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

Shelter Island Holiday Rentals

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Our top choices for Shelter Island holiday rentals

1. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, 58, (58 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
The price is AU$1,804
includes taxes & fees
15 Sept - 16 Sept
Work and Play Special! Extended Stay Discount

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

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, 2, (2 reviews)
"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
The price is AU$409
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, 54, (54 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AU$478
includes taxes & fees
15 Sept - 16 Sept
North Fork Resort

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, 292, (292 reviews)
"Great place!"
United States
Christine
The price is AU$585
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, 10, (10 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
United States
Teresa C.
The price is AU$565
includes taxes & fees
15 Sept - 16 Sept
Beach Block Hideaway

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, 45, (45 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$446
includes taxes & fees
7 Oct - 8 Oct
Aqua Vista

7. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, 26, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is AU$441
includes taxes & fees
5 Oct - 6 Oct
Harbor Heights

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, 31, (31 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$576
includes taxes & fees
15 Sept - 16 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

9. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, 52, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AU$489
includes taxes & fees
28 Sept - 29 Sept
The SandPiper

10. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, 6, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is AU$494
includes taxes & fees
16 Sept - 17 Sept
American Beech in Greenport - Petite King Room 7

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, 2, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is AU$452
includes taxes & fees
20 Sept - 21 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

12. BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.2 out of 10, 7, (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 AU$1,745
includes taxes & fees
15 Sept - 16 Sept
BlackBerry Private home with jacuzzi yearlong

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

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, 5, (5 reviews)
"It was a really great experience! We barbecued and made a camp fire. Took a walk on the beach. Played in the playground. The pizza and breakfast sandwiches in the café were delicious! We will definitely be coming back!"
United States
Brian F.
The price is AU$427
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

14. Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.4 out of 10, 6, (6 reviews)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
United States
Lorraine
The price is AU$452
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,S6-CedarPt, East Hampton, NY

15. Safari Tent Glamping,D26-CedarPt, East Hampton, NY

Safari Tent Glamping,D26-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, 1, (1 review)
"This campground is a pleasant and relaxing place to spend a few days. I love to sit by the fire pit and look out on the water. The new on site pizza place was delicious."
United States
Melissa
The price is AU$466
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,D26-CedarPt, East Hampton, NY

16. Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, 14, (14 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.
Renovated Townhouse walk to all

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

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, 4, (4 reviews)
"great"
United States
Fiona B.
The price is AU$427
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,D27-CedarPt, East Hampton, NY

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

Safari Tent Glamping,S2-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, 2, (2 reviews)
"Outstanding place"
United States
Michael H.
The price is AU$452
includes taxes & fees
17 Sept - 18 Sept
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

19. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, 1, (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 AU$766
includes taxes & fees
15 Sept - 16 Sept
Lovely studio with AC in charming Sag Harbor

20. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, 8, (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.
Northfork Townhouse walk to all
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

Find out more about Shelter Island

Everything you need to know about Shelter Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Shelter Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as AU$227 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Shelter Island is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 holiday rentals are there in Shelter Island?

Choose from 86 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Mashomack Preserve 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 Crescent Beach are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.