2 Bedroom Houses for Rent in Amagansett, NY

RR#: R-26-0005 Set on a lush half-acre in the heart of Sag Harbor Village, this inviting post-and-beam home with a swimming pool offers a peaceful escape less than one mile from Main Street's boutiques, dining, and village amenities. A private gate in the backyard opens directly to Mashashimuet Park, where you'll find tennis and basketball courts, a running track, nature trails, playgrounds, and open green space. Inside, warm, soothing tones pair with abundant natural light and exposed wood beams to create a relaxed, welcoming atmosphere. The second level features

Charming cottage located just minutes to down town Sag Harbor Village in North Haven. Furnished and ready for a perfect weekend retreat.

Rental Registry#: 26-515 Once the home of Irving Berlin's musical partner and currently belonging to the musician Rufus Wainwright, this beach cottage exudes the aura of creativity a peaceful retreat by the ocean inspires. Sitting privately in the Hither Hills area of Montauk, this 2 bedroom/1 bath original Leisurama house has a decidedly modern and chic 50's sensibility. There are lovely grounds, fully fenced, with an oversized deck, a secreted outdoor shower, a new sauna and outdoor hot tub. Above the separate garage is a large studio and full bath, complete with Rufus'

Property Status: Active Discover this unique 2-bedroom, 2-bathroom duplex set within a historic 1800s home. Featuring a loft-like layout with open living space and timeless character, this home offers the perfect blend of charm and comfort. Ideally located in the heart of Greenport Village, enjoy walking distance to local shops, restaurants, beaches, and renowned North Fork vineyards. Convenient access to the LIRR and Orient Point Ferry makes travel a breeze. A perfect opportunity for a year-round residence in one of the North Fork's most desirable locations. Office Phone:

Property Status: Active Beautifully Renovated Greenport Village Farmhouse with Bay Beaches Nearby. Summer 2026 - Memorial Day to Labor Day $45,000; Memorial Day thru June $12,000; July $16,000; August to Labor Day $20,000. Office Phone: (631) 553-5255 Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Property Status: Active Soak up the perfect Hamptons summer in Sag Harbor w/ your very own private spa experience. The sunny pool house featuring a gunite pool, yoga deck and sauna will melt your cares away upon your arrival, after a day at the beach or after a day strolling through downtown Sag Harbor. The primary bedroom features vaulted ceilings, a skylight, a ceiling fan a king size bed and in wall speakers. The primary bathroom features a large bath tub and an enclosed steam shower. Fully fenced backyard for a worry-free time. Easy access to Cromer's Market. Less than

Property Status: Active Southampton Village Gem in mint condition with beautiful gardens, mature landscaping and Gunite pool. This home and property are turn key. It offers 1025 square feet of entertaining space between the main residence and the fabulous pool house. The home and property are wonderfully appointed and located on a quiet lane in Southampton Village just moments from the shops and ocean beaches. Available $5,000 monthly - February, March or April 2026 $10,000 May 1st to 31, 2026 $25,000 June 1st to 30, 2026 $40,000 July 1st to 31, 2026 $45,000 August 1 to Se

Property Status: Active Discover the charm of this beautifully maintained 2-bedroom, 1-bath home located in the heart of Greenport, NY. Perfect for year-round living, this cozy residence offers comfort, style, and the peaceful charm of the North Fork. Nestled on a quiet street, this home is just minutes from Greenport Village's boutique shops, restaurants, beaches, and the LIRR station. Enjoy everything the North Fork has to offer - from local vineyards to waterfront sunsets - all within easy reach. If you're looking for a charming and comfortable home close to the village

Property Status: Active This Completely Renovated One-Of-A-Kind Historic Religious Structure was built in 1879. Stylish And Close To Everything In Greenport. Soaring Cathedral Ceilings, Mesmerizing European Stained Glass Windows, Brand New Kitchen And Full Bath. Located In The Heart Of The Much Coveted Greenport Village. Moments Away From Top Restaurants, Trendy Stores, A Sugar Sand Local Beach, The LIRR Station, And The Jitney Bus Stop. This Is A Unique Opportunity To Stay In A Piece Of History Alongside Modern Amenities To Make Your Stay Simply Unforgettable! Full month

RP#260038 Escape to the tranquility of waterfront living with this 2 bedroom 2 bathroom cottage - perfect for those who crave stunning sunsets, serene waters and nature. Nestled right on the water this cozy haven offers endless relaxation and summer entertainment, whether you are hosting friends or enjoying a quiet retreat. Amazing sunsets - Enjoy breathtaking views every evening from your outdoor covered porch or private patio where you can dine al fresco while the sun sets. Boating -Step outside to your own private dock where you can kayak, boat or paddle right of

Enjoy the perfect location for convenience and coastal living. This charming 2 bedroom and 1.5 half bath home just a few blocks from Main Street's shopping, restaurants and the ocean beaches. Step inside and be greeted by the open plan with wood-burning fireplace, multiple oversized glass doors open to central deck and garden allow for one story living at its best. Designer owner touches throughout create a warm and inviting atmosphere. The recently renovated kitchen and fresh furnishings will make for a great summer experience on one of the most desirable streets in Sout

Property Status: Active Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000, July $8000, November $3500, December $3500 Southold Town Rental Permit #0374, Additional information: Appearance: Excellent Office Phone: (631) 335-1878 Cop

Property Status: Active Located only 1.3 miles from the iconic Shinnecock Hills Golf Club, this adorable and stylish 2-bedroom, 1-bathroom home is the ideal rental for the 2026 Shinnecock Open-or simply a relaxing Southampton escape. The interior features a newly renovated kitchen with stainless steel appliances, a comfortable living room, and both a family and sitting room for added space and flexibility. Thoughtfully furnished with charm and comfort in mind, it's a perfect home base for summer living. Step out back to enjoy a covered porch overlooking a beautifully lands

Property Status: Active Delightful and welcoming two-bedroom, one-bath home available for summer rental and during the U.S. Open, ideally located just 0.8 miles from Shinnecock Hills Golf Club. This warm and inviting property features a stunning, newly renovated kitchen with modern finishes, all appliances, and a convenient wine refrigerator, along with a tastefully updated, spa-like bathroom. The backyard is designed for relaxation and entertaining, boasting a sparkling in-ground pool, spacious sun-drenched deck, and elegant stonework throughout, all set within a private