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300+ Rentals · Southold
300+ Rentals · Southold
RARE! One of a kind opportunity to rent a PRIVATE WATER VIEW HOME! Our newly renovated custom home is located in the heart of Greenport Village. Walk 2 blocks to restaurants and shops in town. Breathtaking views of the bay. CUSTOM RENOVATION! Learn More
This house is a beautiful WATER VIEW 2 story vintage 1870's historical home located in the Village of Greenport. It has been fully renovated with custom amenities. The Interior is nautical themed with Restoration Hardware furnishings including Belgian linen, leather couches. The custom gourmet kitchen is picture perfect. A gorgeous blend of wood and tiles that creates the perfect place to gather and to entertain. You will fee as if you've stepped into a pottery barn / restoration hardw...
Nestled on the bluffs overlooking the Long Island Sound, is reinventing the North Fork! Quaint villages, fine restaurants, and exquisite wineries add to the splendor of the beautiful scenery. Whether staying for a couple of nights, or a couple of weeks, our Greenport condo can’t be beaten for location! Learn More
Furnished for comfort and relaxation, our unit is decorated and equipped in a modern fashion. Kitchenettes contain cooking utensils, pots, pans, silverware, glassware, and dinner ware. Enjoy complimentary wireless internet, individual air conditioning, and flat screen televisions in all bedrooms Incredible Sunset & Views Direct Beach Access Sliding Glass Door to Private Deck Heated Outdoor Pool Complimentary WiFi Furnished Accommodations Full Kitchen Amenities Private Beach Air ...
Long Island Wine Country, Pumpkin & Christmas Tree Farms, Beaches, Boating, Shopping, Cafe's, Art Galleries, Biking, Night Life, Dancing, Tours, Fishing, Boutiques, Ice Cream Shops, Famous Carousel, Dockside Dining & Entertainment, Ice Rink Learn More
Second floor apartment in the heart of the Greenport Village where all the action takes place! Walking distance to top rated restaurants, clam bars, art galleries, boating, beaches, swimming, biking, Greenport’s own carousel, brewery, tea and coffee cafes, live music, dancing, night life, ice cream shops, boutiques, grocery shopping, farmers market, local farm stands, tour rides, and wine tasting! A short distance from several local seafood markets. Something for people of all ages! This...
New house with private beach access and a 5-min drive to historic downtown. This 4 bed, 4 bath sleeps up to 10 and features two masters. Large common areas for cooking, eating and vegging out with a 55" flatscreen. Large yard for BBQs and relaxing. You'll love your stay! Learn More
The house is in a nice beach community neighborhood with great access to town and recreation. Plenty of parking at the house. Manhattan to downtown Greenport via Hamptons Jitney and LIRR. Details: - Private access to neighborhood beach 3 blocks away - Beach towels - Bath towels - Iron - Ceiling fans in all bedrooms - Pull-out sofa in den area (sleeps 2) - King-size beds in master bedrooms (2) - WiFi - Wireless keypad entry - Fully equipped kitchen - 55" TV - Games - Washer/dryer - Charco...
Grand house from 1850. There are 3 available bedrooms with a shared bath. The house sits on three acres of award winning landscaped garden, short walk to golf course, restaurants, library and Hampton Jitney Stop. Close to great library, beaches and wineries as well. Lovingly prepared breakfast and parking included. Learn More
Unique historic home in award winning garden Golf, beaches, town center, restaurants, wineries, Hampton Jitney Stop. I love to talk with my guests and pass on local tips for travelers. NOFO - the Long Island North Fork part is a rural paradise where time has stood still. Close to bus stop, great for biking. I make a lovely breakfast
RARE! One of a kind opportunity to rent a PRIVATE BEACHFRONT HOME! Our newly renovated custom is located in the heart of Greenport Village. Gated, private, quiet. Walk 2 blocks to restaurants and shops in town. Breathtaking views of the bay. Learn More
Our newly renovated custom home is all on one level, set back behind gates that open and close upon entrance. Private driveway with 2 car garage. The gorgeous beachfront home is equipped with all the modern amenities yet in the historic village of Greenport. The modern kitchen and family room is separated by a gorgeous glass fireplace that turns on with a switch of a button. All rooms have panoramic views of the bay. There is wifi and cable tv throughout the house. The sliding glass d...
Beautiful summer rental available on Long Island’s North Fork. Three-bedroom cottage located in Cutchogue, NY. -The heart of wine country -Sleeps six to eight -Indoor and outdoor showers -One block from lifeguard-protected beach Learn More
Beautiful summer rental available on Long Island’s unspoiled North Fork. Three-bedroom cottage located in Cutchogue, New York, in the heart of wine country; sleeps six to eight; indoor and outdoor showers. The cottage is one block from a lifeguard-protected beach on Little Peconic Bay. Local attractions include swimming, fishing, boating, kayaking, numerous wineries, fruit and vegetable farms, outlet shopping (one half-hour away), Splish-Splash water park (one half hour away), the fishin...
Grapefields has undergone massive improvements this past winter. All spruced up, it is waiting for you to come and enjoy your private cottage away from home in exclusive Nassau Point. Learn More
Beautiful Cottage located on prestigious Nassau Point. Steps to Bay Front beach. As much or as little as guests would like! Grapefields underwent sprucing up this last winter and is fresh, comfortable and luxurious.
