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300+ Vacation Rentals · Southold
300+ Vacation Rentals · Southold
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.
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.
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!!!
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...
Our adorable 2 BR cottage in the heart of wine country in LI's North Shore is impeccably decorated with a separate breezy, sunny dinning room and screened in porch. We are less than 1/2 mile walking distance to two beaches or less via our kayak! Wifi
Charming beach house, impeccably decorated yet still homey, warm and comforting, Kitchen, bath redone; sun room with windows open; rarely need A/C. Close to the beach (1/2 mile), closer to water access for kayak (200 yards), wineries and great restaurants! Just added a Tempurpedic mattress in the master bedroom! Enjoy our beer garden porch! House has a storage attic that is not included. I our garage, find Kayak, bicycles, gas grill, fire pit all included! You have free reign to everything...
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.
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
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.
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...
Refined, contemporary style awaits you in the heart of wine country, just steps away from six local wineries. Newly renovated 1921 home features boutique style gust rooms with private baths, modern amenities and complimentary Wi-Fi.
Our newly designed guest rooms are equipped with organic toiletries, hair dryers and turkish cotton towels. To truly experience the North Fork, we intentionally keep our rooms clean and simple, without Televisions. Complimentary Wi-Fi is always available and Central Air is included from May through September. Common space includes: Dining & living area, front and side porch as well as backyard patio. For your safety Kitchen is private, we’re happy to keep items in the refrigerator for our...
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.
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...
Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or town. With original hardwood floors, modern kitchen with Viking appliances, two fireplaces, and al fresco dining under a pergola.
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!
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...
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!
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...
Magnificently restored 1920 Gadsby Estate in Cutchogue on the Long Island Sound is available for monthly rental. Four bedrooms, four baths, 3400sf, in private beach community with access to private beach, outdoor hot tub and shower. Two week minimum
Centrally located on Long Island sound and between North Fork wineries and farm fields. There is a minimal stay of two weeks as per recent Southold ruling is required. No pets allowed and a professional cleaning fee of $300 is required on top of the rental fee. Bedrooms include two king size beds, one queen and one full with available cots. Private suite. Two full bathrooms and two 1/2 bathrooms
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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.
Well located Greenport 2 family home. Both homes accommodate 12 adults. total 5 bedrooms, 4 baths, 2 newly renovated kitchens, 2 laundry rooms. VERY large open kitchen, living room, sunroom and dining room spaces. BBQ and large yard. Rent homes together or separately.
Newly renovated 2 family in the heart of Greenport Village. A perfect space for a family vacation or a group getaway. All bedrooms have new beds and bathrooms are recently renovated. Very large open kitchen, sunroom, living room and dining room is perfect for entertaining. Large patio and backyard as well as outdoor shower. One home has 3 beds, 2 baths as well as a queen sleeper and the second home offers a separate living space with 2 beds, 2 baths. Each house can be rented separately or ...
This charming schoolhouse, built in the 1880's, has an open floor plan, and is perfect for relaxing and entertaining. The house was updated in 2013, so has all of the modern amenities amidst the old world charm.
The Old Schoolhouse tells a family story, dating back to the 1880's. Although the house is old, it was moved and a new foundation was built in the 1940's to support the structure. The prior owners updated the house in 2005 with the most energy efficient systems, so the charm is intact, but the house is supported by a modern infrastructure. This house has an open floor plan and the light is bright. Perfect place to hang out and relax, cook, read and just enjoy. The three bedrooms are q...
This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath.
This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house. There are a/c units in the bedrooms and living room. The house is located in the middle of wine country and 5 minutes by car from Cutchogue beach on Pequash Ave., off the Main Road, with small park, p...
Newly renovated beach cottage - less than 10 min to 10+ wineries! Near great beaches, fabulous restaurants, farm stands, golf, boating, antiques, yoga & more. Walk the tranquil, peaceful neighborhood, launch our kayaks @ end of block. Relax/enjoy!
Our charming beach cottage has hard wood floors throughout and is bright and airy. It sleeps up to 5 in our 2-3 bedrooms. The 1st bedroom is the spacious master with queen bed, ceiling fan, alcove & walk in closet. The 2nd bedroom is cozy with a full size bed, ceiling fan & closet. We also have a lovely room we call the blue room that during the day is set up with a new queen size sleeper sofa. At night just close the french doors, open the couch to a bed and relax taking in the North F...
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...
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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