We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Southold, NY

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 19 Rentals in Southold
    loading...
    Travellers to Southold are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $368
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (11) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Reviews (11) Make Enquiry
    From
    $262
    / Night
    Payment Protection
    View Details
    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    From
    $375
    / Night
    Payment Protection
    View Details
    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    From
    $312
    / Night
    Payment Protection
    View Details
    1 / 13
    1 of 5 stars (1) Terrible
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
    Make Enquiry
    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...
    See all reviews
    From
    $281
    / Night
    Payment Protection
    View Details
    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $2,998
    / Week
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (2) Excellent
    2 Bedrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    **New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $406
    / Night
    Payment Protection
    View Details
    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • 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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $312
    / Night
    Payment Protection
    View Details
    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Housekeeping...
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    From
    $312
    / Night
    View Details
    1 / 11
    4.5 of 5 stars (2) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    4 of 5 stars Reviewed 22 August 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 26 August 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...
    See all reviews
    From
    $1,624
    / Week
    View Details
    1 / 19
    5 of 5 stars (8) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    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...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $624
    / Night
    View Details
    1 / 19
    4.5 of 5 stars (2) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    Make Enquiry
    Location Information
    Southold, North Fork 11971
    4 of 5 stars Reviewed 16 June 2014
    We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
    See all reviews
    From
    $368
    / Night
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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...
    See all reviews
    From
    $624
    / Night
    View Details
    1 / 12
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This beautifully manicured family home features bay views, 4-bedrooms, 3-bath 3400 sq foot home is located in a quiet enclave in Southold. Boasting a stylish light-filled lower level which includes : vaulted ceiling entrance hallway leading up to staircase, living room with fire place , spacious... View all property information
    Make Enquiry
    Location Information
    Southold, North Fork
    From
    $623
    / Night
    View Details
    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
    $401
    / Night
    View Details
    1 / 5
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    $624
    / Night
    View Details
    1 / 16
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    $312
    / Night
    View Details
    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
    From
    $250
    / Night
    View Details
    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
    $368
    / Night
    View Details
    1 / 10
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Newly renovated waterfront cottage with detached studio This property consists of two separate buildings, a two bedroom house with Queen, two twins with pullout beds and the detached studio cottage with queen bed . From September through June only the studio (sleeps 2 + cot for child) is... View all property information
    Make Enquiry
    Location Information
    Southold, North Fork 11971