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Shelter Island Holiday Rentals

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Our top choices for Shelter Island holiday rentals

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (41 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is AU$820
includes taxes & fees
17 Aug - 18 Aug
North Fork Resort

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (277 reviews)
"Quiet, clean, good hospitality, private beach."
United States
Nitinun
The price is AU$673
includes taxes & fees
5 Aug - 6 Aug
Cliffside Resort Condominiums

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"⭐⭐⭐⭐⭐ 100/10 – An unforgettable romantic getaway! We had an amazing stay at this glamping site and spent two wonderful, romantic days here. The atmosphere was peaceful, cozy, and incredibly relaxing. Surrounded by nature, we enjoyed the fresh air, breathtaking sunsets, and quiet evenings that created memories we’ll always cherish. Everything was clean, comfortable, and thoughtfully prepared. The staff was exceptionally kind, welcoming, and always ready to help, which made our stay even more...
United States
Malika
The price is AU$417
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

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

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.2 out of 10, Wonderful, (5 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$459
includes taxes & fees
12 Aug - 13 Aug
Safari Tent Glamping,S6-CedarPt, East Hampton, NY

5. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (7 reviews)
"Everything was so nice and clean. Location was great, walking distance from everything. My children had an amazing time. I would book this again in the summer."
United States
Jessica0610@gmail.com A.
Beach Block Hideaway

6. Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is AU$422
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

7. The SandPiper

The SandPiper
Pipes Cove
9.8 out of 10, Exceptional, (44 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is AU$918
includes taxes & fees
16 Aug - 17 Aug
The SandPiper

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, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$1,084
includes taxes & fees
26 Aug - 27 Aug
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

9. Harbor Heights

Harbor Heights
Pipes Cove
9.8 out of 10, Exceptional, (19 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is AU$837
includes taxes & fees
12 Aug - 13 Aug
Harbor Heights

10. 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)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is AU$716
includes taxes & fees
2 Aug - 3 Aug
American Beech in Greenport - Petite King Room 7

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

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 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
The price is AU$466
includes taxes & fees
30 Aug - 31 Aug
Safari Tent Glamping,S11-CedarPt, East Hampton, NY

12. 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.
The price is AU$440
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

13. Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (39 reviews)
"great anf friendly, clean"
United States
Sophia
The price is AU$896
includes taxes & fees
30 Aug - 31 Aug
Aqua Vista

14. 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
The price is AU$422
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S2-CedarPt, East Hampton, NY

15. 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
The price is AU$422
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S7-CedarPt, East Hampton, NY

16. Safari Tent Glamping,S8-CedarPt, East Hampton, NY

Safari Tent Glamping,S8-CedarPt, East Hampton, NY
East Hampton
9.4 out of 10, Exceptional, (3 reviews)
"From the friendly staff and ease at check-in, to the super comfortable amenities, and the water view from your tent that you just can't beat, this place and this experience were absolutely amazing. I will be back!"
United States
Christopher
The price is AU$422
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S8-CedarPt, East Hampton, NY

17. Safari Tent Glamping,D30-CedarPt, East Hampton, NY

Safari Tent Glamping,D30-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Live music, small bar, pizza and friendly staff."
United States
Bibek
The price is AU$470
includes taxes & fees
13 Aug - 14 Aug
Safari Tent Glamping,D30-CedarPt, East Hampton, NY

18. Safari Tent Glamping,S9-CedarPt, East Hampton, NY

Safari Tent Glamping,S9-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"It was relaxing and beautiful - a perfect and affordable getaway from the city! Also great proximity to so many fun things."
United States
Carolyn
The price is AU$422
includes taxes & fees
2 Aug - 3 Aug
Safari Tent Glamping,S9-CedarPt, East Hampton, NY

19. Safari Tent Glamping,D29-CedarPt, East Hampton, NY

Safari Tent Glamping,D29-CedarPt, East Hampton, NY
East Hampton
8.0 out of 10, Very good, (1 review)
"If you upgrade the bathroom and shower facilities for glamping only- even if you increase the rate to stay- that would make it a true glamping experience. Willing to pay extra for better bathrooms and showers. Consider renting fancy bathroom and showers and increasing your prices. Thank you. Other than that it was wonderful."
United States
Aurelia
The price is AU$470
includes taxes & fees
11 Aug - 12 Aug
Safari Tent Glamping,D29-CedarPt, East Hampton, NY

20. Safari Tent Glamping,S1-CedarPt, East Hampton, NY

Safari Tent Glamping,S1-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"We loved it and will be back!!"
United States
Bonnie
The price is AU$466
includes taxes & fees
31 Aug - 1 Sept
Safari Tent Glamping,S1-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

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$361 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?

Bright and Spacious Summer Home Steps from the Beach: This highly rated holiday home rental in Shelter Island is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Shelter Island?

Choose from 91 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Wades 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 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.