Holiday rentals with a hot tub in Bridgehampton

Home in Shelter Island

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.

7–14 Oct

Apartment in Southampton

Private w/Heated Pool Hot tub Fire Pit Coffee Bar

Relax in this cozy loft filled with amenities that will create lasting memories. Recently renovated so fresh and clean. Located on a wooded lot. Large fenced in landscaped yard with hammocks and firepit. Heated pool seasonal. We are just minutes from the beach. Spend time in our 6 person jacuzzi. 10 min to Southampton village. 15 min to Sag Harbor. Centrally located. Fresh farm (home of Tate’s Cookies) around the corner with fresh meats and produce. A tasty restaurant near by and a deli too.

10–17 Oct

Home in East Hampton

Waterfront Oasis + Pool/Spa & Private Beach

Waterfront in East Hampton! This perfectly renovated 5br | 3.5ba modern home with frontage on 2 bodies of water, offers stunning views year round. Relax by the saltwater heated pool & built-in spa or cozy up by the mid-century fireplace. WALK TO OUR PRIVATE BEACH & enjoy our 7 bikes, 4 paddle-boards & 3 kayaks, or take in the sunset over the water while you prepare dinner in the fully stocked chef's kitchen. Designer furniture promotes indoor-outdoor living w/refined simplicity. Registry#24-14

12–19 Dec

Home in East Hampton

Chic & Sun-Filled Modern Oasis, Heated Pool & Spa

Ideally situated between East Hampton & Sag Harbor, this stunning 5br & 4ba home is the perfect year-round escape. A gated entrance brings you inside a private 1 acre compound & up a 300ft long landscaped & lighted driveway. Greeted with sunny interiors, a modern floor plan, designer furniture & a 20x40ft sun-drenched heated saltwater pool, hot tub & roof deck, this beach house is perfect for large family gatherings and is an entertainer's dream with a fully stocked chef’s kitchen. #22-1,284

14–21 Apr

Home in East Hampton

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.

15–22 Oct

Cottage in Bridgehampton

Bridgehampton Cottage Close to Town, South of HWY

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 in 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. 30 night minimum in summer.

Guesthouse in Southampton

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

23–30 Sep

Home in Sag Harbor

Modern Home in Sag Harbor, NY

Set on high ground sits a sleek modern home, Published Richard Moger Modernist built the house for himself in the iconic Amagansett-style beach cottage of Charles Gwathmey. With over 2 acres of privacy is a perfect study in stylish modern design. The open plan, and floor to ceiling glass floods the home with light, showcasing the beautiful natural surroundings. Including a monthly tick and mosquitos professional treatments An updated velvety grey hues hot tub and jacuzzi

29 May – 5 Jun

Home in East Hampton

Springs Retreat Renovated Home, New Pool, Bay Walk

Welcome to the beautiful 3-bed, 2-bath Harbor House, located just a short walk from the picturesque Gardiners Bay. Enjoy open-concept living, fully equipped kitchen, comfy beds, and private patio with gas grill. Hot tub, garage, & washer/dryer included. Walk to harbor, rent kayaks/paddleboards, and 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 seaside adventure!

7–14 Feb