Explore Long Island Wine country. Peaceful, private, relaxing, comfortable, super clean and spacious studio apt. with private bath, private balcony, close to all. Walk to vineyard, bike to beach. Learn More
Huge, modern, eco friendly guest studio suite in luxury private home. Self contained with separate entrance, private bathroom and private outdoor terrace with woodland views. We provide quality linens and towels, including European duvet with linen covers, freshly laundered between guests, not blankets. The suite has CAC (central air conditioning) as well as ceiling fans, and is fully heated with its own thermostatic controls. There is a 36" LCD TV, no Cable TV, but media player with Netf...
Charming, sunny 2,300 sq. foot home in a quiet corner of downtown Greenport. This 1890's house has 4 bedrooms, 2 bathrooms and an eat-in kitchen overlooking a large, gracious fenced in yard. Just steps away from Greenport's finest! Family friendly!!! Learn More
Starting June 22, we will be requiring a 5 night stay for the rest of the summer. May be able to make certain accommodations for mid-weeks and therefore have a few weekends available. Always ask! :) Charming, sunny and spacious 2,300 sq. foot home with 4 bedrooms and a gorgeous yard in a quiet corner of downtown Greenport. Built in 1890, this home features impeccable hard wood floors, beautiful tin ceilings and walls and an adorable window seat- all within steps of Greenport’s finest. This...
Nestled in the heart of the North Fork this chic Cutchogue farm house is comfortable and spacious. It sleeps up to 9 adults with it's 4 large bedrooms. The guest bathroom has been renovated and features a reclaimed barn wood vanity and marble shower. The chefs kitchen was also recently remodeled and has a 5 burner gas range and wine fridge. But you won't just fall in love with the inside. The yard provides 2 very private acres, with a refurbished horse barn for outdoor entertaining. Learn More
Grand house from 1850. There are 3 available bedrooms with a shared bath. The house sits on 3 acres of award winning gardens, short walk to golf course, restaurants, library, museum, and Hampton Jitney stop. Close to beaches and wineries. Learn More
Lovingly prepared continental breakfast on spacious porch overlooking gardens. Free parking. Small pets welcome. Private room and porch area, entire grounds of property. Yes, we are available for any questions or needs that may arise. We are about two walking blocks from downtown Cutchogue, on the Main Road. We are walking distance to the Jitney stop. No smoking in house or porch.
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Relaxing, comfortable B&B in the heart of the North Fork. Enjoy the vineyards, beaches and farms and revive in a cozy little farmhouse. The Florentine room offers a soft Queen bed with own private bathroom. Learn More
Newly renovated room with en suite bathroom. Sip coffee on the front porch. Kick back on the back deck and enjoy the views of the North Fork Country Club golf course. Common areas are available to stretch out and meet the other guests. Wanna find something fun to do? We're here to help you make the most of your stay. Cutchogue is in the heart of the North Fork. It is know as the "sunniest" place in New York. The Hampton Jitney is walking distance away. Drive in or rent a car to get the...
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As part of the strip of historic homes along Main Road in Cutchogue village , this tastefully restored antique cape offers all the charm you seek of a North Fork home with many added conveniences of the village location. Learn More
Renovated, clean and tastefully appointed by architect/owner with upscale amenities. Guests have full house and yard access. I will be available for any questions/communication a guest feels is needed. However, I expect you'll find my notes left for guests sufficient as far as information is concerned. The neighborhood is in the heart of the North Fork and all its known for. Beautiful blocks for evening walks & star gazing, along with views of picturesque country club green and horses/ba...
Gateway to Oregon Road's, Sophisticated Designer's Retro Art drenched 2 Bedroom, 1.5 bath ranch w/ porch on 1.5 acres borders farmland from the front yard, a tree farm from the back yard & vineyard. Ideal for couples or families. Child friendly! Learn More
Chic, ecclectic and comfortably designed for easy living on one floor with designer and retro details makes this home a perfect central location to explore the North Fork's beaches, vineyards, villages and nature or have a getaway. The house sleeps 6 with the Queen sleeper couch in the living room. Ideally two couples with a guest can sleep comfortably or a family of four for shorter stays. For longer stays, a family of three with an occasional guest. Whether a couple, couples or for a...
This 3 bedroom home with pool is 1 mile from the bay and surrounded by vineyards. Close to shopping, restaurants and the North Fork's beautiful wineries . Perfect for all seasons. Learn More
Perfect family vacation home and those seeking a quiet relaxing setting. Guests will have access to the complete home, deck, pool, grill and beach privileges Completely private to renters The bay is I mile away and you are able to walk to Main Street. Accessible by LIRR at Mattituck Station. Please inquire about special pricing Guests will have access to the complete home, deck, pool, grill and beach privileges. Completely private to renters The bay is I mile away and you are ab...
Take it easy in the Over Easy Room!!! Sleep in a comfy bed and relax in your private pedestal tub. Recharge for the adventures that await on the North Fork... Learn More
A truly one of a kind B&B offers a great place to stay and and awesome breakfast to start your day. Sit back and watch the world go by on the front porch or relax on the back deck. There are many guest areas both inside and out to relax and enjoy. Wanna know what's around. We're here to help you make the best of your stay. Cutchogue is known as the "sunniest place" in New York. Come see the local wineries, beaches and farms. There's a little bit of everything. Feel like shopping? Check...
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Sunny, large, 2,000 square feet, beautiful and spacious 4 bedroom second floor apartment in the HEART of downtown Greenport! Located on Main Street steps from the water! Everything inside this apartment is BRAND NEW! Experience a modern, hip feel in a historic, classic Greenport building! Enjoy beautiful Marina, Mitchell Park and Shelter Island views from the kitchen and bathroom! This recently upgraded early 20th Century building is full of charm. Steps from Noah's, Scrimshaw,The Frisky O...
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