luxury properties for rent Westhampton Beach, United States

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate guests. Angel Shores is known for its sandy Peconic Bay beach, just a short stroll down the road, perfect for easy beach days and watching sunsets by the water. The home is also conveniently close to Southold’s wineries, farm stands, and village amenities, putting the best of the North Fork right at your fingertips. 2026 Availability: June 16-June 30th $7,000, July $23,000, August $25,000 August-Labor Day $27,500. Permit # 0956

Your quintessential North Fork summer starts here. Tucked away in the quiet beach community of Paradise Shores, this Bayfront cottage is the summer retreat you’ve been dreaming of. Positioned directly on Southold Bay with unobstructed views of Shelter Island, this charming cottage offers the best scenery on the North Fork. Whether you're hosting a sunset dinner or just enjoying a quiet morning, the backdrop is always spectacular. Loaded with vintage charm and coastal energy, it’s a place where the days are measured by the tides rather than the clock. The first floor features a waterfront sunroom, cozy living room, galley kitchen, two bedrooms and a full bath. For ultimate privacy, escape to the second floor, featuring a primary suite with a dedicated sitting area -the perfect perch for morning coffee- and half bath. Step outside to your own secluded paradise where you will find a waterfront deck offering the perfect space for al fresco dining, stargazing, or simply watching the boats pass by. It’s the ultimate front-row seat to the island's beautiful golden-hour. This property has all the markers of a perfect North Fork getaway. Permit #1435. Available Memorial Day-June 30: $18,000, July 1-31: $20,000 and August 1-31: $25,000.

Ground floor one bedroom apartment in Driftwood Cove, steps outside of Greenport Village. Newly renovated with new floors throughout, refreshed kitchen with new stove & refrigerator, freshly painted. Living/dining room with coat closet, bedroom with walk-in closet, full bath, AC. Community laundry with new washing machines & dryers, parking lot. Close to Greenport Village shops, restaurants, groceries, Mitchell Park, waterfront wharf, high school, Jitney, LIRR, and bay beaches. Maximum occupancy 2, no pets, minimum FICA score 650. Driftwood Cove rental application required including background and financial checks. Subject to Board of Director’s approval.

Available Seasonally June 20K, August 16th-Labor Day15K, Available September 15K and October 15K TIMELESS TRANQUALITY ON GARDINERS BAY - An inviting seasonal beachfront retreat on Gardiners Bay, thoughtfully designed as a peaceful escape from the demands of everyday living. Begin your mornings with beautiful sunrises over the water and settle into the quiet rhythm of bayfront living throughout the day. The home offers an open airy layout with three full sized water-facing bedrooms, updated fully equipped kitchen and baths and comfortable modern amenities throughout. A generous enclosed porch provides a versatile space for dining, working remotely or simply slowing down. Outdoors, a charming portico invites alfresco meals with a gas grill while an outdoor shower completes the experience– an effortless calming setting for refined yet relaxed bayfront living. Fully furnished and equipped with necessary linens and towels. Close to fine dining, golf and a versatile selection of wineries for additional enjoyment and entertainment.

Charming historic Bayfront beach cottage located on Orient Harbor in Orient Village. Featuring 75 feet of private walkout beach, waterside porch, screen bay view gazebo for entertaining. Interior includes wide plank wood floors, renovated baths, spacious kitchen water view living room with wood burning fireplace, 2 ensuite bedrooms for a total of 3 bedrooms/ 2.5 baths. Walk to Country Store, Post Office, Orient Yacht Club, marinas, and other village amenities. Close to renowned Orient Beach State Park & Cross Island Ferry. Available Aug $35,000. Permit# 1374. No showings until after January 15, 2026.

Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered April $6,000; May $6,000; June $15,000; Sept $12,000. Permit #0483.

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.

Beautiful renovated 2-bedroom, 2 full bath home in Orient Village. Open concept – living/dining/gourmet kitchen. Lower level with screening room, office, full bath. Walk from Jitney. Enjoy all village amenities, bay & sound beaches. Close to Orient Beach State Park & Cross Sound Ferry. Available April $5,000; May $5,000; June $7,000; July $15,000; Aug $15,000; Sept $8,000. Permit# 1364.

Recently Remodeled Colonial Home on 2 Acres of Property Overlooking the Nissequogue River with Rocking Chair Front Porch. Many Updates Include New Roof, Siding, Driveway, & Eat In Kitchen. Freshly Painted in March 2026 with Refinished Wood Flooring. Den w Wood Burning Fireplace, Updated Bathrooms, Full Basement, 2 Car Garage. Rear Yard is Surrounded by Mature Trees and is Tranquil and Serene. Nearby are Local Beaches, Hiking Trails, Fine Dining, Local Shopping, and Stony Brook University and Medical Center. Smithtown Schools.

