Lodging Image

Shelter Island Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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, (300 reviews)
"Great condo. Very nice location and grounds."
United States
William
$301 nightly
The price is $344
Nov 29 - Nov 30
Total with taxes and fees
Cliffside Resort Condominiums
A beach with people relaxing on chairs and sunbathing.

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.
$201 nightly
The price is $229
Nov 22 - Nov 23
Total with taxes and fees
Harbor Heights
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

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.
$203 nightly
The price is $232
Nov 30 - Dec 1
Total with taxes and fees
The SandPiper
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, (54 reviews)
"Great property and location. So easily walkable to everything. The host was super responsive, we had a great stay!"
United States
Carey D.
$210 nightly
The price is $240
Nov 18 - Nov 19
Total with taxes and fees
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

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.
$305 nightly
The price is $348
Nov 16 - Nov 17
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A modern house with a deck, outdoor seating, and a fire pit.

6. 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
$302 nightly
The price is $345
Nov 20 - Nov 21
Total with taxes and fees
North Fork Resort
A wooden pathway leading to a beach with scattered rocks and greenery.

7. 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.
$375 nightly
The price is $428
Nov 15 - Nov 16
Total with taxes and fees
Beach Block Hideaway
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.
$252 nightly
The price is $288
Nov 15 - Nov 16
Total with taxes and fees
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, (1,425 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
$156 nightly
The price is $178
Nov 30 - Dec 1
Total with taxes and fees
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.

10. 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.
$494 nightly
The price is $564
Nov 15 - Nov 16
Total with taxes and fees
Renovated 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
$170 nightly
The price is $194
Nov 15 - Nov 16
Total with taxes and fees
Windward Shores Ocean Resort
A modern dining area with a wooden table, white chairs, and a chandelier.

12. 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.
$520 nightly
The price is $594
Nov 15 - Nov 16
Total with taxes and fees
Northfork 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.
$414 nightly
The price is $473
Nov 23 - Nov 24
Total with taxes and fees
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
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.
$532 nightly
The price is $608
Nov 15 - Nov 16
Total with taxes and fees
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Room

15. 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
$146 nightly
The price is $166
Nov 29 - Nov 30
Total with taxes and fees
Montauk Oceanside Suites
A modern living room with a sofa, coffee table, and dining area.

16. 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.
$724 nightly
The price is $827
Dec 1 - Dec 2
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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
$434 nightly
The price is $496
Nov 16 - Nov 17
Total with taxes and fees
Charming Accommodations in the Hamptons
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

18. 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
$298 nightly
The price is $340
Nov 15 - Nov 16
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

19. Steps to the beach | Seabreeze Cottage #3

Steps to the beach | Seabreeze Cottage #3
Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils. The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off. The last straw was the huge spider that jumped down from the closet onto me. We ended up leaving after less than 24 hours and...
United States
Lydia
$429 nightly
The price is $454
Nov 22 - Nov 23
Total with taxes and fees
Steps to the beach | Seabreeze Cottage #3
A brick patio with outdoor seating, a wooden staircase, and a house with a window and door.

20. Cozy Cottage by the beach - Seabreeze #1

Cozy Cottage by the beach - Seabreeze #1
Hampton Bays
$423 nightly
The price is $448
Nov 21 - Nov 22
Total with taxes and fees
Cozy Cottage by the beach - Seabreeze #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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Perfect"
Thomas 1-night trip
Posted 2 hours ago
Gurney's Montauk Resort & Seawater Spa

Find out more about Shelter Island

Everything you need to know about Shelter Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.