Holiday houses in Shelter Island

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Top-rated holiday rentals in Shelter Island

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

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Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 193 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

18–25 Nov

$1,963 NZD per night

Guest favourite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 310 reviews

Artists Sag Harbor Village Retreat

January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

1–8 Dec

$427 NZD per night

Guest favourite

Guesthouse in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

Kick back and relax in this serene, stylish, sparkling adorable cottage. Large, airy living room with vaulted ceiling, fan, AC and full open kitchen. Cozy bedroom with queen size bed and luscious European linens. Spacious, bright bathroom with roomy stall shower. Newly painted with charming wicker furniture and cafe bistro table, Apple TV, Sonos and wifi. Enjoy the peace and beauty of Shelter Island living. Long time residents, we are happy to share all the ins and outs of the island.

17–24 Dec

$744 NZD per night

Guest favourite

Guest suite in Greenport

4.92 out of 5 average rating, 276 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!

6–13 Jun

$547 NZD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - Apt #1

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).

5–12 Dec

$259 NZD per night

Guest favourite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

24–31 Oct

$1,323 NZD per night

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 220 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!

20–27 Aug

$997 NZD per night

Guest favourite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 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!

24–31 Aug

$736 NZD per night

Superhost

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay 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. Monday-Thursday stays February through June no cleaning fees!!!

2–9 Oct

$1,318 NZD per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 584 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

31 Aug – 7 Sep

$352 NZD per night

Guest favourite

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 227 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

20–27 Apr

$1,261 NZD per night

Superhost

Guesthouse in Sag Harbor

4.84 out of 5 average rating, 115 reviews

Sag Harbor Cottage in historic district

Charming studio cottage in the historic district of Sag Harbor. Walk to shops or restaurants downtown. Nearby beaches for swimming, kayaking or sailing. Great location to explore all of the Hamptons or get to know Sag Harbor with its unique charm and friendly atmosphere. We are the "un-Hamptons."

20–27 Oct

$279 NZD per night