luxury houses for rent Sag Harbor, United States

Sited south of the highway in Wainscott on historic Sayres Path, this uber-chic cottage is truly a hidden gem. The interiors have been painted beachy white and are highlighted by the incredible wide plank pine wood floors. Tasteful amenities of the first floor include a large open living area centered around a wood-burning brick fireplace, a separate kitchen with modern appliances, a dining area and window seated reading nook, a primary bedroom and full bath. The upstairs loft contains the second sleeping space, complete with a queen-sized bed, two additional twin beds, and a half bath. The quiet side and backyard host a generous lawn, a large deck with a dining table and lounge chairs (ideal for entertaining), as well as an outdoor shower, artfully tucked away under a towering oak. Available off-season from September through June, this home is ideally located near Hampton Jitney transportation and close to fine area shops, local restaurants, and spectacular ocean beaches. [[Rental Registration # 22-212]] EH RR #: 22-212 Rental Terms: Winter Season: $22,000 Per Month April: $5,500

A welcoming first floor with beautiful natural light from the giant sliders welcoming you to the deck with a large and heated pool. Enjoy the privacy protected by lush green trees and bring relaxation to the next level. Upstairs you will find two good sized bedrooms with a shared bathroom. With the outdoor oasis, you likely won't be spending too much time indoors, but if you choose to you will be as comfortable as ever. Washer and dryer are available in the basement so you never have to leave this gorgeous set up!

Authentic 1900s farmhouse only moments to the East Hampton library, Guild Hall, Jitney, and village shops. Thoroughly renovated interior offers a living room, dining room, bright kitchen, and four bedrooms, including one on the first floor. Simply perfect. [[Rental Registration # 01-22VOEH]] EH RR #: 01-22 VOEH Rental Terms: Winter Season: $5,000 Per Month Other / Short Term - Dec: $5,000 September: $15,000 October: $5,000 November: $5,000 May: $10,000 August: $37,500

Diamond contemporary, 4 bedrooms, 3.5 bath, full basement, LR, DR, EIK, IGP, Pool house, won't last!!

This 3 Bedroom, 2 bathroom, modern home is the perfect centrally located Hamptons getaway! A private home nestled into a quiet and friendly neighborhood in close proximity to bay beaches, a few marinas, great hiking trails, and amazing waterfront restaurants.

This just renovated ranch centrally located in Springs offers and incredible stay to its guests. An outdoor shower to cool down from the beach just down the road, a large lawn space for hanging in the evening, and a wonderful deck with a grill to bbq. Thats not all, the inside of this house is immaculate and the layout phenomenal. You will never want to leave this modern gem.

Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023

2024 RATES: JUNE $12,500, JULY $16,000.00 AUGUST $17,000 MD-LD $44,500. Victorian classic in the heart of Greenport Village. Centrally located to all forms of public transportation and close proximity to public Bay beach. This property offers convenience, style and stunning views of Shelter Island and the Peconic Bay. Main features are large front porch, inviting/well appointed living spaces multiple en-suite bedrooms and a large rear yard for entertaining. This historical treasure has been recently updated and provides both the charm of a classic New England port village home and the accommodations of an updated home. Easy North Fork living in Greenport Village.

Cedar Shake Ranch home on Goose Creek, ready for renters starting September 2022! Fully renovated, 4-bed, 2.5-bath. White & bright kitchen, living room, and dining, all in an open floor plan, perfect for entertaining. Move seamlessly through living space and out the sliding glass doors to a well-designed outdoor oasis. Built into a ipe deck is a heated swimming pool with lounge chairs and other seating areas surround. Plus, an outdoor shower and a big grassy yard with beautiful landscape, offering plenty of room for lawn games like badminton or corn hole. From the pool deck enjoy serene views of the water and wildlife. Kayak or stand up paddle board from the private dock or ride your bike to South Harbor Park beach or Croteaux Vineyards. Fully equipped home office/den space and exercise area with a Peloton bike in the basement. Available: Sept(not incl LBD):$12k, Oct:$8k, Nov 2022-April 2023:$4k/mo, May 2023(not incl MD):$8k, May 25, 2023 - end of June 2023:$18k, July 2023:$25k

