Holiday rentals in The Hamptons

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Luxe NEW Beach Cottage-Steps to Water-Firepit

Kick back and relax in this calm, stylish beach cottage with NEW Kitchen and NEW bathroom (completed April 2026) in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in May-Sept. Beach chairs, umbrella and smiles!

Sunlit cozy cottage by the bay.

Kick back and relax in this calm, stylish space.This serene and light-filled cottage in the heart of historic Springs has been thoughtfully restored using sustainable materials and modern amenities. Just a short walk from Maidstone Beach and beloved local spots like the Springs Tavern and the charming S and S Corner coffee shop, this peaceful retreat blends minimalist elegance with high-end comfort.The cottage is stocked with organic linens and luxurious down duvets for a restful nights.

Designer home in Sag Harbor : 5BR walk to beach

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

4 BR/3BA Quiet Pool Home

We welcome you to our family home, up to 5 guests, pets are welcome with additional pet fee. Nice new pool and surrounding deck with outdoor sitting area, chairs, umbrella, and charcoal grill. 1 gbps internet for movies streaming on disney plus, prime video, or for your work. 5-8 minutes to town and the beaches. Plenty of nice restaurants and great local shopping. We don't allow other guests on property that is not mentioned in advance. No gatherings and no parties. Thank You.

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Private, calming, and stylish Hamptons retreat—the ultimate escape from the city. Enjoy an inviting swimming pool from the surrounding hammock, lounge chairs, and swing. The best of indoor-outdoor living is steps away on the wraparound deck featuring an outdoor kitchenette with BBQ, a large outdoor dining table with seating for 12, and an outdoor gas-powered fireplace. All this against the backdrop of 4 acres of private forest greenery.

Charming Bungalow on the Bay

This newly remodeled 1960’s bungalow is the perfect getaway for couples and families alike. Located right on Gardiner’s Bay, there’s a gorgeous view of the water from the large windows and front porch. From the front steps you can follow the 300 yard path to your own private beach where you can wade, swim, snorkel, paddleboard, or just enjoy the amazing view and salt air. (East Hampton Rental Registry Certificate Number: 24-234)

Steps to Train, Dining & Beach US Open Golf

SOUTHAMPTON HOUSE NEW YORK charming cottage escape with a separate guest house, perfect for 7 guests. Relax in our private courtyard, complete with an outdoor kitchen with green egg, and fireplace for cozy nights under the stars. Just steps from the LIRR and walkable to downtown’s boutiques, restaurants, and attractions, our location is unbeatable. We’re just 2 miles from Coopers Beach.

Dockside 2BR - Prime Location on the Marina Unit B

Morning coffee with boats bobbing out front, dinner next door at Fish House, and lazy walks up to Gosman’s for fudge and harbor views — this is the best of dockside living, Montauk style. Tucked in Westlake Marina, at this fresh, sun-filled 2-bedroom, enjoy comfy beds, a fully equipped kitchen, and easy access to boat charters, seafood, and sunsets.

Best View + Putting Green + Private Beach

Perched high atop Shinnecock Hills, our home boasts panoramic bay and ocean views unlike any other in the Hamptons! Tranquil, sanctuary like setting with manicured landscaping, mature privacy trees, waterfalls, like your own arboretum! Private beach, local favorite restaurants and hang outs are within walking distance!