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Vacation Rentals in Southold, NY

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    From
    $431
    / Night
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    2 Bedrooms, 1 Bathroom, Sleeps 5
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    From
    $331
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    2 Bedrooms, 1 Bathroom, Sleeps 4
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    From
    $464
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    From
    $298
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    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    • Internet Access
    • Refrigerator
    • Private Fishing...
    • DVD Player
    • Waterfront
    • Water Views
    • TV
    • Fireplace
    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
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    $331
    / Night
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    1 / 13
    1 of 5 stars (1) Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Waterfront
    • Dishwasher
    • Refrigerator
    • Water Views
    • Satellite TV
    • Cooker
    • 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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    Location Information
    Southold, North Fork 11971
    1 of 5 stars Reviewed 2 September 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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    $391
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    1 / 17
    5 of 5 stars (11) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6
    other travellers have booked this property
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    Amenities & Details
    • Private Fishing...
    • Deck
    • Water Views
    • Fireplace
    • Air Conditioning
    • Waterfront
    • Stereo System
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and... View all property information
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    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed 28 August 2014
    We had such a wonderful time in Maureen and Alan's cottage. First and foremost, it's on Arshamomaque Pond, which looks like a lake but is actually an inlet of Peconic Bay. It's...
    5 of 5 stars Reviewed 13 July 2014
    My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
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    From
    $298
    / Night
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    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    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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    Location Information
    Southold, North Fork 11971
    From
    $398
    / Night
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other travellers have booked this property
    Overview Make Enquiry
    Overview
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
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    Location Information
    Southold, North Fork 11971
    From
    $762
    / Night
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    5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Overview
    Amenities & Details
    • Water Views
    • Waterfront
    • TV
    • Ocean Views
    • Wi-Fi
    • Watersports Nearby
    • Water Park Nearby
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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
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    Location Information
    Southold, North Fork 11971
    From
    $663
    / Night
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    1 / 19
    5 of 5 stars (4) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Reviews (4) Make Enquiry
    Overview Reviews (4)
    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 14 July 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 5 June 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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    From
    $1,723
    / Week
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    1 / 19
    5 of 5 stars (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (9) Make Enquiry
    Overview Reviews (9)
    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 1 July 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 18 August 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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    From
    $425
    / Night
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    1 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Waterfront
    • Dryer
    • Washer
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $265
    / Night
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    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dryer
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
    • Patio
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $391
    / Night
    View Details
    1 / 11
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Patio
    • Deck
    • Dryer
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Air Conditioning
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $663
    / Night
    View Details
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Water Views
    • Air Conditioning
    • Stereo System
    • DVD Player
    • Hot Tub
    • Boat Available
    • Satellite TV
    • Internet Access
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $391
    / Night
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    5 of 5 stars Reviewed 3 May 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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    From
    $661
    / Night
    View Details
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $661
    / Night
    View Details
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Washer
    • Fireplace
    • Waterfront
    • Dryer
    • Satellite TV
    • Deck
    • Internet Access
    • Air Conditioning
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $425
    / Night
    View Details
    1 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $331
    / Night
    View Details
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
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    From
    $265
    / Night
    View Details
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $331
    / Night
    View Details
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Washer
    • Deck
    • Stereo System
    • Satellite TV
    • DVD Player
    • Internet Access
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    Enquire for rates
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971