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Vacation Rentals In Southold, NY

Showing 20 Of 112 Vacation Rentals

We Have 112 Vacation Rental Offers Available In Southold. Average Price Per Night Is $567.81. Find Your Vacation Home Today.

  • Property-1 Image 1
    Exceptional
    (3)
    Private Vacation Home
    A Natural Getaway
    Southold, New York, United States

    This lovely stroll-to-the beach "farmhouse," built in 2019 on a woodsy acre, is bright, peaceful and centrally-located. The 3-bedroom, 2.5 bath home with an office and a den, is a 1600-square-foot contemporary with an outdoor shower, pebbled patio and front-yard. It is an easy 7-minute walk to pristine McCabes Beach. It's 2 miles to family-friendly Southold village where the Hampton Jitney stops to-and-from Manhattan. A 10-minute drive takes you to the lively Greenport village where 2 short ferry-rides go to The Hamptons. Enjoy the idyllic North Fork here! Please note: A 2-week minimum stay is enforced by the town. Read More

    3 Bed
    4 Baths
    Sleeps 6
    $180 / Nightly
  • Property-2 Image 1
    Exceptional
    (15)
    Private Vacation Home
    Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries
    Southold, New York, United States

    Make yourself at home in this recently renovated home in the heart of the North Fork Wine Country! With three bedrooms and three bathrooms in this 2200 sq. ft. home, there is plenty of room for all! The master features a large walk-in closet and a large master bath with a double sink vanity, free standing tub and large walk-in shower. Enjoy the open concept kitchen and living room adjacent to the dining room and wet bar which is perfect for entertaining. Relax on the rocking chairs on the front porch or the large patio.Roast marshmalllows while enjoying an evening around the fire pit. brbrThe North Fork has a lot to offer. There are numerous wineries, breweries, fine dining and boutiques. The beach is only moments away from this location. Enjoy a short trip to Greenport and enjoy a day of shopping and dining along the harborside. The North Fork is easily accessible to beautiful Shelter Island where you can catch a nice ferry ride over to the Hamptons. brbrThis home has a lot to offer for a great vacation! Read More

    3 Bed
    3 Baths
    Sleeps 8
    $750 / Nightly
  • Property-3 Image 1
    Exceptional
    (3)
    Private Vacation Home
    North fork Private exclusive Residence for Rent
    Southold, New York, United States

    Spacious 3 bedroom ...3 1/2 bathroom modern house with large swimming pool .close to the beach and vine yards. Large eat in kitchen. Wolf appliances.....granite island. dining room ....tv room with bar for entertainment...Reading / Sunroom, With access to a large back grassed yard leading out to a large salt water swimming pool....with bbq....living room and indoor gas fire .... Master bedroom. King bed. Large couch ...large walk in closet and a full bathroom. Second bedroom king bed ...large closet n third bedroom queen bed. All bedrooms have TVs...br Read More

    6 Bed
    3 Baths
    Sleeps 8
    $203 / Nightly
  • Property-4 Image 1
    Private Vacation Home
    Water Front Property
    Southold, New York, United States

    One of a kind fabulous bay front property with dock, large expansive deck, over looking Southold Bay / Shelter Island, short distance from charming Southold Town and a variety of beautiful Bay-side and Sound-side beaches. Read More

    4 Bed
    3 Baths
    Sleeps 12
    $1,200 / Nightly
  • Property-5 Image 1
    Wonderful
    (28)
    Private Vacation Home
    North Beach Fork Beach House
    Southold, New York, United States

    Enjoy our tranquil home in the private beach community of Southold Shores. Located on a half acre of private land, this home has all the amenities you will need for a relaxing vacation or getaway. Views of Peconic Bay from the home, a private beach and marina. Take advantage of Historic Greenport, located just 1 mile away, as well as the Ferry to Shelter Island and Sag Harbor, along with three restaurants just walking distance away.brHome has an open concept feel with catherdal ceilings, great room, kitchen and dining room with sliding glass doors that leads to a large deck. The deck wraps around to the front porch.brNOT A SHARE HOUSE OR USE FOR AFTER PROM.brbr Read More

    3 Bed
    2 Baths
    Sleeps 6
    $343 / Nightly
  • Property-6 Image 1
    Very Good
    (1)
    Private Vacation Home
    Beautiful North Fork 3-bedroom Home Steps Away From a Private Sandy Bay
    Southold, New York, United States

