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Shelter Island Heights Holiday Rentals

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Check prices for these dates

Tonight
26 July - 27 July
Tomorrow
27 July - 28 July
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Holiday Rentals in Shelter Island Heights

Montauk Manor
Stunning multi-story building with a traditional design, featuring balconies and a beautifully manicured lawn.

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1220)
"Great hotel"
The price is AU$836
includes taxes & fees
28 July - 29 July
Montauk Manor
The Surf Club
Relax on the beach with comfortable lounge chairs and umbrellas, surrounded by serene ocean views.

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (264)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is AU$1,060
includes taxes & fees
28 July - 29 July
The Surf Club
Montauk Oceanside Suites
Cozy living space with a dining table, sofa, and kitchenette, complete with a stove and refrigerator.

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (397)
"Loved it, amazing area & spacious room. "
The price is AU$618
includes taxes & fees
28 July - 29 July
Montauk Oceanside Suites
Windward Shores Ocean Resort
Enjoy a panoramic ocean view from the comfort of this room, featuring a dining table, seating area, and sliding glass doors to the outdoor patio.

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (289)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is AU$778
includes taxes & fees
28 July - 29 July
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Stunning beachfront residential area with multi-story buildings and a central park.

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (229)
"Great property overall with beautiful grounds, a pool and access to the beach. Condos are spacious and equipped with bathroom and kitchen items. Ours had a patio with a great view of the water! We will definitely stay here again. "
The price is AU$651
includes taxes & fees
29 July - 30 July
Cliffside Resort Condominiums
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Relax in this stylish living space with a sofa, two chairs, and a small table, leading to an outdoor area through a large sliding door.

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Driftwood Resort
Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (226)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is AU$949
includes taxes & fees
28 July - 29 July
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (9)
"Great place! Great communication with property owner!"
The price is AU$965
includes taxes & fees
28 July - 29 July
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Hamptons Retreat
Terrace/patio

Hamptons Retreat

Hamptons Retreat
The Stern at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with access to the ocean and a sailboat visible in the distance.

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (2)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$303
includes taxes & fees
30 July - 31 July
The Stern at Soundview · Beach+Ocean+Sunrise
NORTHFORK COTTAGE with POOL & HOT TUB
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB

4.0 star property
9.6 out of 10, Exceptional, (131)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB
Fairy Tale Guest Cottage in Magic Garden by Pool
Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (70)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool
Sag Harbor Suite by the Beach
Simple, functional room with a single bed and a window with curtains.

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Relax in this spacious living area with a high ceiling, large windows offering views of the surrounding trees, and a comfortable seating arrangement.

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (90)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Walk to town, Bike to beach, Private pool oasis !
Relax by the serene pool surrounded by lush greenery.

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !
Shoreline Oasis
Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

Shoreline Oasis

9.0 out of 10, Wonderful, (4)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$404
includes taxes & fees
28 July - 29 July
Shoreline Oasis
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is AU$955
includes taxes & fees
28 July - 29 July
Southampton cozy cottage by the beach
The Anchor at Soundview · Beach+Ocean+Sunrise
Enjoy a serene beach experience with access to the ocean and a picturesque sailboat in the distance.

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.0 out of 10, Very good, (1)
"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "
The price is AU$343
includes taxes & fees
27 Aug - 28 Aug
The Anchor at Soundview · Beach+Ocean+Sunrise
Perfect Mid-Century Private Waterfront East Hampton Retreat!
Enjoy a serene meal on the deck overlooking the tranquil waters of East Hampton, New York.

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!
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

The Montauk Soundview

The Montauk Soundview

10/10 Excellent
"Great clean accommodations close to everything. "
howard 2-night trip
Posted 8 hours ago
The Montauk Soundview

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?

Hamptons Retreat: This holiday home rental outside of Shelter Island Heights offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island Heights?

With 47 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.