Holiday rentals 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.

Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor 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

€ 710 per night
Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 189 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.

1–8 Dec

€ 1,030 per night
Guest favourite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 308 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.

15–22 Nov

€ 234 per night

Popular amenities for Shelter Island holiday rentals

Stay near Shelter Island's top sights

SALT Waterfront Bar & Grill34 locals recommend
Mashomack Preserve70 locals recommend
Ram's Head Inn19 locals recommend
Marie Eiffel Market41 locals recommend
South Ferry Inc.6 locals recommend
The Islander10 locals recommend

Other great holiday rentals in Shelter Island

Guest favourite

Guest suite in Shelter Island

4.89 out of 5 average rating, 28 reviews

Private two-bedroom stay on Shelter Island

5–12 Jun

€ 334 per night
Guest favourite

Guest house in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

12–19 Jun

€ 403 per night
Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

6–13 Feb

€ 617 per night
Guest favourite

Guest house in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

27 Nov – 4 Dec

€ 408 per night
Guest favourite

Home in Shelter Island

4.92 out of 5 average rating, 52 reviews

Beautiful beach home with pool & water views!

25 Jan – 1 Feb

€ 625 per night
Guest favourite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

25 Oct – 1 Nov

€ 672 per night
Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

1–8 May

€ 759 per night
Guest favourite

Cottage in Shelter Island

4.96 out of 5 average rating, 90 reviews

3 Bedroom Cottage Gem

19–26 Jun

€ 700 per night
Guest favourite

Cottage in Shelter Island

4.88 out of 5 average rating, 16 reviews

Waterfront Getaway on Shelter Island

19–26 Oct

€ 788 per night
Guest favourite

Home in Shelter Island

5.0 out of 5 average rating, 16 reviews

Family Friendly Oasis Steps to Water - Heated Pool

6–13 Oct

€ 1,113 per night
Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 76 reviews

Modern, spacious SI home with pool

11–18 Feb

€ 882 per night
Guest favourite

Cottage in Sag Harbor

5.0 out of 5 average rating, 27 reviews

Luxury Gem At The Heart of Sag Harbor Village

5–12 Jun

€ 723 per night

Quick stats about holiday rentals in Shelter Island

Total rentals

140 properties

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

Destinations to explore