A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Shelter Island Heights holiday 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, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is HK$1,326
HK$2,385 total
includes taxes & fees
15 Nov - 16 Nov
Cliffside Resort Condominiums
A train station platform with a shelter, a sign reading "Greenport," and multiple railway tracks.

2. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is HK$671
HK$1,806 total
includes taxes & fees
8 Nov - 9 Nov
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, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is HK$671
HK$1,806 total
includes taxes & fees
10 Nov - 11 Nov
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, (52 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is HK$745
HK$1,901 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is HK$1,024
HK$2,730 total
includes taxes & fees
4 Nov - 5 Nov
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, (72 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is HK$2,521
HK$2,880 total
includes taxes & fees
4 Nov - 5 Nov
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.
The price is HK$1,530
HK$3,362 total
includes taxes & fees
4 Nov - 5 Nov
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.
The price is HK$1,561
HK$2,277 total
includes taxes & fees
4 Nov - 5 Nov
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, (1,419 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is HK$1,087
HK$1,396 total
includes taxes & fees
30 Nov - 1 Dec
Montauk Manor
A modern dining area with a wooden table, white chairs, and a chandelier.

10. Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (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.
The price is HK$1,871
HK$4,290 total
includes taxes & fees
4 Nov - 5 Nov
Northfork Townhouse walk to all
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.

11. 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.
The price is HK$1,801
HK$4,200 total
includes taxes & fees
1 Dec - 2 Dec
Renovated Townhouse walk to all
Room

12. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (332 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
The price is HK$1,034
HK$1,394 total
includes taxes & fees
5 Nov - 6 Nov
Windward Shores Ocean Resort
A modern living room with a sofa, coffee table, and dining area.

13. 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.
The price is HK$3,484
HK$6,267 total
includes taxes & fees
10 Nov - 11 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

14. 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
The price is HK$1,797
HK$2,573 total
includes taxes & fees
4 Nov - 5 Nov
American Beech in Greenport - Deluxe King 6
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

15. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is HK$3,425
HK$6,620 total
includes taxes & fees
10 Nov - 11 Nov
Beachfront Greenport Villa
Room

16. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.4 out of 10, Very good, (460 reviews)
"The room was very clean and well taken care of."
United States
Mitchell
The price is HK$1,068
HK$1,305 total
includes taxes & fees
10 Nov - 11 Nov
Montauk Oceanside Suites
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
The price is HK$1,765
HK$3,899 total
includes taxes & fees
10 Nov - 11 Nov
Charming Accommodations in the Hamptons
A dining area with a round table, six chairs, and a chandelier.

18. Year round Jacuzzi - Blackberry East Hampton Home

Year round Jacuzzi - Blackberry East Hampton Home
East Hampton
9.2 out of 10, Wonderful, (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 HK$755
HK$10,313 total
includes taxes & fees
8 Nov - 9 Nov
Year round Jacuzzi - Blackberry East Hampton Home
A beach with footprints leading to the water, a sunset in the background, and a clear sky.

19. Walk to Beach | Seabreeze Cottage #4

Walk to Beach | Seabreeze Cottage #4
Hampton Bays
8.8 out of 10, Excellent, (9 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is HK$643
HK$3,772 total
includes taxes & fees
30 Nov - 1 Dec
Walk to Beach | Seabreeze Cottage #4
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

20. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.8 out of 10, Exceptional, (66 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$1,036
HK$1,841 total
includes taxes & fees
4 Nov - 5 Nov
1-bedroom cottage with Grove Beach 🏖️ access.
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 Heights Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Very well designed"
Alexander 2-night trip
Posted 5 hours ago
Sound View Greenport

Find out more about Shelter Island Heights

Search for holiday rentals in Shelter Island Heights on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island Heights using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island Heights
  • Use the map to find apartments and other holiday homes in the Shelter Island Heights neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island Heights while they last

Look no further and take a look at our great range of rental properties in Shelter Island Heights!

Frequently asked questions

Are there holiday rentals in Shelter Island Heights?

Yes, there are holiday rentals close to the most popular sights in Shelter Island Heights, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Shelter Island Heights has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Shelter Island Heights 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 Heights?

With 32 Expedia holiday rentals, you're guaranteed 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 holiday rental in Shelter Island Heights like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shelter Island Heights. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.