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Vacation Rentals in Southold, NY

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    All 17 Rentals in Southold
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    Travelers to Southold are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 17
    5 of 5 stars (11) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    $225
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    $300
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 / 13
    1 of 5 stars (1) Terrible
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Waterfront
    • Dishwasher
    • Refrigerator
    • Water Views
    • Satellite TV
    • Stove
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    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
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    Southold, North Fork 11971
    1 of 5 stars Reviewed September 2, 2012
    The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was...
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 4
    other travelers have booked this property
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    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Waterfront
    • Refrigerator
    • Water Views
    • Patio
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    About this property
    This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
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    Southold, North Fork 11971
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 6
    other travelers have booked this property
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    Amenities & Details
    • Housekeeping...
    • TV
    • Watersports Nearby
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    About this property
    This charming cedar shingled beach cottage is located 45 feet from Long Island Sound with steps leading down to its own private beach. The cottage is surrounded by a wood deck perfect for watching spectacular sunsets...each night, a unique palette of pink, blue and violet sky as the sun drops into... View all property information
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    Southold, North Fork 11971
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    $325
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Linens Provided
    • Towels Provided
    • Private Yard
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Southold, North Fork 11971
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    1 / 5
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • TV
    • Waterfront
    • Central Heating
    • DVD Player
    • Water Views
    • Wi-Fi
    • Watersports Nearby
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • 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
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    Location Information
    Southold, North Fork 11971
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    $250
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    1 / 11
    4.5 of 5 stars (2) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Patio
    • Refrigerator
    • Grill
    • Satellite TV
    • Stove
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
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    Location Information
    Southold, North Fork 11971
    4 of 5 stars Reviewed August 22, 2014
    my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
    5 of 5 stars Reviewed August 26, 2013
    We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
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    $1,300
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    1 / 19
    5 of 5 stars (9) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Patio
    • Satellite TV
    • Washer
    • DVD Player
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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, and... View all property information
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    Location Information
    Southold, North Fork 11971
    5 of 5 stars 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 stars 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 / 19
    5 of 5 stars (4) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Deck
    • Water Views
    • Satellite TV
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
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    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed July 14, 2015
    We had such a great time at the Old Bay Home. The kids especially enjoyed having lunch on the terrace and deer and rabbits just walking in and out of the lovely garden. My mother...
    5 of 5 stars Reviewed June 5, 2015
    we were looking for an escape from Brooklyn for our son and his wife. they joined us and were thrilled at the quiet and peacefulness. The front porch is a terrific place for...
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    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Deck
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • Dryer
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable... View all property information
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    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed May 3, 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    $499
    / Night
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • Fireplace
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    • Deck
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and handicapped accessible throughout with wrap around deck, extra wide doorways, new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque... View all property information
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    Location Information
    Southold, North Fork 11971
    From
    $321
    / Night
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    1 / 5
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    • Dryer
    • Waterfront
    • Stereo System
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
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    Location Information
    Southold, North Fork 11971
    From
    $500
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    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Boat Available
    • Stereo System
    • DVD Player
    • Internet Access
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
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    Location Information
    Southold, North Fork 11971
    From
    $250
    / Night
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Internet Access
    • Satellite TV
    • DVD Player
    • Deck
    • Stereo System
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our immaculate waterview beach house is located in a beach and boating community in Southold, New York, only a mile from the historic village of Greenport. It's the perfect place to relax and take in the North Fork's pristine beaches, award-winning wineries, antique shops, art galleries, and... View all property information
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    Location Information
    Southold, North Fork 11971
    From
    $200
    / Night
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    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Patio
    • DVD Player
    • Washer
    • Dryer
    • Air Conditioning
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This charming summer cottage is unique in the sense that it is located in the private community of Reydon Shores, and is just walking distance to a private beach and marina. The special feature is its wrap around enclosed porch with a view of the Peconic Bay. If you enjoy the peaceful country... View all property information
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    Location Information
    Southold, North Fork 11971