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.

Holiday Homes and Apartments 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
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $482 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travellers to Southold are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    5 of 5 stars (15) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 17
    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 19
    5 of 5 stars (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    1 / 19
    5 of 5 stars (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Porch
    • DVD Player
    • Satellite TV
    • Grill
    • Air Conditioning
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    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...
    4 of 5 stars Reviewed 17 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
    1 / 18
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • 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
    1 / 21
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Shared Garden
    • 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
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    • 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
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • 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
    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Air Conditioning
    Suitability
    • 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
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Balcony
    • Wi-Fi
    • Ocean Views
    • Washer
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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
    Location Information
    Southold, North Fork
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    1 / 34
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Waterfront
    • Parking
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for... View all property information
    Location Information
    Southold, North Fork
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Porch
    • DVD Player
    • Patio
    • Grill
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    1 / 11
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    5 of 5 stars Reviewed 4 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
    1 / 5
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Amenities & Details
    • Parking
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Southold, North Fork