    Beautiful vacation home in the Bay Haven community of Southold. The house is on a fully landscaped property of over a third of an acre, steps away from the community's private sandy bay beach, which may be used by renters. The three-bedroom house, which has central air conditioning, is ideal for a small family or one or two couples, and can sleep up to 6 people. It has a master bedroom with a queen bed, and two additional bedrooms with double beds in each, two full bathrooms, with one en suite in master bedroom, a downstairs bathroom/powder room, family room with skylight, kitchen, living room, full dining room, laundry room with washer/dryer, a covered front porch with seating, and a large rear deck with dining table, umbrella, and barbecue.Three bicycles are available and all beach chairs and umbrellas. The house is minutes away from convenient shopping, beautiful beaches, great restaurants and gorgeous vineyards. Read More

    3 Baths
    $399 / Nightly
  • Property-7 Image 1
    Exceptional
    (9)
    Cottage
    Lovely Waterview Cottage in the Heart of Long Island Wine country
    Southold, New York, United States

    Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and lovely screened in front porch to enjoy the beautiful pond view-watch ospreys fly over, or enjoy the pond by using kayaks, paddle boats or canoe that comes with the rental. 10 minute walk to beautiful sound beach around the corner-minutes to wineries, Southold village, and Greenport. Read More

    2 Bed
    2 Baths
    Sleeps 4
    $248 / Nightly
  • Property-8 Image 1
    Exceptional
    (5)
    Private Vacation Home
    3 minute walk from a private beach!
    Southold, New York, United States

    Newly renovated 4 BR 2 Bath home located on a private street with private beach down the road. 3 Bedrooms on the 2nd floor along with a spacious bathroom. Additional bedroom on first floor with connected bath. Nice open plan is easy for entertaining. Kitchen with island and all new appliances. Views through the slider out to the relaxing backyard where you can grill or catch the afternoon sun. Everything is brand new. Quiet secluded setting yet a quick drive to town. Fifteen minute drive to Greenport where there is shopping and restaurants. You can also catch the ferry there to Shelter Island. Please inquire regarding off season rates and minimum stay. There is a fee of $11 per day for EV car charging. Please notify Host. Read More

    4 Bed
    2 Baths
    Sleeps 12
    $525 / Nightly
  • Property-9 Image 1
    Excellent
    (3)
    Private Vacation Home
    Southold home at Kenney's Beach 4 bedrooms
    Southold, New York, United States

    Lovely, spacious home with open, airy floor plan, featuring four bedrooms at Kenney's beach in Southold. First floor has a two story living room with huge fireplace and skylights. The dining room features a banquet size dining table and sliding doors that lead to an enormous deck with arched built in seating. Deck also wrought iron furniture and a stainless Weber grill. There is also an outdoor shower steps away from a door that opens into a mudroom. The kitchen has granite counters and brand new top of the line stainless steel appliances. Off the kitchen is a mud room with a washer and dryer and a full bathroom. The mudroom accesses the rear deck and garage to the side. First floor also has a large bedroom with a queen bed. Second story has bedroom with balcony facing rear and queen bed. There are two additional bedrooms with two twin beds in each of them and a full bath. There is wifi, cable, internet. Enjoy the most amazing sunsets at one of the nicest beaches on the North Fork, conveniently located near all the best wineries Long Island has to offer! br Read More

    4 Bed
    2 Baths
    Sleeps 8
    $385 / Nightly
  • Property-10 Image 1
    Wonderful
    (27)
    Private Vacation Home
    Beach Front in Southold; newly renovated/baths/kitchen/2nd floor family room!
    Southold, New York, United States

