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Holiday rentals in Shelter Island

Find and book unique accommodation on Airbnb

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Popular amenities for Shelter Island holiday rentals

Stay near Shelter Island's top sights

Mashomack Preserve20 locals recommend
Vine Street Café18 locals recommend
Marie Eiffel Market11 locals recommend
SALT Waterfront Bar & Grill17 locals recommend
IGA Shelter Island7 locals recommend
Commander Cody's Seafood9 locals recommend

Other great holiday rentals in Shelter Island

Superhost
Cabin in Shirley
4.87 out of 5 average rating, 156 reviews

A-Frame cabin with private beach & epic sunsets

FelixRating, 5 stars1 week ago
Amber‘s Haus ist einzigartig! Super Lage direkt am Meer mit spezieller Architektur. Bei der Ankunft sehr starker Rauchgeruch (wahrscheinlich durch das offene Kamin) im Haus bei stürmischem Wetter. War am nächsten Tag wieder weg. Eher kühl im Haus mit problemlosem Ansprechen der Heizung. Der Teppichboden ist gemütlich jedoch in die Jahre gekommen und hygienisch etwas schwierig. In der Küche gab es Anzeichen von etwas nachlässiger Reinigung. Die Betten waren gut und die Schlafzimmer sauber, auch die Badezimmer waren top! Alles in allem ein super Aufenthalt für 2 Nächte mit nur 5 Minuten Fahrzeit zum tollen Sandstrand. Wir würden wieder buchen!
Top guest favourite
Cottage in Guilford
4.99 out of 5 average rating, 137 reviews

"Red House on the Knoll" at Indian Cove

LauraRating, 5 stars2 days ago
This house is so cute! Very homey and clean throughout! Gail was flexible with our move in and was very kind and communicative. We had a terrific stay and would not hesitate to recommend it!
Top guest favourite
Home in North Fork
5 out of 5 average rating, 11 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

TimothyRating, 5 stars1 week ago
We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!
Guest favourite
Home in Hampton Bays
4.89 out of 5 average rating, 100 reviews

Hamptons Escape minutes from Beaches and Nightlife

EricaRating, 5 stars1 week ago
Our family spent a great weekend here. There was plenty of rooms for everyone to have their own, and everything was clean, cozy, and comfortable. The home was exactly as shown in the pictures and everything we could have needed was there. The hot tub was lovely both nights, and the pool area looks pretty though was not yet opened for the season. This is a perfect spot to bring your family, to relax, and enjoy all that the Hamptons, and Hampton Bays has to offer. We hope to return soon!
Guest favourite
Cabin in Rocky Point
4.89 out of 5 average rating, 486 reviews

Great little place just for a couple

MeganRating, 5 stars6 days ago
A wonderful spot and wonderful host. Everything was cheery and thoughtfully done. I knocked off a star for the price mostly because I wasn't anticipating how expensive it is to get around by Uber in the area, and to find an accessible grocery store - otherwise necessary to have a car. Ended up ordering UberEats... my mom was at another Airbnb down the road and the difference in how we were treated as guests was astronomical. Marina did not charge me for having my little dog, there was a little firewood for us to use, fresh coffee and tea, and all the amenities! Marina was also very responsive and kind, and left a very helpful note about whether the beach is public or not. 100% recommend. In contrast, my mom felt badly treated by the host, the place was poorly kept and she felt it was way overpriced in comparison to mine (Marina's). Good thing she was able to come here during the day, and we spent most of our time here, in the yard or the short walk to the beach.
Guest favourite
Guest house in Shelter Island
4.96 out of 5 average rating, 27 reviews

Sleek and Chic cottage/Pool House

YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favourite
Home in North Fork
4.92 out of 5 average rating, 12 reviews

Private Beach access along the Wine Trail

RaeganRating, 5 stars1 month ago
I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Quick stats about holiday rentals in Shelter Island

  • Total rentals

    150 properties

  • Nightly prices starting at

    £8 before taxes and fees

  • Total number of reviews

    3.1K reviews

  • Family-friendly rentals

    110 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Destinations to explore