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Vacation Rentals in Southold, NY and nearby

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    1 / 25
    5 of 5 bubbles (16) Excellent
    Southold
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 bubbles (2) Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 34
    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    5 of 5 bubbles (9) Excellent
    Southold
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Porch
    • Satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy,... View all property information
    Location Information
    Southold, North Fork 11971
    5 of 5 bubbles Reviewed July 1, 2015
    My husband and I just stayed in this beautiful house with two friends who are a couple. The photos of the house on this site are accurate and, for once, we were not at all...
    5 of 5 bubbles Reviewed August 18, 2013
    This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
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    1 / 21
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
    • Waterfront
    • Shared Yard
    • Outdoor Dining Area
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 14
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Secure Parking
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system.... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 18
    Southold
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Ocean Views
    • Porch
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 5
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • DVD Player
    • Waterfront
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town lifeguards. Designed to maximize the beauty of its pristine surroundings, the entire back of the house has French doors opening onto a... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 14
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Yard
    • Wi-Fi
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Families will love the location of this two bedroom spacious country home just a short walk to a private sandy Shelter Bay beach along a quiet country dead end road, so no through traffic and safe for bicycling, children and walking the family pet. We are glad to be able to welcome your dog, as we... View all property information
    Location Information
    Southold, North Fork 11971

    The following rentals are within 5 miles of Southold, North Fork, Long Island, New York.

    1 / 14
    5 of 5 bubbles (7) Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Balcony
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes, I do not charge resort fees... View all property information
    Location Information
    Greenport, North Fork 11944
    4 of 5 bubbles Reviewed October 15, 2016
    That's it! Unit was clean and comfortable. Beach was right there. Drive to town or spots of interest easily. Compact, well organized, nice little terrace overlooking the water...
    5 of 5 bubbles Reviewed August 4, 2016
    The condo was very comfortable. Greenport is a great town with lots of restaurants and shops. There are many vineyards right in the area and you couldn't get any easier access to...
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    1 / 18
    5 of 5 bubbles (9) Excellent
    Cutchogue
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Outdoor Dining Area
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Central Heating
    • Parking
    • Private Yard
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Cozy Cutchogue Beach Cottage on the North Fork of Long Island. It has 2 bedrooms with queen sized beds and there is a sleeping loft appropriate for children over 9 years old (one queen sized bed and one twin). Deck and backyard with gas grill, outdoor picnic table, fire pit, and tire swing.... View all property information
    Location Information
    Cutchogue, North Fork 11935
    5 of 5 bubbles Reviewed August 23, 2016
    We had a very happy stay here. Contact with Julie was first class, the house is very tastefully decorated and comfortable. It is ideally situated to explore further but has...
    5 of 5 bubbles Reviewed August 8, 2016
    We so enjoyed our time here. You really can't find a more homey cottage and the close proximity to the great beach and scenic hilltop playground was tops. Julie was wonderful to...
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    1 / 11
    4 of 5 bubbles (5) Very good
    Greenport
    3 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Outdoor Dining Area
    • Porch
    • Shared Yard
    • Waterfront
    • Internet Access
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our one bedroom has 3 rooms + kitchenette. The parlor with convertible couch ( Standerd double ) sleeps two. Our Bedroom has a Queen Size Bed. Porch & Backyard garden. We are just forty yard walk to our block pier. 150 yard walk into town. The heart of Greenport Village. Bay House is on the best... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed July 11, 2016
    So close to everything! The place is in a great spot. Downtown Greenport is a block away and you would never know it. Very quiet and clean space for my wife and I to enjoy our...
    5 of 5 bubbles Reviewed May 4, 2016
    Great location, easy walk to town and right next to a pretty dock. If you travel with 4 you have to walk through the room with fold out bed to reach bathroom so might be better...
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    1 / 25
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 10
    4 of 5 bubbles (1) Very good
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Secure Parking
    • Satellite TV
    • Private Yard
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport... View all property information
    Location Information
    Greenport, North Fork 11944
    4 of 5 bubbles Reviewed 2 weeks ago
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    1 / 17
    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • DVD Player
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    • Grill
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    • Air Conditioning
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    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature!<BR>Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is... View all property information
    Location Information
    Peconic, North Fork 11958
    1 / 20
    Shelter Island Heights
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Grill
    • Satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Internet Access
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your... View all property information
    Location Information
    Shelter Island Heights, Shelter Island 11965
    1 / 23
    4.5 of 5 bubbles (3) Very good
    Greenport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Housekeeping...
    • DVD Player
    • Balcony
    • Satellite TV
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed September 23, 2014
    The pictures of this house do not do it justice. It is spacious although an older home, with wide floorboards, a great room with fireplace, toys for kids, deck for eating or just...
    4 of 5 bubbles Reviewed October 14, 2013
    We just returned from renting for Columbus weekend. Very happy with the house. We needed a ground floor room & shower for my 88yr old Mother & this worked out perfect. A few steep...
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    1 / 18
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Private Yard
    • Parking
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 14
    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    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.... View all property information
    Location Information
    Cutchogue, North Fork 11935
    1 / 8
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Parking, beach access, convenient... View all property information
    Location Information
    Greenport, North Fork 11944
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    1 / 13
    Greenport
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Balcony
    • Porch
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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, grill, and al fresco dining under a pergola. Located in Greenport, NY, the middle of wine... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 12
    4.5 of 5 bubbles (24) Very good
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • Internet Access
    • Terrace
    • Private Outdoor...
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed September 2, 2014
    6 Girlfriends with children wanted a quick easy trip with no traffic to end the summer. We got exactly that! The Cliffside Resort was perfect. I honestly can't say what I liked...
    5 of 5 bubbles Reviewed June 10, 2014
    My son got married this past weekend at a Vineyard near Cliffside and my family, the bride's family and some guests spent the weekend there. In total, we rented about 23 units...
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    1 / 16
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Parking
    • Grill
    • Children's Pool
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 8
    5 of 5 bubbles (33) Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Air Conditioning
    • Terrace
    • Internet Access
    • Satellite TV
    • Waterfront
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at... View all property information
    Location Information
    Greenport, North Fork 11944
    5 of 5 bubbles Reviewed July 2, 2015
    My college friends & I have been coming here for @ 6 years...nowhere better....the condo is clean and nicely decorated......if you choose water view/front...well worth the extra...
    5 of 5 bubbles Reviewed August 6, 2014
    Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool with...
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    1 / 16
    Greenport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    About this property
    Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 24
    Greenport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Internet Access
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    NEW!!! PRIVATE BEACH FRONT HOME - 3 bedroom, 3 bathroom, Walk to town - 1 block RARE! One of a kind opportunity to rent a PRIVATE BEACHFRONT HOME with 250 feet of Sandy Beach! Our newly renovated custom beachfront home has all BRAND NEW FURNISHINGS - NEVER USED BEFORE including mattresses,... View all property information
    Location Information
    Greenport, North Fork 11944
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