    Newly renovated with two full bathrooms, kitchen and second floor entertainment/family/ bedroom with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! Located on a grassy bluff overlooking the Long Island Sound the house is available for weekly and monthly rentals. Right on the water with its own private beach the beach house has three bedrooms on the ground floor, two with Queen beds, one with a King bed. There is an open plan sitting room with twin beds and picture windows overlooking the water on the second floor. There are two newly renovated full baths; a large living room with fireplace and wall of windows overlooking the Long Island Sound; 42 inch flat screen TV and broad band internet with WiFi; fully equipped newly renovated kitchen with gas stove, counter top dining; dining area with table for 8; adjoining deck also with dining table, and garden, all overlooking the water and spectacular sunsets. The cottage comes complete with linens, beach and bathroom towels, beach chairs, and a laundry room with a washer, dryer. It is also centrally air conditioned and fully winterized. brbrThe cottage comes complete with linens, beach and bathroom towels, beach chairs, loungers and umbrella, and laundry room with a washer, dryer. It is also centrally air conditioned and fully winterized. The property is managed by the Shorecrest Bed and Breakfast and access to Shorecrest’s other water front beach and mooring on the Ashamamocque Inlet, to the rear of the Inn, perfect for kayaking, water-skiing or windsurfing can also be made available to Beach House guests as are concierge services such as restaurant reservations and suggestions, guide books and local event calendars and complimentary wine tastings at local vineyards.brbrRegarding Short Term minimum rental laws in the Town of Southold:brThe Town requires a minimum stay of 14 nights. We can accept a rental for shorter periods of time but we cannot create another separate reservation within the same 14 night period. Therefore in the case that we accept a shorter stay we will block out the unused nights and only charge for those being occupied. There may be an up-charge for a shorter stay, but we offer discounts on a stay of 14 nights or longer for off season bookings.brPlease feel free to contact us with any questions.br Read More

    4 Bed
    3 Baths
    Sleeps 10
    $742 / Nightly
  • Property-11 Image 1
    (60)
    Private Vacation Home
    Located in the heart of wine country/BEACHES/shops.
    Southold, New York, United States

    Historical home full of charm. A home built in the 1700's this home maintains the historical feel with all the amenities of today. This well appointed home is perfect for a relaxing vacation. 3 bedrooms, 2 living rooms, finished sunroom which leads to an english patio and acre of fenced in property. Across the street from a creek, yards from boat ramp and a block away from a private beach. A nice walk into town and a short drive to the wineries.brbrRegarding Short Term Rental Laws: The Town of Southold recently passed legislation requiring a minimum stay of 14 nights in private homes. We can rent for shorter periods of time but we cannot create another separate reservation within the same 14 night period. Therefore in the case that we accept a shorter stay we will block out the unused nights and only charge for those being occupied.brbrSleeps 8brbrCheck-in time 4pmbrCheck-out 11ambrbrPlease contact Carrie if you would like to arrange for a different check-in or check-out time. Check in/out changes must be requested at least 3 weeks before check-in. Read More

    3 Bed
    3 Baths
    Sleeps 8
    $450 / Nightly
  • Property-12 Image 1
    Exceptional
    (3)
    Private Vacation Home
    Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
    Southold, New York, United States

    My home is a hidden gem tucked away in a beautiful and quiet neighborhood in Southold, NY. With beautiful water views and just a few mins walk from the beach, it is a perfect summer vacation rental! The fire place and the North Fork's abundance of vineyards, farms and breweries make this a perfect winter escape as well. Just 2 hours outside of NYC! brbrMessage me if you have questions about the nightly minimum or are wondering about a specific set of dates!brbrMy favorite kind of renters: brbrWe love sharing our home with families, couples and small groups. Our quiet neighborhood is NOT good for events or parties - we love and respect our neighbors! brbrThe Details: brbrThe home is equipped with 3 bedrooms, 2.5 baths. Master has a king bed, second guest room as a queen bed, and the third has 4 single beds. The love seat downstairs pulls out to add an additional twin bed downstairs. The house sleeps 8 upstairs and can accommodate another 2 downstairs between the couch and pullout. Great for families and couples! brbrChefs Kitchen! brbrCentralized Heat and 2 zone AC! brbrWasher/Dryer- in basement, feel free to use if needed (there is detergent to the right hand side). brbrLinens and Towels: there are lots of beach and bath towels in the Master bathroom closet as well as under twin beds in the guest bedroom. Also in the guest bedroom with the twin beds, you will find an extra twin bed frame and mattress with sheets, pillows and blankets. brbrWindows: most have screens so feel free to open or keep closed, whatever you prefer.brbrCushions : for deck furniture are in brown box on deck. brbrWifi: network is available! Will send details once booked in a house guide!brbrTV: Chromecast, Netflix and Amazon Video available! Note - no Cable TVbrbrGarbage: There are two cans in the garage. Please place garbage in the left hand can (the one with trash liner) at the end of weekend. Recycling goes in the right hand garbage can. brbrSpot Cleaner: there’s a heavy duty spot cleaner under the sink in the kitchen in case of any spills brbrBikes: Feel free to use! There are 7 in the garage. brbrGrill - Charcoal bbq (might need to pick up more charcoal at the IGA in town) or Smoker downstairs in the garage! brbrThe good stuff: brGood recent Eater write up: that covers a lot of the popular spots click here. brMap of our favorite places: brbrMap of area beaches: brbrNorth Fork is very special place. On the “favorite places” map I will send you is the location of the private association beach which is a small but beautiful spot and is a nice walk or bike ride from the house. brbrThe “best of the best” list: brBest vibe dinner: American Beech, Noahs brBest casual dinner: Lucharitos (tacos and queso!) brBest Pizza: 1943 brBest Cocktails: Brix and RyebrBest new local spot: Port in Greenport (owners also own a fantastic restaurant in Shelter Island called Salt) brBest beer: Greenport Brewery (Peconic- not greenport town)brBest burger: Greenport Brewery (Peconic- not greenport town)brBest “fancy” dinner: North Fork Table & InnbrBest Beach & Best Sunset: Sunset Beach on Shelter Island - you can take a cab or drive there via the ferry in GreenPort brBest Rose: Corey Creek / Bedelle, Bridge Lane brBest Vineyard Setting: Croteaux (but the owner doesn’t allow parties greater than 6)brBest White: Kon-to-kosta brVineyard with most outdoor activities: Ospery’s Dominion brbrbrbrbr Read More

