luxury house with terrace for rent New Suffolk, United States

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.

2026 Rates: A1-LD $17,500, September $6,500, October $7K Charming Nassau Point Cape Cod. Enjoy sprawling private grounds with community beach access as you enjoy the summer months in this ideal 3 bedroom 2 bathroom escape. The main level features and open dining/, kitchen leading to wood deck, main floor bedroom, full bathroom and living room. The second floor features 2 additional bedroom and 1 full bathroom. Don't let this amazing East End retreat slip away!

2025 Availability & Pricing as Follows: Off Season October 1st - April 30th: $5,500/mo. Memorial Day - Labor Day: $45,000. May (Incl Memorial Day): $10,000. June: $12,000. July: $15,000. August - Labor Day: $18,000. September (not including LD): $10,000. Escape to the North Fork and enjoy the perfect blend of comfort & coastal living in this meticulously maintained 3-bed, 3-full bath home. As you step inside, you'll be greeted by living space adorned with nautical-inspired decor, plenty of natural light, and a gas fireplace. The fully equipped kitchen is a chef's delight, with stainless steel appliances and ample counter space for culinary creations. The open-concept design ensures a seamless flow between the kitchen, dining, and living areas, creating an ideal space for entertaining. Upstairs you'll find the primary king suite with views of Mattituck Inlet and a private spa-like bathroom off the expansive walk-in closet. Two additional well-appointed bedrooms, one w/ a queen bed, the other w/ a full bed, provide plenty of comfort for family members or guests. There's a pull out couch for overflow as well. Theater/media room in the basement, perfect for the rainy days or movie date nights. As you venture outdoors, a pristine landscaped backyard awaits, complete with a patio for outdoor dining, an outdoor BBQ area with a pizza oven, and a cozy fire pit. The home also has a pull out couch for additional overflow, two separate work spaces for those who need to work while on vacation, and split zone Sonos speakers throughout the house and in the backyard. Conveniently located near sought after Love Lane, several renowned wineries, farm-to-table restaurants, several local beaches, and more. Seize the opportunity before someone else does!

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with 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!

Offered June $10,000 ($2,500/wk); July $20,000 ($5,000/wk); Aug $25,000 ($6,250/wk); Sept $12,000 ($3,000/wk); Oct $10,000 ($2,500/wk). Two-week minimum. This contemporary waterfront home on Great Pond enjoys sunrise over the water and spectacular sunsets over Long Island Sound from its hilltop setting in one of the North Fork’s most distinctive beach communities. Surrounded by native plantings and filled with natural light and cooling breezes, the home is designed for effortless indoor-outdoor living. Spanning three floors and 2,600 square feet, it features 3 bedrooms, 4 full baths, and multiple spaces for gathering, entertaining, or quiet retreat. Enter from the spacious front deck, with seating for four and views of lush natural landscape and Sound. The main level comprises an open-plan living room with a wood-burning fireplace, dining area, eat-in kitchen, TV room, full bath, and a rear deck with dining table for six overlooking Great Pond. The ever-changing landscape of water, sky, and birdlife makes this a haven for nature lovers. Upstairs are two ensuite bedrooms, both enjoying beautiful water views and brand-new bathrooms, the one in the master suite benefiting as well from a long bathtub. The garden level offers a third bedroom, full bath, laundry area, movie and screening room, and an office/den with glass doors opening onto a rear deck with lounge chair, sauna, and outdoor shower. A private path leads directly to Great Pond, where kayaks and a canoe await exploration. Additional amenities include bicycles, a massage chair, piano, binoculars, telescope, and EV charger. Kenney’s Beach and the beloved Little Fish restaurant are just a short bike ride away, creating an exceptional blend of comfort, privacy, and outdoor adventure in the heart of the North Fork.

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.

Offered for July $22,000; Aug $22,000; July-Aug $40,000; Sept $10,000. Welcome to the Lemuel B. Hallock Homestead Farmhouse, gracefully set on 2 pastoral acres with lush gardens, mature trees, and private grounds bordering farmland. This meticulously restored home presents an expansive great room with a soaring ceiling, where the living room with a wood-burning fireplace transitions effortlessly into the dining area and spacious eat-in kitchen with a glass door to a patio, perfect for morning coffee. A first-floor ensuite bedroom with a full bath, a wraparound covered porch spanning the front and side of the home, and a laundry room complete the main level. Upstairs, a dramatic two-sided balcony overlooks the living room below and offers two inviting seating areas. Completing this level is a sitting room with bathroom, and two ensuite bedrooms with full baths adding spaces for quiet respite. The home and its grounds are perfectly suited to both sophisticated entertaining and quiet relaxation, creating a setting of enduring North Fork charm. Enjoy the season in this authentic and captivating home.

