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Shelter Island Heights Holiday Rentals

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Check prices for these dates

Tonight
27 Jun - 28 Jun
Tomorrow
28 Jun - 29 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Holiday Rentals in Shelter Island Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1200)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is NZ$722
includes taxes & fees
29 June - 30 June
Montauk Manor
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is NZ$546
includes taxes & fees
29 June - 30 June
Windward Shores Ocean Resort
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (383)
"great place to stay"
The price is NZ$499
includes taxes & fees
2 July - 3 July
Montauk Oceanside Suites
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (224)
"The staff was very friendly I will definitely be back again 👍"
The price is NZ$897
includes taxes & fees
6 July - 7 July
Driftwood Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (259)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is NZ$724
includes taxes & fees
10 July - 11 July
The Surf Club
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (223)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is NZ$494
includes taxes & fees
9 July - 10 July
Cliffside Resort Condominiums
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
The price is NZ$3,790
includes taxes & fees
6 July - 7 July
Canoe Place Waterfront Residences
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"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
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

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
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Exterior

COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎

10.0 out of 10, Exceptional, (34)
"My wife and I loved our weekend stay at this cabin!"
The price is NZ$1,156
includes taxes & fees
28 June - 29 June
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach
A heated pool

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (83)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach
Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton
Smart TV, fireplace

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton
Charming Montauk Getaway centrally located
Beach nearby

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (45)
"Quiet, private, well-appointed spot with everything you need for a getaway. Conveniently located within walking distance to town, it has its own outdoor area perfect for lounging and cooking out. We loved it!"
Charming Montauk Getaway centrally located
Shoreline Oasis
Exterior

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is NZ$430
includes taxes & fees
6 July - 7 July
Shoreline Oasis
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is NZ$364
includes taxes & fees
2 July - 3 July
Freeboard at Soundview · Beach+Ocean+Sunrise
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Smart TV, fireplace, stereo

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

10.0 out of 10, Exceptional, (86)
"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
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Terrace/patio

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
Beach nearby, sun-loungers

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

9.6 out of 10, Exceptional, (44)
"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard
Outdoor pool, a heated pool

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is NZ$1,571
includes taxes & fees
27 July - 28 July
Southampton cozy cottage by the beach
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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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?

3-bedroom Montauk Coastal Getaway: This holiday home rental outside of Shelter Island Heights offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

How many holiday rentals are there in Shelter Island Heights?

With 34 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.