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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Shelter Island Heights vacation rentals

Terrace/patio

1. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is SAR 635
SAR 1,142 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A modern house with a deck, outdoor seating, and a fire pit.

2. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (63 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is SAR 911
SAR 1,041 total
includes taxes & fees
21 Oct - 22 Oct
North Fork Resort
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, (54 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is SAR 357
SAR 927 total
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A beach with people relaxing on chairs and sunbathing.

4. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is SAR 357
SAR 931 total
includes taxes & fees
1 Nov - 2 Nov
Harbor Heights
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, (33 reviews)
"We had a great stay!! "
United States
Callie E.
The price is SAR 544
SAR 1,446 total
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

6. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is SAR 357
SAR 953 total
includes taxes & fees
9 Nov - 10 Nov
Aqua Vista
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 SAR 732
SAR 1,690 total
includes taxes & fees
3 Nov - 4 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 SAR 747
SAR 1,150 total
includes taxes & fees
12 Oct - 13 Oct
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, (1,414 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is SAR 568
SAR 722 total
includes taxes & fees
2 Nov - 3 Nov
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 SAR 1,014
SAR 2,205 total
includes taxes & fees
2 Nov - 3 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, (14 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is SAR 1,267
SAR 2,537 total
includes taxes & fees
8 Nov - 9 Nov
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, (324 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is SAR 524
SAR 701 total
includes taxes & fees
18 Oct - 19 Oct
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 SAR 1,866
SAR 3,414 total
includes taxes & fees
2 Nov - 3 Nov
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
A tent with a wooden frame, two red chairs, and a table.

14. 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.
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Room

15. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (255 reviews)
"Great right on the beach property with nice pool."
United States
Julian
The price is SAR 443
SAR 629 total
includes taxes & fees
12 Oct - 13 Oct
Driftwood Resort
A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

16. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful home, great views and host!"
United States
Kate R.
The price is SAR 2,771
SAR 4,645 total
includes taxes & fees
8 Nov - 9 Nov
Beachfront Greenport Villa
Room

17. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (456 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is SAR 532
SAR 649 total
includes taxes & fees
19 Oct - 20 Oct
Montauk Oceanside Suites
A campsite with several tents and a picnic table.

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

Safari Tent Glamping,S8-CedarPt, East Hampton, NY
East Hampton
9.6 out of 10, Exceptional, (4 reviews)
"Great time ina great place friendly and helpful staff clean cabins"
United States
Ceren B.
The price is SAR 653
SAR 1,017 total
includes taxes & fees
11 Oct - 12 Oct
Safari Tent Glamping,S8-CedarPt, East Hampton, NY
Living area

19. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (303 reviews)
"Staff are nice"
United States
na
The price is SAR 794
SAR 1,143 total
includes taxes & fees
26 Oct - 27 Oct
The Surf Club
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
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is SAR 318
SAR 695 total
includes taxes & fees
11 Oct - 12 Oct
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.
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Top Shelter Island Heights Hotel Reviews

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"All good. Beautiful relaxing time on the beach and near town. Weather fantastic! Come back every year."
Jeanne 2-night trip
Posted 12 hours ago
Montauk Blue Hotel

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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : Visitors like this Shelter Island Heights vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 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.