chandeliers.

13. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,420 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is AED 509
AED 654 total
includes taxes & fees
30 Nov - 1 Dec
Montauk Manor
A house with a sliding glass door, a white door, and a small porch with potted plants.

14. 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.
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

15. 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 AED 841
AED 1,204 total
includes taxes & fees
19 Nov - 20 Nov
American Beech in Greenport - Deluxe King 6
Room

16. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (332 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 AED 484
AED 653 total
includes taxes & fees
8 Nov - 9 Nov
Windward Shores Ocean Resort
A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

17. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is AED 826
AED 1,771 total
includes taxes & fees
1 Dec - 2 Dec
Charming Accommodations in the Hamptons
Room

18. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (460 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is AED 500
AED 611 total
includes taxes & fees
8 Nov - 9 Nov
Montauk Oceanside Suites
A dining area with a round table, six chairs, and a chandelier.

19. 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.
The price is AED 328
AED 4,900 total
includes taxes & fees
11 Nov - 12 Nov
Year round Jacuzzi - Blackberry East Hampton Home
Living area

20. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (305 reviews)
"Staff are nice"
United States
na
The price is AED 803
AED 1,149 total
includes taxes & fees
9 Nov - 10 Nov
The Surf Club
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

Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"We love this place a lot, very beautiful beach and nice people"
Thanh 2-night trip
Posted 9 hours ago
Ocean Vista Resort

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.