Shelter Island Holiday Rentals from €174: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Shelter Island has to offer?

Hamptons Retreat : This holiday home rental outside of Shelter Island 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

"Great hotel"

includes taxes & fees

1 Sept - 2 Sept

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

includes taxes & fees

3 Sept - 4 Sept

"great place to stay"

includes taxes & fees

26 Aug - 27 Aug

Ocean View 2BD Corner King and Queen | Living area

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

includes taxes & fees

2 Sept - 3 Sept

"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!...

"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. "

includes taxes & fees

4 Aug - 5 Aug

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

includes taxes & fees

3 Sept - 4 Sept

"Great place! Great communication with property owner!"

includes taxes & fees

4 Aug - 5 Aug

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

"Loved our stay and will be back"

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

includes taxes & fees

27 Aug - 28 Aug

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

"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. "

"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. "

includes taxes & fees

14 Aug - 15 Aug

"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!"

includes taxes & fees

4 Aug - 5 Aug

"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. "

includes taxes & fees

19 Aug - 20 Aug

"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!"

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Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"We arrived late at night and the staff were so very friendly and accommodating. We had a small issue in our room and the staff responded immediately and so graciously to resolve it. We have stayed here before and have always enjoyed our stay. "

Find out more about Shelter Island

Everything you need to know about Shelter Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as €174 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Shelter Island has to offer?

Hamptons Retreat: This holiday home rental outside of Shelter Island 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?

Choose from 84 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.

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Holiday Rentals in Shelter Island

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Holiday Rentals in Shelter Island

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

Sag Harbor Suite by the Beach

Canoe Place Waterfront Residences

Hamptons Retreat

NORTHFORK COTTAGE with POOL & HOT TUB

The Stern at Soundview · Beach+Ocean+Sunrise

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

Charming Montauk Getaway centrally located

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

Southampton cozy cottage by the beach

Shoreline Oasis

The Anchor at Soundview · Beach+Ocean+Sunrise

Fairy Tale Guest Cottage in Magic Garden by Pool

Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Marram

The Bentley Hotel Southampton

Beachcomber Resort at Montauk

Hyatt Place Long Island East End

Sound View Greenport

Montauk Blue Hotel

Offshore Montauk

Saybrook Point Resort & Marina

Find out more about Shelter Island

Frequently asked questions