8 East End Getaways for the Winter Season

Photo: Grant Monahan
Photo: Grant Monahan

We know what you’re thinking. “Montauk? In the winter? People do that?” Truthfully… not really. But if you’re looking for a place to gather family + friends together for the holiday season, cozy up and watch 57 Christmas movies in a row for an entire wintry weekend, there’s probably no place better to bunker down inside for a wintry week than on the East End.

From sprawling kitchens (perfect for the cooking of wild game) to blazing fireplaces, these eight Airbnbs will have you reimagining the traditional Christmas vacation experience for days. At the very least you can experience Montauk in the offseason, when the number of tourists — and prices — drop with the temperature.

1. Oasis by the Beach

If it’s one of those famous warm New York winter days, you can take advantage of the beach. The owners refer to their place — which can accommodate up to six guests — as “a little bit of Malibu in Montauk.” And the California-style touches stand up to the claim. (Hey, if you’re going to be stuck indoors, why not be stuck somewhere beautifully decorated?) The first floor houses a decked-out kitchen, living family and dining rooms and two bedrooms. Upstairs, the private master suite has a king bed, ensuite bathroom and a balcony.

More details + booking: Here

WinterWonderland56.48 PM

Photo: Airbnb

2. Beautiful Beachside Home

Located in the chic, exclusive Bluffs area of Montauk, this three-story house sits on two acres in a gated community. There’s room for eight guests to lounge in the sun-drenched living room, feast at the large dining room table or hang by the fireplace. The rustic place also offers direct access to a private beach and a gym. Oh, and a local house manager is available for onsite requests. Now that’s a vacation.

More details + booking: Here

3. Modern Montauk Retreat

Clean. Modern. Quiet. If this sounds like your idea of relaxing, check out this 1950’s renovated ranch home. The bedrooms include a master with a king bed and water views, and another room with a double bed. Situated close to town, it’s easy to get around. Alternatively, a flat-screen TV can keep homebodies occupied.

More details + booking: Here

WinterWonderland54.51 PM

Photo: Airbnb

4. Chic Chalet

This spot is close to both the water and the local watering holes. A cozy option for couples and families with kids, this 4-bedroom getaway is sleek, modern and airy. There’s an indoor fireplace, a huge tub for soaking and a lovely, large farmhouse dining table. Two living room areas means there is plenty of room for eight people to spread out.

More details + booking: Here

5. Waterfront Cottage

Perched above Fort Pond, this bohemian cottage includes two bedrooms, sweeping windows with waterfront views and an outdoor fire pit. Decorated with “a mix of bought and found objects” the relaxed, spacious home offers a stocked kitchen, two spacious bathrooms with marble floors and wi-fi throughout.

More details + booking: Here

WinterWonderland57.31 PM

Photo: Airbnb

 6. Surfside Stunner

Thought “surfer chic” was only for the summer time crew? This seven (!) bedroom spot will make you think again. With three living areas that include decks overlooking the Atlantic Ocean and Shadmoor State Park, this sprawling house has been professionally decorated with beach-inspired touches. The 5-bedroom 4.5-bathroom estate is walking distance from town. Oh, and there’s a hot tub.

More details + booking: Here

7. The Surf Haus

This fully renovated, 4-bedroom beach house boasts a sprawling master suite as well as a separate upstairs wing which contains two more bedrooms and a shared bath. Downstairs, you’ll find the beautifully-decorated den with vaulted ceilings and an expansive deck with sweeping water views of Fort Pond Bay, the ocean and the Long Island Sound. There’s room for eight, so bring friends and gather ‘round the fireplace.

More details + booking: Here

WinterWonderland55.57 PM

Photo: Airbnb

8. Montauk Tower House

Dubbed “The Perfect Montauk Getaway” by its hosts, this bright, colorful and opulent abode has windows and skylights abound. There are three bedroom suites, each with queen beds and private baths on both levels of the house. A very short drive to downtown Montauk, it’s easy to dine out — but, for master chefs, the kitchen is fully equipped with everything you’d need to facilitate gourmet meals. And then you can enjoy those meals around the 8-person South American Bubinga hardwood table.

More details + booking: Here

To see more of the East End during its beautiful, low volume months, check out Grant Monahan’s “The Offseason” feature.