Shelter Island Heights Vacation Rentals from ￥13,824: Search Short-Term Rentals

Q: What's the top vacation rental that Shelter Island Heights has to offer?

Hamptons Retreat : 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. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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Vacation Rentals in Shelter Island Heights

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

"Nice historic place"

￥52,737 total

includes taxes & fees

Sep 1 - Sep 2

Relax on the beach with comfortable lounge chairs and umbrellas, surrounded by serene ocean views.

"Quiet, relaxing place to stay, great access to the beach and town!"

￥64,461 total

includes taxes & fees

Sep 3 - Sep 4

Cozy living space with a dining table, sofa, and kitchenette, complete with a stove and refrigerator.

"great place to stay"

￥34,913 total

includes taxes & fees

Sep 3 - Sep 4

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.

"Easy checking in and out Easy access few steps to beach from first floor unit "

￥39,461 total

includes taxes & fees

Sep 3 - Sep 4

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.

"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!...

Stunning beachfront residential area with multi-story buildings and a central park.

"Great location, great views. Walls are a little thin."

￥68,521 total

includes taxes & fees

Sep 1 - Sep 2

Enjoy cooking in this well-equipped kitchen with a tiled backsplash and black refrigerator.

"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."

￥46,381 total

includes taxes & fees

Sep 3 - Sep 4

Relax by the serene pool surrounded by tall trees and a well-maintained lawn.

"Great place! Great communication with property owner!"

￥88,810 total

includes taxes & fees

Sep 7 - Sep 8

"Loved our stay and will be back"

Relax by the serene pool surrounded by lush greenery.

"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."

Enjoy a serene beach experience with access to the ocean and a sailboat visible in the distance.

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

￥31,887 total

includes taxes & fees

Aug 27 - Aug 28

Stunning corridor with arches and columns, featuring traditional lighting fixtures and lush greenery.

"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! "

Relax in this spacious living area with a high ceiling, large windows offering views of the surrounding trees, and a comfortable seating arrangement.

"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. "

"Great stay. Would stay again. "

￥180,137 total

includes taxes & fees

Aug 18 - Aug 19

Enjoy sunbathing and relaxation on this popular beach with umbrellas and beach chairs.

"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. "

Walk along the beach on a paved path, bordered by grass and rocky shoreline, with the ocean stretching out to the horizon.

"Close to the shore and the heart of Old Saybrook. The house is very comfortable."

￥77,129 total

includes taxes & fees

Sep 8 - Sep 9

Surrounded by lush greenery, this cabin features a cozy porch with seating and a stone pathway leading to the entrance.

"My wife and I loved our weekend stay at this cabin!"

￥99,736 total

includes taxes & fees

Aug 31 - Sep 1

Stroll up to this charming colonial-style house, featuring a welcoming front porch with a bench and a beautiful garden.

"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!"

￥38,292 total

includes taxes & fees

Aug 11 - Aug 12

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Top Shelter Island Heights Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"Friendly staff, good restaurant "

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....."

Montauk Manor

10/10 Excellent

"Beautiful full service facility. We stayed in a friends unit which was lovely. The only complaint would be that when the pool is busy on summer weekends and the restaurant isn’t, it would be lovely if the waitresses could let patrons order drinks. It only happened once on the 3 night stay all of which had pool weather. Otherwise the manor is perfection. "

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:

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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?

Hamptons Retreat: 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. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island Heights?

With 47 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.

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Shelter Island Heights Vacation Rentals

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Vacation Rentals in Shelter Island Heights

Montauk Manor

The Surf Club

Montauk Oceanside Suites

Windward Shores Ocean Resort

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

Cliffside Resort Condominiums

Driftwood Resort

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

NORTHFORK COTTAGE with POOL & HOT TUB - thru Columbus day

Canoe Place Waterfront Residences

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

Hamptons Retreat

The Stern at Soundview · Beach+Ocean+Sunrise

MONTAUK MANOR-DELUXE STUDIO APARTMENT

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

Southampton cozy cottage by the beach

Charming Montauk Getaway centrally located

adorable ranch in beach community

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

Shoreline Oasis

Top Shelter Island Heights Hotel Reviews

Saybrook Point Resort & Marina

Greenporter Hotel

The Atlantic Hotel

Offshore Montauk

Marram

Best Western Niantic - New London/Mystic Area

Pier Blue Inn Old Saybrook - Essex

Sound View Greenport

Montauk Manor

Find out more about Shelter Island Heights

Frequently asked questions