Shelter Island Heights Holiday Rentals: Short-Term Accommodations for Rent

Q: 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.

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Holiday Rentals in Shelter Island Heights

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

"Great hotel"

HK$4,311 total

includes taxes & fees

31 Jul - 1 Aug

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!"

HK$4,453 total

includes taxes & fees

11 Aug - 12 Aug

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

"great place to stay"

HK$3,187 total

includes taxes & fees

5 Aug - 6 Aug

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 "

HK$3,716 total

includes taxes & fees

7 Aug - 8 Aug

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

"Great property overall with beautiful grounds, a pool and access to the beach. Condos are spacious and equipped with bathroom and kitchen items. Ours had a patio with a great view of the water! We will definitely stay here again. "

HK$3,358 total

includes taxes & fees

31 Jul - 1 Aug

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!...

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."

HK$4,264 total

includes taxes & fees

31 Jul - 1 Aug

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

"Great place! Great communication with property owner!"

HK$4,733 total

includes taxes & fees

4 Aug - 5 Aug

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! "

HK$1,568 total

includes taxes & fees

31 Jul - 1 Aug

"Loved our stay and will be back"

Simple, functional room with a single bed and a window with curtains.

"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."

Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

"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!"

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. "

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."

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!"

HK$2,061 total

includes taxes & fees

31 Jul - 1 Aug

HK$9,605 total

includes taxes & fees

14 Aug - 15 Aug

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

"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "

HK$1,665 total

includes taxes & fees

6 Aug - 7 Aug

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

"Great space in a very convenient location. Will definitely look to stay here again in the future!"

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Top Shelter Island Heights Hotel Reviews

The Atlantic Hotel

10/10 Excellent

"Convenient "

Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which is in the back. Signage would have been nice. Second, the halls are like a maze. Once we figured it out - fine, but it took a while, especially since the parking is not close to the elevator to go up to the 3rd floor. The room itself was spacious and nice."

Sleep Inn & Suites Niantic

10/10 Excellent

"This hotel had a great mindset. All through the place there were posters promoting stress-free thoughts: breathe, meditate, stay calm, eat well, sleep well. Even the soap in the bathroom had a lotus shape. The bed was one of the most comfortable we have slept in. The free continental breakfast was fuller than many other hotels. I had never heard of the Sleep Inn brand before, but would definitely seek them out in the future."

The Pridwin Hotel

10/10 Excellent

"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely hotel. "

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 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.

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Shelter Island Heights Holiday Rentals

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Holiday Rentals in Shelter Island Heights

Montauk Manor

The Surf Club

Montauk Oceanside Suites

Windward Shores Ocean Resort

Cliffside Resort Condominiums

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

Driftwood Resort

Canoe Place Waterfront Residences

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Hamptons Retreat

The Stern at Soundview · Beach+Ocean+Sunrise

NORTHFORK COTTAGE with POOL & HOT TUB

Sag Harbor Suite by the Beach

Fairy Tale Guest Cottage in Magic Garden by Pool

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

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

Shoreline Oasis

Southampton cozy cottage by the beach

The Anchor at Soundview · Beach+Ocean+Sunrise

Charming Montauk Getaway centrally located

Top Shelter Island Heights Hotel Reviews

The Atlantic Hotel

Beachcomber Resort at Montauk

The Montauk Soundview

Offshore Montauk

Quality Inn Old Saybrook - Westbrook

Sleep Inn & Suites Niantic

The Pridwin Hotel

Kenny's Tipperary Inn

Best Western Niantic - New London/Mystic Area

Find out more about Shelter Island Heights

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Frequently asked questions