Holiday rentals with a hot tub in Napeague

Secluded Luxury: New Gunite Pool, Walk to Bay

Welcome to the beautiful 5-bed, 3-bath Harbor House, located just a short walk from Gardiners Bay beaches. Enjoy open-concept living, fully equipped kitchen, comfy beds, gunite pool, private patio with gas grill & outdoor dining, hot tub, & fully fenced backyard. Walk/bike to harbor, rent kayaks, use our paddleboards, or explore nearby restaurants and shops. Whether you’re looking for a romantic getaway for 2 or a family vacation, our home is the perfect retreat for your next Hamptons adventure!

New Private EH Home Pool Jacuzzi Sauna Game Gym

Nestled in a quite neighborhood, this 5300 sq ft 7-BR, 6-BA designer smart home offers 2 living rooms, fast wifi, large kitchen island w/ 8 person dining table, gym and sauna, game room, pool and Jacuzzi, covered outdoor living and dining room, front porch with swings, and steam spa. The elegant interior meets an open outdoor fenced-in oasis, making it perfect for getaways. This home has plush amenities to try and meet all your needs from high end kitchen appliances to bath and body essentials.

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Ranked #1 AirBNB. Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Beachside Escape from NYC

Topping Rose House has been standing on the same intersection of Montauk Highway in Bridgehampton since 1843. The hotel was renovated and reopened in 2012 and is now the preeminent place to feel like a Hamptonite. In the summer, relax by the pool or bike to the Atlantic. In the winter, enjoy the stunning landscape of the villages of the Northeast. The hotel has 22 rooms, and is only listing on AirBnB for a limited time. The specific room type is assigned on the day of arrival.

Montauk Village

Remarkable newly built home in Montauk, Winter Sunset View, Walk to Beaches and Restaurants. You will have a stylish experience at one of the most sought after seaside destinations. 3 bedroom, 2 full bathroom and 2 half baths. 9 minute walk to village beaches, restaurants/bars, and shopping In the mood to stay in? Enjoy the hot tub and fire pit. Watch the beautiful Montauk Sunsets "winter is best" from the deck! Central air, internet and wifi

Private Oasis W/Stunning Vinyard and Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.