Classic Cape Cod Retreat Near Shell Beach Enjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 2.5-bath home is set in a friendly, sought-after summer community. The bright, open living and dining area flows seamlessly to a spacious deck, making it ideal for outdoor dining, entertaining, or relaxing after a day at the beach. The spacious kitchen features warm oak cabinetry with white countertops, offering a classic, functional layout that complements the home’s Cape Cod style. The first-floor primary bedroom provides a private and comfortable retreat, ideal for easy living and added convenience. Upstairs, three additional bedrooms offer plenty of space for guests. With nearby beach access, and island activities that Shelter Island has to offer, this home is a wonderful seasonal escape for relaxed coastal living.

Available June $15,000; July $35,000 (RENTED); Aug 17-31 $18,000; Sept $20,000. Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood burning fireplace. Many spacious common areas, including glazed porch connecting the two octagonal wings. Relax on the large water-side deck with hot tub while enjoy panoramic water views from every room. Permit #0465.

Rental is Available in 2026: August $75,000. Located in our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities, top-of-the-line appliances, and walls of windows overlooking Coecles Harbor, this home has no comparisons. With 3,800 sq. ft., the home features an open floor plan with sweeping water views from every vantage point, whether dining, cooking, or lounging. Continue entertaining outside on the large outdoor waterfront deck where you become one with nature. The master and one of the guest bedrooms are en-suite, and the 2 additional bedrooms share a bath. All the bedrooms have abundant closet storage. Enjoy this newly constructed private waterfront property this summer!

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 , July $8,000 , Aug-LD $10,000

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.

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Available Apr $10,000; May $12,000; Sept $20,000; Oct $15,000; Nov $10,000; Dec $10,000. Permit# 1020.

Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16x32 heated pool, newly renovated chef's kitchen & baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling & sliders to pool and deck, eat-in kitchen and dining room with sliders to vineyard deck. Den with pull out queen bed, bedroom with queen bed, 2 full baths, laundry and screened porch complete the ground floor plan. Second floor has 2 additional bedrooms; master with king bed, and 3rd bedroom with 2 full beds, and full bath. Amenities include central air, fully stocked kitchen with Aga stove, high speed internet, TVs with streaming video, gas grill. Walk to Village, Yacht Club & steps to association Willow Terrace bay beach. Embrace the North Fork lifestyle. Offered June $25,000; July $45,000; Aug $50,000; Sept $30,000. Permit #0516.

Offered Sept $8,000. Enjoy the ease of summer on the North Fork in this classic 1910 hilltop home overlooking Orient Bay and Long Island Sound. A three-sided wraparound porch extends the main living spaces outdoors through multiple glass doors, creating a seamless indoor-outdoor flow filled with light and salt breezes. Inside, the home offers inviting spaces for gathering, including a spacious living room with a wood-burning fireplace, a formal dining room, and a generous eat-in kitchen with a butler’s pantry. A TV room/bedroom and full bath complete the ground floor. Upstairs are five bedrooms, including a primary bedroom with a private balcony and half bath, along with a full bath for the four additional bedrooms. The private grounds include an in-ground pool. Latham’s Farm Stand and Orient Village are just a short walk away. September is an ideal time to enjoy this peaceful, timeless retreat.

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.

Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished with master bedroom with full bath plus 2 additional bedrooms & full bath, large gourmet kitchen, den, spacious living room/dining room/common space opening to wrap-around deck overlooking pool. Walk to Village, Latham's farm stand. July 16-30 $15,000; Aug 1-15 $17,500; Aug-LD $35,000. Permit# 0321.

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

Situated in the quaint hamlet of Remsenburg on charming south of the highway Rogers Lane, this fully furnished home is privately nestled on a 1.39 acre waterfront property and completely renovated. The home offers an airy double-height living room with a new propane fireplace, open floor plan, 4 bedrooms, and 2.5 baths. Sliders in the living room and the dining room lead out to the sunny, spacious deck with inground heated pool, Weber grill, outdoor furniture and gorgeous views of the backyard oasis. Enjoy your own private cat walk to the water. 90 minutes from NYC, 10 minutes to village shopping, dining and beautiful beaches.