Holiday rentals in Shelter Island
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Top-rated holiday rentals in Shelter Island
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Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.
26 Mar – 2 Apr
Home in Shelter Island
4.97 out of 5 average rating, 189 reviewsHuge 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.
1–8 Dec
Guest suite in Sag Harbor
4.88 out of 5 average rating, 308 reviewsArtists 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.
15–22 Nov
Holiday rentals for every style
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Popular amenities for Shelter Island holiday rentals
Other great holiday rentals in Shelter Island
Guest suite in Shelter Island
4.89 out of 5 average rating, 28 reviewsPrivate two-bedroom stay on Shelter Island
5–12 Jun
Guest house in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
12–19 Jun
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
6–13 Feb
Guest house in Shelter Island
4.95 out of 5 average rating, 22 reviewsLovely Island Cottage
27 Nov – 4 Dec
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
25 Jan – 1 Feb
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
25 Oct – 1 Nov
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
1–8 May
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
19–26 Jun
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
19–26 Oct
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
6–13 Oct
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
11–18 Feb
Cottage in Sag Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Gem At The Heart of Sag Harbor Village
5–12 Jun
Quick stats about holiday rentals in Shelter Island
Total rentals | 140 properties |
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Rentals with a pool | 50 properties have a pool |
Pet-friendly rentals | 50 properties allow pets |
Family-friendly rentals | 100 properties are a good fit for families |
Total number of reviews | 3K reviews |
Nightly prices starting at | € 111 before taxes and fees |
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