Shelter Island Holiday Homes
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Featured Holiday Homes in Shelter Island

3-bedroom Montauk Coastal Getaway

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Stunning Waterfront Home with Private Beach!

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Escape to Sag Harbor
Holiday Accommodation Shelter Island
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Shelter Island are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Shelter Island itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Shelter Island holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Shelter Island, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Shelter Island with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Shelter Island Holiday Homes essential information
Accommodation | 2043 Holiday Homes |
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Popular accommodation | 3-bedroom Montauk Coastal Getaway, Charming Two-Story Retreat in Southampton Village walk to town, beach and train., Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️, Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen, Stunning Waterfront Home with Private Beach!, Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach, Driftwood Cottage by RoveTravel| 3BR Quiet Cottage, Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor , Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton, Escape to Sag Harbor, The Cooper-Burke House, Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10 |
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Montauk Yacht Club
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