    3 Bed
    3 Baths
    Sleeps 6
    $529 / Nightly
  • Property-13 Image 1
    Excellent
    (6)
    Private Vacation Home
    Gite de L'entente - Macey
    MACEY, TROYES ET SES ENVIRONS, France

    pSituated in a rural area, this welcoming vacation home brings all of Macey within your reach. You'll easily make the 11-minute drive to Seine or the 14-minute drive to Centre de Congrès de l’Aube. /ppYou can make the most of the outdoors with the garden and BBQ grill at this 1259-sq-ft vacation home. As for the great indoors, you can come inside and enjoy the free WiFi and TV. /ppThe kitchen is equipped with a dishwasher, a microwave, and a toaster. And you won't have to pack extra clothes, because you'll also have a washing machine. /p Read More

    3 Bed
    2 Baths
    Sleeps 6
    $103 / Nightly
  • Property-14 Image 1
    (9)
    Private Vacation Home
    Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries
    Southold, New York, United States

    Make yourself at home in this two bed, two bath home in the heart of North Fork Wine Country! One bedroom has a queen bed with walk-in closet and sliding glass doors that lead to the deck in the quiet and private backyard. The second bedroom has a full size bed. The living room is equipped with a queen size pull out couch. Plenty of room for up to six people! There are two full bathrooms and a fully equipped kitchen. The backyard has a deck with lounge chairs, patio table and chairs, grill and bar. There is also a fire pit perfect for roasting marshmallows. Enjoy a game of cornhole on the property! There is plenty of outdoor seating including Adirondack chairs for around the fire. The home is conveniently located within walking distance to Kenney’s Beach. Included with the rental are beach chairs, floats and a beach wagon. There are several vineyards within walking distance as well. brEnjoy a short trip to Greenport for shopping and dining along the harbor side. This property is easily accessible to Shelter Island. brThis home has a lot to offer you for a lovely vacation.brbrIf you would like a beach pass there will an additional $40 fee. A license plate number and name on registration is required. brbrCheck In Time: 1:00 PMbrCheck Out Time: 11:00 AM Read More

    2 Bed
    2 Baths
    Sleeps 6
    $550 / Nightly
  • Property-15 Image 1
    Exceptional
    (4)
    Private Vacation Home
    Newly Renovated Gem on the Cedar Beach Peninsula!
    Southold, New York, United States

    Come and experience the peaceful tranquility of the North Fork with this newly renovated gem in the heart of Southold. Ideally located a short walk to either Goose Creek Beach or Cedar Beach and right up the road from Croteau Vineyards and the North Fork wine trail. brbrThe house is situated on shy acre bordering preserved farmland. Enjoy a backyard BBQ on the stone patio which features a grill, an eight-person dining set, lounge chairs and firepit. If you would like to enjoy the backyard beyond a delicious meal or a cocktail, there is basketball, bocce ball, croquet and cornhole. The front stone patio boasts a bistro set surrounded by beautiful flowers and landscaping which makes a perfect setting to enjoy your morning coffee. brbrThe first-floor of our home offers an open kitchen/dining room which can sit up to 9 people for a family meal. The kitchen is fully equipped with a refrigerator (water & ice), stove/oven, microwave, dishwasher, Keurig coffee/cappuccino/latte maker, blender, and toaster. There are plenty of cooking utensils, pots, pans and of course a variety of spices. It is a perfect place to enjoy a true North Fork farm to table experience. The living room is equipped with a recliner, reclining sofa, electric fireplace, ceiling fan, PlayStation 3 and a 75” Smart TV. There is also a powder room and full laundry on the first floor.brbrThe second-floor features 4 large bedrooms themed to celebrate the beauty of the North Fork each with their own full bath en-suite. Each bedroom has its own work station and Smart TV. The second-floor landing area has been designed as a space for you to enjoy a good book or a place to just relax and enjoy the view of the sunset. Read More