2024 Rates JULY 32,500 Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Pristine and newly renovated craftsman home in Nassau Farms. Easy access to Nassau Point Beach. Bright and sunny great room with open floor plan; kitchen featuring granite counter tops, custom cabinetry, and high end appliances. Private backyard with bluestone patio, built-in outdoor sound system, stone fireplace, and outdoor cooking. Ideal vacation home on the North Fork. Private path to nearby kayaking. Convenient to all North Fork activities. **Please call for off season rates** Permit # 0283

Bates Masi's renovation and expansion of Harry Bates's 1967 house in East Hampton, New York, salvaged much of the home's original cypress decking and incorporated subtle additions to the exterior. The main living area boasts skylights that allow for just perfect light filtering in. The interior has a slatted motif throughout reminiscent of a ship. This home has been published in numerous design magazines both for its thoughtful renovation and for timeless design. From Dwell - This sleek kitchen hits warm notes with red lacquered cabinetry, cypress woodwork, and a leafy backyard vista...The extra space from the stairway addition allowed for an equally wide, handsome blue sandstone shower. The blue sandstone, which hails from northern New York, is one of three elements chosen for their minimal palette. The patio, kitchen, and bathroom run together along an east-west axis, each room bearing a different finish of the same blue stone. This allows for a subtle contrast in texture, but it also carries the overall theme throughout the space, making it feel more expansive yet sharply defined. There is beach access for residents of Barnes Landing just a quick moment away. A recently added barrel sauna completes the rental experience. [[Rental Registration # 22-1000]] EH RR #: 22-1000 Rental Terms: September: $15,000 July: $30,000 Winter Season: $5,500 Per Month

Experience serenity at this stylishly renovated and tastefully adorned cape in the heart of Greenport village. This expansive residence offers three bedrooms, including a master suite with a private bath, two additional bathrooms, and a convenient home office. The main floor embraces an open-concept design, featuring light-filled dining and living areas, along with a well-appointed kitchen boasting stainless steel appliances. The fenced-in yard creates a tranquil space for stargazing after a day of summer adventures. Just steps away from Greenport Village's restaurants, shops, the Shelter Island Ferry, train, and Jitney bus, and a short distance to popular 67 Steps Beach, this is the perfect location for your unforgettable Greenport summer getaway.

Spend your summer enjoying all the North Fork has to offer at this Greenport waterfront home with dock and community bay beach. Completely updated with high end touches throughout including chef's custom kitchen with island, 3 bedrooms (2 are en-suite), 4 full bathrooms, expansive waterfront deck, and a lower level entertainment lounge. The perfect place to relax and unwind.

Summer 2024 Rates: May24-June30 $20K, July2-Aug1 $30K, Aug2-Sept3 $35K, Sept4-Oct4 $15K: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport and a short drive from all the major North Fork sights. Or just whittle away your days enjoying the amenities of your luxurious home retreat. Lounge in your heated saltwater pool while sipping a cold drink. Curl up with a book in front of your gas fireplace. Catch up on sleep surrounded by plush bedding on your memory foam mattress. Immerse yourself in the low-key North Fork lifestyle at your private Greenport Getaway.

Relax and enjoy this beautifully appointed bay front house w/ private beach and stunning views of Orient Harbor, Bug Light and Shelter Island. Moor your boat in the bay; kayak, swim, fish or chill on the decks and porches. Basement game room w/ Ping-Pong, TV and games. Conveniently located near shopping, restaurants, ferries, farm stands, vineyards.

In the heart of Southampton Village, this property is walking distance to shops and restaurants. Renovated and beautifully furnished, offering 4 bedrooms, 4 1/2 baths, generous living spaces, and a gorgeous screened in porch overlooking the backyard. New heated gunite pool and hot tub, surrounded by blue stone, outdoor shower, bbq, and pool house with TV, AC, and full bathroom. Everything you need for the perfect stay this summer in the most convenient location! Rental Terms: Winter Season: $70,000 Per Month

Charming exquisitely restored mission style cottage with unique privacy. Original beach stone fireplace, custom woodwork throughout, large deck, screened porch, 2 ensuite bedrooms, studio / office, gourmet kitchen and period furnishings. Walk to 2 beautiful sound beaches. July $15,000; Aug $15,000; Aug-LD $17,000. Permit# 1003.