ANNUAL RENTAL - FURNISHED OR UNFURNISHED WATERFRONT HOME. Come and enjoy year round this classic New England waterfront home located in coveted Sachems Head with room for everyone- especially your four legged family members. This wonderful home offers a lifestyle for your whole family to enjoy. There are water views from most every room as well as beautiful outdoor spaces to sit and enjoy the serene surroundings. Private, sandy beach area brings so much value to this home!Classic charm throughout offering 3 bedrooms and two full baths and an outdoor shower. Office area with panoramic water views and a 4th possible sleeping nook are located on the main level. Sweet kitchen opens to the dining area with access to the laundry room and the first of the full baths. Second level offers the primary bedroom with stunning views and two additional bedrooms and a full bath with tub. New composite deck with automatic awning is a perfect place to relax with a good book and take in the sights and smells of the ocean. Gated dog run is an added bonus not typically found in a yearly rental. Enjoy outdoor living well into the fall and again in the early spring with the deck, patio and expansive yard that opens to the Sound. Tranquility at its best and the spectacular summer beach months are just an added bonus!

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich heritage is reflected in its exquisite details, from the enduring beauty of Stony Creek Granite and warm Pecky Cypress woodwork, to the original porthole windows in the grand family room. In the formal dining room, a distinctive ribbed ceiling, designed to evoke the overhead of a classic ship's cabin, creates an unforgettable atmosphere for entertaining. The heart of the home features a generous galley kitchen that balances functionality with style, offering abundant cabinetry, expansive counter space, and dining area with plenty of windows making sure no view is missed. Retreat to the second floor to find six spacious bedrooms, each offering its own unique perspective of the water, while the finished third-floor flex space serves as an ideal game room or private sanctuary. Spread across two manicured acres, enjoy relaxed seaside living with multiple sun porches and expansive patio for gatherings. Take advantage of the Vineyard Place Association amenities, all while being just a short drive from charming downtown Guilford!

Direct Waterfront Academic Rental in Stony Creek Available 9/1/26 - 5/31/27 Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Utilities not included. Spend the month of August in this beautifully appointed home, ideally located to enjoy all that the shoreline has to offer. Available for August rental at $20,000.

Enjoy direct waterfront living in desirable Stony Creek with sweeping views of the Thimble Islands and Long Island Sound. This fully furnished, renovated home features an open floor plan with a spacious kitchen, dining area, and great room, all designed to capture the water views. The main level includes a sitting room and half bath. The second floor offers a primary suite with full bath and water views, a guest bedroom with en-suite bath, two additional bedrooms, and a third full bath. Hardwood and tile flooring throughout. Outdoor features include a front porch and patio overlooking the water. A gently rolling lawn transitions to a natural stone shoreline, complete with a private dock ideal for small watercraft. Located in Stony Creek Village near shops, restaurants, hiking trails, and the Legacy Theatre. Just minutes to downtown Branford, 10 minutes to New Haven, and approximately 75 miles to NYC. Spend the month of August in this beautifully appointed home, ideally located to enjoy all that the shoreline has to offer. Available for August rental at $20,000. Also available for academic rental.

STILL AVAILABLE FOR LAST TWO WEEKS OF AUGUST! Panoramic vistas of Long Island Sound and the East River create a breathtaking backdrop for this sophisticated Madison waterfront retreat. Designed for elevated coastal living, the sun-drenched open floor plan flows effortlessly from the main living spaces to expansive water views beyond. Offering 3 bedrooms and 3 full baths, the home comfortably accommodates 8+ guests with thoughtful design and generous gathering spaces. Enjoy easy access to shoreline beaches, perfect for morning swims and evening strolls along the water, while the private heated pool provides a serene setting for long summer afternoons under the Connecticut sky. Available weekly for the last TWO weeks of August at $8,000 per week. A rare opportunity to experience Madison's shoreline lifestyle at its finest - where timeless waterfront beauty meets effortless summer luxury.

Available for the Sept 2026 through June 2027. This sun- filled colonial has been lovingly restored for easy comfortable living. Open views of the Long Island Sound throughout this home offers room for all. Screened in wrap around porch to enjoy the warm days and nights. Updated kitchen with stainless appliances and large dining nook, mud room, office and dedicated laundry room and half bath all found on the main level. Four levels of living make this the perfect home for multi generations: with a main level bedroom with Queen bed, Primary Suite on the second level with en-suite bath and office nook with a private balcony, second bedroom with bunks -on the third level is the fourth bedroom with twin beds, shared full bath on the second level. Lower level has a rec/play room. Access to the Soundview Association beach.

AVAILABLE FOR THE MONTH OF JULY 2026. SEEKING A 4 BEDROOM FULLY FURNISHED SUMMER RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to a renovated full bath and oversized Kitchen. The three bedrooms are on the 2nd floor with a hallway full bath. The neighborhood is one of the most sought after in Madison; Assoc beach is 2 minute walk, surrounding streets provide plenty of walking / running opportunities, neighborhood is quiet and quaint. The home is close to Town, close to I-95 and easily accessible to all other amenities the Town has to offer.

