Make no mistake, we love summer in the Hamptons — the themed lawn parties and gardens bursting with hydrangea, the dock and dines, and chic wineries. But if you’re looking for smaller crowds, pet-friendly beaches, Airbnbs at unbelievable rates, visit The Hamptons in the off-season. The accommodation options are just as elegant and worthy of a magazine cover as they are in July and August — from classic New England-style cottages with perfectly manicured gardens to sleek, modern beach houses with pools and hot tubs. Many feature designer-approved coastal decor, spacious backyards, and amenities such as Peloton bikes, fireplaces, and outdoor showers to make your stay worthy of a five-star hotel. Below, our favorite house rentals in the Hamptons to book on Airbnb, no matter the season.
Design-Forward East Hampton Estate
Country-house charm meets Hamptons chic at this elegant estate, tucked away on a private, manicured property. We love the crisp white interiors, rich wood accents, detailed ceilings, and spacious chef’s kitchen. Outside, lush gardens and a private pool set the scene for leisurely afternoons with family and friends.
Sun-Drenched Sag Harbor Home
Bike to Havens Beach, explore Sag Harbor’s shops, restaurants and bars, then return to this sun drenched, renovated home. Bright, airy, and deliciously spacious, we love the soothing, clean color palette with pops of color.
Sea Roost, Montauk
Built in the 1940s, this two-bedroom, two-bathroom original fisherman’s cottage is one of the last remaining at Montauk’s secluded Hither Hills Beach. We love the nautical curation and Old Man and the Sea vibe. There is also a separate artist studio on the property.
Stylish Sag Harbor Stay
This renovated Sag Harbor home is a five-minute walk from Havens Beach and 10 minutes from Main Street. The backyard features a heated pool and spa, lush gardens, and a large deck for outdoor dining. There’s also a home gym with a Peloton and Tonal for squeezing in a workout.
Elegant Southampton Retreat
Bright and spacious, this post-modern, Southampton retreat is truly a home away from home. The house features five bedrooms, 3.5 baths, living room with fireplace, outdoor hot tub and pool, and inside, a deep soaking tub. There is also a zoom-ready office setup for those working remotely. Pets (under 20 lbs) are welcome with pre-approval.
Historic Home With Private Waterfront, East Hampton
This 1958 mid-century home was designed by Kaneji Domoto, a student of Frank Lloyd Wright. Walls of glass showcase sweeping views of Three Mile Harbor, and the two-acre property extends to the shoreline with a private waterfront deck. Despite its secluded setting, East Hampton Village is just five minutes away.
Modern Beach House, Montauk
Walk or pedal (bicycles are provided) to town from this modern two-bedroom, two-bath, Montauk beach house. Recently refurbished, the interior is loaded with designer touches, while the outdoor fire pit is perfect in autumn.
Charming Sag Harbor Home
Just over a mile from Sag Harbor Village, this five-bedroom home sits on a quiet cul-de-sac away from the summer crowds. The light-filled interiors mix mid-century and antique furnishings, with plenty of space to settle in for a laid-back weekend out East.
Mid-Century Modern, East Hampton
Elegantly designed, this mid-century modern home offers clean lines, open spaces, and expansive windows. Set on two acres overlooking lush rolling lawns, the house features an open great room with high ceilings, exposed beams, a wall of glass, and a custom fireplace with a massive hearth. There is even a professional gym (with weight rack and Peloton), and a charcoal water filtration system that delivers Fiji-level purified drinking water out of every tap.
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