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Shelter Island Heights Holiday Rentals

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Check prices for these dates

Tonight
6 Aug - 7 Aug
Tomorrow
7 Aug - 8 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 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, (1225)
"Nice historic place"
The price is AU$555
includes taxes & fees
1 Sept - 2 Sept
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, (268)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is AU$678
includes taxes & fees
20 Aug - 21 Aug
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, (400)
"great place to stay"
The price is AU$407
includes taxes & fees
4 Sept - 5 Sept
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, (290)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is AU$415
includes taxes & fees
3 Sept - 4 Sept
Windward Shores Ocean Resort
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
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, (233)
"Great location, great views. Walls are a little thin."
The price is AU$661
includes taxes & fees
14 Aug - 15 Aug
Cliffside Resort Condominiums
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, (227)
"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$488
includes taxes & fees
3 Sept - 4 Sept
Driftwood Resort
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
9.8 out of 10, Exceptional, (12)
"Great place! Great communication with property owner!"
The price is AU$1,105
includes taxes & fees
7 Aug - 8 Aug
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
Outdoor spa tub

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (133)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day
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
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 !
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$339
includes taxes & fees
27 Aug - 28 Aug
The Stern at Soundview · Beach+Ocean+Sunrise
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Stunning corridor with arches and columns, featuring traditional lighting fixtures and lush greenery.

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (68)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT
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, (91)
"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
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is AU$1,916
includes taxes & fees
14 Aug - 15 Aug
Southampton cozy cottage by the beach
Charming Montauk Getaway centrally located
Enjoy sunbathing and relaxation on this popular beach with umbrellas and beach chairs.

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (49)
"Mary was an amazing host! The apartment was cozy, quiet and very clean. The private fenced in yard in the back was a plus. Minutes drive to everywhere Montauk. Would stay again hands down. "
Charming Montauk Getaway centrally located
adorable ranch in beach community
Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

adorable ranch in beach community

10.0 out of 10, Exceptional, (45)
"Close to the shore and the heart of Old Saybrook. The house is very comfortable."
The price is AU$1,010
includes taxes & fees
13 Aug - 14 Aug
adorable ranch in beach community
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Surrounded by lush greenery, this cabin features a cozy porch with seating and a stone pathway leading to the entrance.

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

10.0 out of 10, Exceptional, (39)
"My wife and I loved our weekend stay at this cabin!"
The price is AU$979
includes taxes & fees
25 Aug - 26 Aug
COZY Maple Tree Cabin - Situated on 6 private acres - short drive to beaches!😎
Shoreline Oasis
Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

Shoreline Oasis

8.8 out of 10, Excellent, (5)
"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$407
includes taxes & fees
7 Aug - 8 Aug
Shoreline Oasis
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread to the pool area. July is expensive but it was definitely worth it. We live on Long Island and didn't have to deal with flying issues. Just a 2 hour drive and 4 days of relaxing sun....."
Brian 3-night trip
Posted 1 day ago
Sound View Greenport

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.