A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island Vacation Rentals

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Shelter Island vacation rentals

Private kitchen

1. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (57 reviews)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
$1,151 nightly
The price is $1,315
Sep 22 - Sep 23
Total with taxes and fees
Work and Play Special! Extended Stay Discount
Condo | Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (288 reviews)
"Great place!"
United States
Christine
$380 nightly
The price is $434
Sep 21 - Sep 22
Total with taxes and fees
Cliffside Resort Condominiums
Living area

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (50 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$293 nightly
The price is $334
Sep 7 - Sep 8
Total with taxes and fees
North Fork Resort
Beach

4. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (10 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
$361 nightly
The price is $412
Sep 7 - Sep 8
Total with taxes and fees
Beach Block Hideaway
Beach

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (23 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
$304 nightly
The price is $347
Sep 3 - Sep 4
Total with taxes and fees
Harbor Heights
Terrace/patio

6. 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.
$382 nightly
The price is $436
Aug 31 - Sep 1
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Beach

7. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (49 reviews)
"House is exactly as advertised. Street traffic is a little noisier than expected being near the ferry."
United States
Kendric S.
$325 nightly
The price is $371
Sep 10 - Sep 11
Total with taxes and fees
The SandPiper
Beach

8. 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, (29 reviews)
"We had a great stay!! "
United States
Callie E.
$368 nightly
The price is $420
Sep 7 - Sep 8
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Property grounds

9. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
$285 nightly
The price is $326
Aug 30 - Aug 31
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Beach

10. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (42 reviews)
"Such a wonderful stay! Christopher was such a great host, the property matched the description, was extremely clean and situated in a perfect location just a short walk from town! Would stay again & recommend to family/friends!"
United States
Anonymous traveler
$325 nightly
The price is $371
Sep 8 - Sep 9
Total with taxes and fees
Aqua Vista
Property grounds

11. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
$285 nightly
The price is $326
Aug 30 - Aug 31
Total with taxes and fees
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Living area

12. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"We had a wonderful girls weekend in Greenport. The house was perfect for the three of us. Loved the location. We didn’t get to use the back area due to the weather, but it looked so inviting. Next time!"
United States
Melissa A.
$643 nightly
The price is $734
Sep 17 - Sep 18
Total with taxes and fees
Renovated Townhouse walk to all
Dining

13. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (7 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.
$827 nightly
The price is $944
Sep 17 - Sep 18
Total with taxes and fees
Northfork Townhouse walk to all
Living 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.
$977 nightly
The price is $1,116
Sep 14 - Sep 15
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

15. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"great"
United States
Fiona B.
$295 nightly
The price is $337
Aug 31 - Sep 1
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
Property grounds

16. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
$1,248 nightly
The price is $1,425
Sep 10 - Sep 11
Total with taxes and fees
Beachfront Greenport Villa
Property grounds

17. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
$285 nightly
The price is $326
Aug 30 - Aug 31
Total with taxes and fees
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
Room

18. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Comfortable bed and beautiful surroundings"
United States
Matthew
$285 nightly
The price is $326
Sep 7 - Sep 8
Total with taxes and fees
Safari Tent Glamping,S2-CedarPt, East Hampton, NY
Property grounds

19. Safari Tent Glamping,S11-CedarPt, East Hampton, NY

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"Our tent was spacious and the bed was very comfortable with an incredible view of the harbor. Dave and Lee were very gracious and helpful. We especially enjoyed the Camp Store and the delicious omelets. Plus - how quiet and peaceful it was!"
United States
Lee
$259 nightly
The price is $296
Aug 27 - Aug 28
Total with taxes and fees
Safari Tent Glamping,S11-CedarPt, East Hampton, NY
Property grounds

20. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (4 reviews)
"First time glamping with my boys and had a great time."
United States
Massimo P.
$295 nightly
The price is $337
Aug 30 - Aug 31
Total with taxes and fees
Safari Tent Glamping,D28-CedarPt, East Hampton, NY
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

Sound View Greenport

Sound View Greenport

8/10 Good
"The hotel was lovely and right on the Long Island Sound. The view was great. The room was comfortable. For the price you will pay per night, there should have been more added touches. They should provide robes and extra towels, etc. Upon check in, no one greeted us warmly or assisted in telling us where our room was. And there was not enough parking for our car. The restaurant at the hotel was excellent. All in all, it was a nice stay, but not worth the high cost."
Leslie J 2-night trip
Posted 5 hours ago
Sound View Greenport

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 $222 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?

The Hampton Sack a cheerful relaxing beach cottage: This vacation home rental near Shelter Island is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Shelter Island?

Choose from 90 Expedia vacation rentals in Shelter Island for a memorable vacation.

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. Shelter Island Historical Society and Mashomack Preserve 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.