Photo by Erisa Dilo

Shelter Island Heights Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21
In four months
Jan 16 - Jan 18

Vacation Rentals in Shelter Island Heights

The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (77)
"Shelter Island is definitely a gem"
The Pridwin Hotel
The Chequit
Exterior

The Chequit

3.0 star property
9.0 out of 10, Wonderful, (36)
"Everyone was amazing "
The Chequit
Shelter Island House
Property grounds

Shelter Island House

3.5 star property
8.4 out of 10, Very Good, (56)
"We liked the areas for sitting outside, to sit with a coffee, talk and relax. It was convenient to have a fridge. A very different accommodation but typical for the island. We enjoyed our stay!"
The price is ￥29,950
￥34,217 total
includes taxes & fees
Sep 28 - Sep 29
Shelter Island House
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (37)
"Great property! Close to beach and super clean. "
The price is ￥46,655
￥53,304 total
includes taxes & fees
Oct 2 - Oct 3
West Neck Guesthouse
White Oak Cottage | The Pridwin Hotel and Cottages
A heated pool

White Oak Cottage | The Pridwin Hotel and Cottages

White Oak Cottage | The Pridwin Hotel and Cottages
The Rams Head Inn
Exterior

The Rams Head Inn

4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
The Rams Head Inn
Larch Cottage | The Pridwin Hotel and Cottages
A heated pool

Larch Cottage | The Pridwin Hotel and Cottages

Larch Cottage | The Pridwin Hotel and Cottages
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (76)
"It was a peaceful and serene as it gets what a nice overnight stay we will have to come back again to explore more sometime soon. "
The price is ￥32,038
￥36,604 total
includes taxes & fees
Oct 2 - Oct 3
House on Chase Creek
Hickory Cottage | The Pridwin Hotel and Cottages
A heated pool

Hickory Cottage | The Pridwin Hotel and Cottages

Hickory Cottage | The Pridwin Hotel and Cottages
Corner Preferred Room | The Pridwin Hotel and Cottages
A heated pool

Corner Preferred Room | The Pridwin Hotel and Cottages

Corner Preferred Room | The Pridwin Hotel and Cottages
Birch Cottage | The Pridwin Hotel and Cottages
A heated pool

Birch Cottage | The Pridwin Hotel and Cottages

Birch Cottage | The Pridwin Hotel and Cottages
Caroline Cottage | The Pridwin Hotel and Cottages
A heated pool

Caroline Cottage | The Pridwin Hotel and Cottages

Caroline Cottage | The Pridwin Hotel and Cottages
Terrace Room | The Pridwin Hotel and Cottages
A heated pool

Terrace Room | The Pridwin Hotel and Cottages

Terrace Room | The Pridwin Hotel and Cottages
Red Oak Cottage | The Pridwin Hotel and Cottages
A heated pool

Red Oak Cottage | The Pridwin Hotel and Cottages

Red Oak Cottage | The Pridwin Hotel and Cottages
Fraser Cottage | The Pridwin Hotel and Cottages
A heated pool

Fraser Cottage | The Pridwin Hotel and Cottages

Fraser Cottage | The Pridwin Hotel and Cottages
SEVEN - Shelter Island Guest House
Kayaking

SEVEN - Shelter Island Guest House

2.5 star property
9.8 out of 10, Exceptional, (57)
"It was a beautiful place! Under construction however, Beth was Amazing! Amelia was so hospitable. Close to everything and it certainly helped that the weather was spectacular! Will definitely go back another time!"
SEVEN - Shelter Island Guest House
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

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

10/10 Excellent
"The rooms were super clean,comfortable and inviting! Would definitely stay again!"
wendy 1-night trip
Posted 12 hours ago
Best Western Niantic - New London/Mystic Area

Find out more about Shelter Island Heights

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 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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : Visitors like this Shelter Island Heights vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island Heights?

With 34 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.