A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Shelter Island Heights vacation rentals

Condo | Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (279 reviews)
"Great place!"
United States
Christine
$452 nightly
The price is $516
Aug 5 - Aug 6
Total with taxes and fees
Cliffside Resort Condominiums
Sun loungers, beach towels

2. Aqua Vista

Aqua Vista
Pipes Cove
9.8 out of 10, Exceptional, (40 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
$336 nightly
The price is $384
Sep 1 - Sep 2
Total with taxes and fees
Aqua Vista
Flat-screen TV

3. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
$598 nightly
The price is $683
Aug 10 - Aug 11
Total with taxes and fees
North Fork Resort
Terrace/patio

4. 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.
$485 nightly
The price is $554
Aug 10 - Aug 11
Total with taxes and fees
American Beech in Greenport - Petite King Room 7
Beach

5. 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
$452 nightly
The price is $516
Sep 3 - Sep 4
Total with taxes and fees
Harbor Heights
Sun loungers, beach towels

6. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
$521 nightly
The price is $595
Aug 16 - Aug 17
Total with taxes and fees
The SandPiper
Sun loungers, beach towels

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, (28 reviews)
"We had a great stay!! "
United States
Callie E.
$680 nightly
The price is $777
Aug 26 - Aug 27
Total with taxes and fees
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
1 bedroom, bed sheets

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

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
$296 nightly
The price is $338
Aug 19 - Aug 20
Total with taxes and fees
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
1 bedroom, bed sheets

9. 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
$260 nightly
The price is $298
Aug 6 - Aug 7
Total with taxes and fees
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
1 bedroom, bed sheets

10. 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
$285 nightly
The price is $326
Aug 10 - Aug 11
Total with taxes and fees
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
1 bedroom, desk, iron/ironing board, travel crib

11. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (51 reviews)
"We enjoyed our stay"
United States
JM B.
$215 nightly
The price is $244
Sep 1 - Sep 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, books

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.
$1,310 nightly
The price is $1,497
Sep 2 - Sep 3
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
1 bedroom, bed sheets

13. 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
$259 nightly
The price is $296
Aug 5 - Aug 6
Total with taxes and fees
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Beach nearby

14. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$251 nightly
The price is $283
Aug 5 - Aug 6
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
1 bedroom, bed sheets

15. 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
$260 nightly
The price is $298
Aug 5 - Aug 6
Total with taxes and fees
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
1 bedroom, bed sheets

16. 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
$260 nightly
The price is $298
Aug 6 - Aug 7
Total with taxes and fees
Safari Tent Glamping,S9-CedarPt, East Hampton, NY
Property grounds

17. 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
$530 nightly
The price is $606
Aug 10 - Aug 11
Total with taxes and fees
American Beech in Greenport - Deluxe King 6
1 bedroom, bed sheets

18. Safari Tent Glamping,S3-CedarPt, East Hampton, NY

Safari Tent Glamping,S3-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (3 reviews)
"The store was great and the upgrades were perfect. The pizza was excellent and hope to be back soon"
United States
Joseph
$285 nightly
The price is $326
Aug 13 - Aug 14
Total with taxes and fees
Safari Tent Glamping,S3-CedarPt, East Hampton, NY
1 bedroom, bed sheets

19. 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.
$296 nightly
The price is $338
Aug 11 - Aug 12
Total with taxes and fees
Safari Tent Glamping,D28-CedarPt, East Hampton, NY
Coffee/tea maker, fridge, microwave, oven

20. New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Greenport
10.0 out of 10, Exceptional, (4 reviews)
"Great location and beautiful inside!"
United States
Lauren H.
$1,725 nightly
The price is $1,971
Aug 9 - Aug 10
Total with taxes and fees
New Construction Greenport Pool House - 3 Blocks from Town
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 Heights Hotel Reviews

Montauk Manor

Montauk Manor

10/10 Excellent
"Overall a great experience coming back because of the berky the room manager and janice the hotel manager. I had a couple of issues and they were very apologetic and did the right thing. I appreciate the room switch and compensation!"
Laura A 2-night trip
Posted 8 hours ago
Montauk Manor

Find out more about Shelter Island Heights

Everything you need to know about Shelter Island Heights 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 Heights 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 Heights vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island Heights vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island Heights. 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 Heights 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 $244 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 Heights rentals

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

Are there vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Shelter Island Heights. Make sure you have time to check out the golf courses and entertainment choices during your trip.

What's the top vacation rental that Shelter Island Heights has to offer?

Cozy sun drenched beach cottage private beach & hot tub. Walk 2 town & Gurneys.: Visitors like this Shelter Island Heights vacation home rental. It is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals are there in Shelter Island Heights?

With 32 Expedia vacation rentals, you're sure to find just the right place for your Shelter Island Heights stay.

What’s there to see and do in Shelter Island Heights?

Sunset Beach and Crescent Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shelter Island Country Club and Sylvester Manor.

What’s a vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.