Holiday rentals in Shelter Island Heights

4.91 out of 5 average rating, 107 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

4.92 out of 5 average rating, 140 reviews

Apartment in North Fork

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

4.96 out of 5 average rating, 164 reviews

Shelter island retreat

Two bedroom on the top floor of a house on Shelter Island on secluded one-acre. fire pit, wood-burning fireplace, layered decks, stainless steel kitchen, five minutes to beach. close to the south ferry .outdoor sauna and hot tub. Own entrance very private. owner lives on property as well in very separate space. 19W-0009 Own entrance very private. owner lives on premise as well in very separate space.has cat that lives in studio with owner 19W-0009 Long term rental also Available

Guest suite in North Fork

4.91 out of 5 average rating, 315 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

4.94 out of 5 average rating, 187 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

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

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

4.97 out of 5 average rating, 260 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Guest house in Shelter Island

5 out of 5 average rating, 64 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

4.9 out of 5 average rating, 214 reviews

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

4.96 out of 5 average rating, 104 reviews

Flat in North Fork

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

Superhost

4.9 out of 5 average rating, 116 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Flat in Shelter Island Heights

4.91 out of 5 average rating, 247 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Shelter Island Heights holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Shelter Island Heights

5 out of 5 average rating, 13 reviews

Waterfront Treehouse with Pool as seen on HBO

Susan BRating, 5 stars3 weeks ago

This very unique home is in the most beautiful spot on Shelter Island. Paradise. An incredible view of the creek on one side, a gorgeous pool and garden on the other. The house is so pretty, spacious and well-equipped. Hosts are extremely responsive and accommodating. I would definitely go back.

5 out of 5 average rating, 5 reviews

Designer Renovated Farmhouse with Pool

FrancisRating, 5 stars1 month ago

We really needed the solitude and my daughter and I had a fantastic rest. What a great place to hibernate in the winter! Great comfortable beds, well stocked kitchen In a beautiful space. It is a bird sanctuary with nice walks and brilliant cycling.

5 out of 5 average rating, 3 reviews

New vacation house on the island(new pool)

JamesRating, 5 stars9 months ago

Iwona was a terrific host. The home is immaculately maintained, with high ceilings and large windows looking over beautiful green space. It is a calming environment, both indoors and out. The location is convenient to the town center, a nature preserve, beaches, restaurants, and the north and south ferries. Based on our experience, we recommend highly!

4.99 out of 5 average rating, 93 reviews

Greenport Village Rental

DavidRating, 5 stars9 months ago

What a perfect stay for our family of 4 (kids are 5 and 1). Michael was a very proactive host and told us everything we needed to know ahead of time. Worked with us to get us in as early as possible on check-in day. Very responsive and helpful. How was so awesome and a straight shot down to the beach. 5 minute walk into town. Can’t wait to be back soon

Guest house in Shelter Island

4.89 out of 5 average rating, 9 reviews

Stylish Studio Suite on Shelter Island

AnnaRating, 5 stars10 months ago

Kate’s place was perfect—down a quiet and private road but close to everything Shelter Island has to offer. The apartment was cozy and comfortable with all the necessities. Kate was very responsive when needed but you also have privacy. Lovely stay—I hope to come again!

Flat in Shelter Island

5 out of 5 average rating, 15 reviews

Modern Waterview Apartment in Silver Beach

MarkRating, 5 stars3 weeks ago

We really enjoyed our stay at Ena and Robs well appointed quiet apartment on shelter Island. It was in a great location close to beaches and in a perfect spot to bike around the island. Everything in the apartment was of a high quality, spotlessly clean including the comfortable bed and the linens, the kitchen was well equipped, the shower very nice and there was a lovely little balcony to sit and have your coffee in the morning. The host were very friendly and open. We would definitely go back!

5 out of 5 average rating, 4 reviews

Delightful Cape House in Greenport

CameronRating, 5 stars3 weeks ago

Kyra was an amazing host and we loved staying in her home! She has clearly done so much work to make it feel comfortable for groups, cozy for relaxing, and worth the listed price. Her attention to detail was very clear - tons and tons of soft towels, beach towels, great shampoo and toiletries, ample cookware that was very high quality, spices for cooking, and lots of pool toys. We got lucky enough to go at a time when a local farm had a weekend of family events. We ate fresh strawberries, had local beer, and toured local antique shops. This was the best Airbnb experience we’ve had and would definitely return!