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Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Shelter Island vacation rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is ￥26,734
￥48,092 total
includes taxes & fees
Nov 15 - Nov 16
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (69 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is ￥47,432
￥54,191 total
includes taxes & fees
Oct 25 - Oct 26
North Fork Resort
A wooden pathway leading to a beach with scattered rocks and greenery.

3. 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 ￥30,843
￥71,198 total
includes taxes & fees
Nov 3 - Nov 4
Beach Block Hideaway
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is ￥15,026
￥40,118 total
includes taxes & fees
Nov 17 - Nov 18
Aqua Vista
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

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 ￥15,037
￥40,329 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper
A beach with people relaxing on chairs and sunbathing.

6. 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 ￥13,524
￥38,403 total
includes taxes & fees
Nov 3 - Nov 4
Harbor Heights
A beach with people relaxing, a pier extending into the water, and a clear sky.

7. 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 wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is ￥20,641
￥56,109 total
includes taxes & fees
Nov 3 - Nov 4
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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 ￥31,476
￥48,432 total
includes taxes & fees
Oct 25 - Oct 26
American Beech in Greenport - Petite King Room 7
A modern dining area with a wooden table, white chairs, and a chandelier.

9. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (8 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 ￥49,146
￥101,358 total
includes taxes & fees
Nov 10 - Nov 11
Northfork Townhouse walk to all
A spacious hallway with high ceilings, arched columns, and chandeliers.

10. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,417 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ￥23,118
￥29,510 total
includes taxes & fees
Nov 17 - Nov 18
Montauk Manor
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.

11. 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 ￥43,448
￥93,942 total
includes taxes & fees
Nov 4 - Nov 5
Renovated Townhouse walk to all
A modern living room with a sofa, coffee table, and dining area.

12. 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 ￥74,866
￥137,615 total
includes taxes & fees
Nov 17 - Nov 18
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Room

13. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (331 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 ￥22,577
￥30,095 total
includes taxes & fees
Oct 25 - Oct 26
Windward Shores Ocean Resort
Room

14. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (256 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is ￥21,668
￥29,907 total
includes taxes & fees
Oct 25 - Oct 26
Driftwood Resort
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 ￥35,588
￥82,583 total
includes taxes & fees
Nov 10 - Nov 11
Lovely studio with AC in charming Sag Harbor
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

16. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is ￥100,429
￥174,417 total
includes taxes & fees
Nov 10 - Nov 11
Beachfront Greenport Villa
A dining area with a round table, six chairs, and a chandelier.

17. 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 ￥10,597
￥199,958 total
includes taxes & fees
Oct 25 - Oct 26
Year round Jacuzzi - Blackberry East Hampton Home
Room

18. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (457 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is ￥22,421
￥27,337 total
includes taxes & fees
Oct 25 - Oct 26
Montauk Oceanside Suites
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

19. 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 ￥85,198
￥183,540 total
includes taxes & fees
Oct 23 - Oct 24
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

20. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥19,360
￥36,792 total
includes taxes & fees
Oct 29 - Oct 30
1-bedroom cottage with Grove Beach 🏖️ access.
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Great"
allison 3-night trip
Posted 4 hours ago
Water's Edge Resort & Spa

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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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.