Holiday rentals in Shelter Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Shelter Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Remsenburg-Speonk

5 out of 5 average rating, 40 reviews

5-Star Listing: Hamptons Oasis, Easy from NYC

AldaRating, 5 stars3 months ago

This was our second stay for a relaxing New Years with our dear friends. Perfect distance and location for us - Eric’s home is like going to your home…but better. For us the kitchen, dining room and two family/living rooms make this perfect for our gathering. Well equipped and beautiful kitchen gives us all a chance to cook, and the dining room is perfect for all of us. The house is as pictured- pristine and beautiful. Highly recommend and would really like to come back in the Summer to enjoy the beautiful grounds and pool!

Superhost

Home in North Fork

4.67 out of 5 average rating, 12 reviews

Queen Vic Beach House: 5 Mins to Vineyards & Farms

AdamRating, 5 stars1 month ago

After an initial snafu with my booking through the app, Debbie sprung to action, contacted me, and upgraded us to this house, which was even nicer and closer to the ocean than the house I originally wanted to book. I thought she handled what could have been a very upsetting situation extremely well and overcompensated for us, if anything. Place and location were wonderful. Definitely recommend.

Holiday rentals for every style

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Unique stays

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Popular amenities for Shelter Island holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Shelter Island's top sights

Mashomack Preserve70 locals recommend

Vine Street Café61 locals recommend

Marie Eiffel Market41 locals recommend

SALT Waterfront Bar & Grill34 locals recommend

IGA Shelter Island28 locals recommend

Commander Cody's Seafood22 locals recommend

Other great holiday rentals in Shelter Island

Superhost

Cabin in Shirley

4.86 out of 5 average rating, 147 reviews

A-Frame cabin with private beach & epic sunsets

ScottRating, 5 stars3 weeks ago

A great stay. We will be back. :)

Superhost

Home in West Haven

4.63 out of 5 average rating, 35 reviews

Coastal Cottage.

YuchengRating, 5 stars3 months ago

Pretty good! We enjoyed our holiday in this beautiful and peaceful house.

Guest favourite

Home in Montauk

4.85 out of 5 average rating, 52 reviews

Stunning Serene and Secluded Ocean Retreat!

HannahRating, 5 stars5 months ago

We stayed at Missy’s place for a family get away. Location was so peaceful and the house was exactly as described! We can’t wait to go back!!

Top guest favourite

Cottage in Guilford

4.99 out of 5 average rating, 133 reviews

"Red House on the Knoll" at Indian Cove

FranRating, 5 stars1 day ago

Best Air bnb we've stayed at so far. House is spacious, beautifully decorated and immaculately clean. we felt very welcomed with snacks and a stocked fridge. The layout was ideal for our two families to each have our own wing. We will try to stay here anytime we are in CT.

Guest favourite

Cabin in Rocky Point

4.89 out of 5 average rating, 478 reviews

Great little place just for a couple

AmandaRating, 5 stars1 week ago

Marina’s place was exactly as described and just what we needed to be able to stay somewhere with our pups and attend our friend’s wedding. It was very clean and there was a wide range of amenities available! The neighborhood was very quiet and the little outdoor area with fire pit is so cute!

Guest favourite

Home in Woodmont

4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 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!

Top guest favourite

Home in Old Saybrook

5 out of 5 average rating, 49 reviews

Great Hammcock Getaway, Nearby beaches, Hot tub

DavidRating, 5 stars2 weeks ago

What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.

Superhost