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.

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Superhost

Home

5 out of 5 average rating, 4 reviews

Charming- In village/bike2beach

Cottage escape spans 1/2 acre; blocks from town & bike ride to Coopers. Gourmet kitchen, livingroom/fireplace, queen-size bedroom downstairs, with laundry and bath. Upstairs: master and guest bedrooms. Outdoors, lush gardens, pool, pergola, cabana, which offer an enchanting sanctuary for relaxation & alfresco living. Whether strolling among fragrant blooms, lounging by the pool, or enjoying outdoor bbq. Timeless charm & contemporary luxury! Month rental -Only avail for aug. + Security deposit

Guest favourite

Flat

4.96 out of 5 average rating, 27 reviews

Beautiful Sunny one bedroom apt in SH. NY.

Enjoy a stylish experience at this centrally-located place. This stunningly-beautiful sunny apartment is located in the heart of Southampton New York, where the sea and the earth elements create the most peaceful setting. The apartment has a private entrance and private bathroom, is located at a short walking distance to Main Street, library, grocery stores, restaurants, shopping stores and pharmacies. PLEASE NOTE: PETS ARE NOT ALLOWED. QUITE TIME 10 PM -9AM

Superhost

Home

5 out of 5 average rating, 4 reviews

Summer Main Home plus cottage close to Main Street

Come relax and enjoy! Beautifully updated Main home with separate cottage. Perfect for in-laws and guests. Each home has its own kitchen, living space, washer/dryer, and outdoor seating. Main house: 4 Br, 3 ba Cottage: 2 Br, 1 ba Outdoor shower for an after beach rinse, 2 patios, pergola, hammock, bbq. A two person kayak available for use; beach passes included. Games, internet, tv... Walk to coffee shops, restaurants, worship, and marina. Bike to beach.

Guest favourite

Houseboat

5 out of 5 average rating, 10 reviews

Peconic River Boatel

Perfectly updated nautical houseboat situated on the scenic Peconic River. Featuring two picturesque bedrooms, a full service eat-in kitchen and a living room with panoramic river view. Enjoy your morning coffee on the outside deck while taking in the sunrise. This historic waterfront town was named to Forbes Advisor’s “Best Places to Travel in 2023” — one of just 11 U.S. destinations on this year’s list. A must see for adventurers and families alike!

Guest favourite

Home

5 out of 5 average rating, 6 reviews

Hilltop Bright Home w/New Pool Summer 2024

Home is professionally managed by Montauk Rental Management Group. Your family will be close to everything when you stay at this centrally-located Montauk home. Short drive to Town and Beaches. This home was recently painted and updated, it's clean, bright and the perfect family rental! -4 bedrooms -3 bathrooms -Spacious deck with water views -Outdoor dining & seating -Grill -Peaceful, quiet location perched on a hill Rental Registry 23-780

Guest favourite

Home

5 out of 5 average rating, 39 reviews

5-Star Listing: Hamptons Oasis, Easy from NYC

Welcome to our coastal retreat. Minutes away from Westhampton Beach and a super-easy commute from NYC. Perfect for families or a group of close friends to get away from it all. A bright, spacious, recently renovated home with light-filled rooms, new floors, coastal decor. Ultrafast Wifi, Alexas, and a new kitchen with the latest appliances. Beautifully landscaped gardens, heated pool, 6-person salt water hot tub (in winter or summer)!

Superhost

Home

4.9 out of 5 average rating, 115 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. Cleaning fees for winter stays are 0$.

Guest favourite

Home

4.9 out of 5 average rating, 42 reviews

Montauk Family Gem: HotTub, Pro Kitchen, Fireplace

Escape to your perfect Montauk getaway! Nestled on a secluded, beautifully landscaped lot at the end of a quiet dead-end street, this recently renovated 4-bedroom, 3.5-bathroom beach house offers the ultimate combination of luxury, comfort, and privacy—just one mile from both Montauk town and the famous Ditch Plain beaches. We are also pet friendly!

Guest favourite

Home

4.98 out of 5 average rating, 173 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Guest favourite

Home

5 out of 5 average rating, 25 reviews

Convenient 2 Bedroom Hampton’s Getaway

Your family will be close to everything when you stay at this centrally-located beach house . Close to beaches, restaurants and shopping. Biking and walking distance to Town and Ocean. You can also take advantage of our close proximity to the North Fork and the wineries. Montauk is about 35 miles east.