SEEKING A 3 BEDROOM FULLY FURNISHED ACADEMIC RENTAL IN A MADISON BEACH COMMUNITY? This lovely home, located in the Neck Road area of Madison, with beach rights, is filled with old world charm but with modern conveniences - large Living Room is the entire front of the home, over looking a screened in porch. There is a dedicated Dining Room, 1st floor Den (office) with pull out couch and access to a renovated full bath and oversized Kitchen. The three bedrooms are on the 2nd floor with a hallway full bath. The neighborhood is one of the most sought after in Madison; Assoc beach is 2 minute walk, surrounding streets provide plenty of walking / running opportunities, neighborhood is quiet and quaint. The home is close to Town, close to I-95 and easily accessible to all other amenities the Town has to offer. House is available from September 15, 2026 to May 15, 2027.

DIRECT WATERFRONT with unobstructed views of Long Island Sound. LIFE IS BETTER AT THE BEACH. Available for the month of June. Amazing home to gather with friends and family offering large open floor plan, 5 bedrooms, large 3rd floor rec room, porch for al fresco dining...Don't feel like cooking? Head over to the Madison Beach Hotel & treat yourself to cocktails, lunch, dinner with amazing views. Life is Short...Enjoy Madison at its finest.

Daydreaming about waking up to the sounds of waves and walking to your very own private beach? Make your dreams come true at 118 Middle Beach Road! With 7 bedrooms, 5 full baths, and 2 half baths, this iconic property comfortably accommodates up to 14 guests. The main level is an entertainer's paradise featuring an oversized kitchen, formal dining area, living room with views from every angle, and generously-sized screened-in porch! In addition to six of the seven bedrooms, the second floor features a family room perfect for kicking back and soaking in the expansive views! The third floor is a private retreat with the seventh bedroom and enormous recreation room. Let's also remember the large, water-facing screened-in porch perfect for soaking in the sunrise and sunset each day. Just outside, sun, sand, and saltwater air await you! This is the perfect place to be this summer - schedule your private viewing today and enjoy your own private beach in a few short months! One month for $45,000, two weeks for $22,500 or one week for $12,500. Please reach out to listing agent for most up-to-date availability.

AVAILABLE FOR MONTH OF AUGUST. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms- one king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

AVAILABLE FOR MONTH OF JULY. Relax and unwind for a summer at the beach. This well maintained, 3 bedroom home with vintage beach house charm, has easy access to a private association sandy beach just steps away. The open Living Room and Dining Room with the original wood floors are adjacent to a well equipped and modestly updated kitchen for all of your food preparation needs. There is also a mudroom off the kitchen which includes a shower with hot and cold water, making it easy to rinse off when returning from the beach. A Ductless AC system cools off the whole house. The 2nd floor has three bedrooms- one king (master), one full and one with 2 twin beds plus a full bath with shower. A wonderful, expansive front porch, with screens, is a great place to entertain or read. The spacious back and side yards are perfect for all types of summer games and provide a clear view down to the water! The 2 car garage is perfect for storing lawn chairs and beach gear (provided), as well as bikes. The neighborhood is great for taking walks and bike riding. Easy access to downtown Madison by bike or car. Some pets considered.

WATERVIEW SUMMER RENTAL AVAILABLE FOR JULY ONLY as August is now rented. This quintessential Seasonal Beach Cottage with WATER VIEWS is special The views out over Long Island Sound AND a wonderful wraparound South facing Open Porch to catch the summer breezes are both part of this charming Cottage, located directly across from the very desirable private Overshore (SANDY) Beach Association with it's large grass play area, boardwalk, gazebo & even a raft!, Besides the water views from every room, a light & bright open floor plan, high ceilings, a small but cool sleeping porch/room, new ceiling fans, updated Bathrooms, full size washer & dryer and an outside hot/cold shower, the Kitchen has granite counters, stainless appliances including a dishwasher & a butler's pantry. Also OFF SEASON in May & June or September & October possible too at a lesser rate. One time $350 cleaning fee. Sleeps 9.

EXCITING NEWS! This absolutely darling academic rental is unexpectedly available as Tenant had a change in plans. Fully furnished 1 bedroom 1 bath carriage house apartment available for rent SEPTEMBER 2025 - JUNE 2026. This 2nd floor unit overlooks a beautifully manicured backyard and features a private entrance and ample off street parking. Enjoy the walk to beach and downtown as this rental is prime location here in Madison! Completely renovated with modern fixtures, the Upper Deck is one of the prettiest and well kept rentals. Kitchen is updated with modern finishes and opens to the living / family room area. The bedroom is nicely sized with a queen bed and ample closet space. The full bath has been renovated and features a stackable washer dryer. This rental does not last! Landlord covers snow removal, lawn care, trash, WIFI and Cable. Tenant covers for electricity and water. No smoking. EXCELLENT credit required. Ideal only for single person or couple based on septic size. Two months security required.