Photo by Erisa Dilo

Holiday Rentals in Shelter Island Heights

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Shelter Island Heights

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1238)
"I had the best time and highly recommend this hotel!"
The price is €308
includes taxes & fees
1 Sept - 2 Sept
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (405)
"great place to stay"
The price is €204
includes taxes & fees
3 Sept - 4 Sept
Montauk Oceanside Suites

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (272)
"The front desk was great !!"
The price is €376
includes taxes & fees
10 Sept - 11 Sept
The Surf Club

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great location, great views. Walls are a little thin."
The price is €362
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (291)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is €182
includes taxes & fees
14 Sept - 15 Sept
Windward Shores Ocean Resort

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

8.8 out of 10, Excellent, (26)
"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

3.5 star property
9.0 out of 10, Wonderful, (229)
"Great place to stay for small family "
The price is €228
includes taxes & fees
3 Sept - 4 Sept
Driftwood Resort

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Great place! Great communication with property owner!"
The price is €518
includes taxes & fees
7 Sept - 8 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (69)
"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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is €255
includes taxes & fees
24 Aug - 25 Aug
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Offshore Residences

4.0 star property
The price is €986
includes taxes & fees
1 Sept - 2 Sept
Offshore Residences

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (71)
"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

Canoe Place Waterfront Residences

4.0 star property
10.0 out of 10, Exceptional, (1)
Canoe Place Waterfront Residences

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

4.0 star property
9.6 out of 10, Exceptional, (134)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

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

10.0 out of 10, Exceptional, (93)
"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

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is €174
includes taxes & fees
2 Sept - 3 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (10)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is €353
includes taxes & fees
21 Aug - 22 Aug
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

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

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (29)
"Amazing property! Had all the things we needed "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"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 €226
includes taxes & fees
31 Aug - 1 Sept
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shelter Island Heights Hotel Reviews

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub 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.