    4 Bed
    5 Baths
    Sleeps 10
    $883 / Nightly
  • Property-16 Image 1
    Exceptional
    (1)
    Private Vacation Home
    Waterfront Retreat Easy Walk to Pristine Beaches & Near Wineries
    Southold, New York, United States

    Waterfront retreat in quiet, tree lined neighborhood. Enjoy Summer days out on the spacious wrap-around deck, go upsstairs to roof deck or relax inside in the sun drenched open living area with high ceilings and sky lights. Cook up a delicious meal in the spacious, fully equipped kitchen with breakfast nook and bar-style seating, or have a sit-down dinner at the dining table. First floor has 2 bedrooms with one queen and one twin singles and a full bath. Upstairs features an open loft area as well as a master suite with full bath including jacuzzi and shower. Read More

    3 Bed
    2 Baths
    Sleeps 6
    $300 / Nightly
  • Property-17 Image 1
    Exceptional
    (1)
    Private Vacation Home
    Charming English Tudor
    Southold, New York, United States

    This spacious and charming 4,500 square foot English Tudor is situated on 2.25 acres in Southold. It has 4 bedrooms, 3 bathrooms, laundry room, high-end kitchen, living room, den and full gym in the basement. The rustic entryway leads to a living room with a massive stone fireplace and 'Disappearing' wall - bringing the outside in. The kitchen has a Wolf gas stove, sub zero refrigerator, a separate sub zero freezer, plenty of dish-ware and a cozy breakfast area that is also suitable for casual dining. Just off of the kitchen is the formal dining room with a private terrace with mature vines covering the pergola. The master suite is located on the second floor and has it’s own private roof terrace overlooking the mature landscaping and open fields. Just across the walkway overlooking the living room there is 2 additional bedrooms and a full bathroom. brThe house is 18 minutes from the Cross Sound Ferry and roughly 2 hours from the city. Town Beach is less then 2 minutes down the road and across the street is One Woman Wines. Greenport Village is a short 4 miles away and there you can enjoy the many restaurants and small shops. Let the kids have a carousel ride or two then take a walk along the docks. The North Fork offers many cute and quaint villages to explore, spend the day at the beach, wine tasting or antiquing, then come back and enjoy the calming and peacefulness of your surroundings. Read More

    4 Bed
    3 Baths
    Sleeps 10
    $1,500 / Nightly
  • Property-18 Image 1
    Exceptional
    (6)
    Private Vacation Home
    Luxury by the Sea
    Southold, New York, United States

    Your search ? is over! Brand New ? Construction. Charming, luxurious, private, comfortable Beach ? House. Stunning 3 bedroom 21/2 bath house on fully fenced in 1.25 lush acres. br King size master ? with gorgeous en-suite has separate soaking tub ? and spa shower?. This home is beautifully designed with too many architectural details to list with amazing detail and craftsmanship. br Property is fully furnished ? with no detail spared . Open floor plan, spacious great room with gas remote controlled fire place and flat screen, and gourmet eat ? in kitchen with large island is a wonderful place to entertain ?. br Brand new washer/dryer, butlers pantry and mud room. Attached 1 1/2 car ? garage with plenty of storage. Plenty of parking. br Where the country meets the sea ? enjoy all the North Fork ? has to offer. You’re in the middle of beach and Wine Country with tons of vineyards ? and local farms to explore. Beautiful beaches are 2 min away in any direction. br Close to the Tanger outlets and so many other shops in beautiful Riverhead as well as the ? Aquarium. You can also take a 10 min drive to beautiful Greenport or hop on the ferry to Shelter ? Island. br So much to do or just stay home relax ? and enjoy the beautiful tranquil patio, new Weber BBQ ? with its own gas?? line and beautifully landscaped ? enclosed yard. br You will not be disappointed. All beach gear, 4 beach chairs, 2 ? coolers, beach umbrellas ?, wagon etc are included with your stay!!br The only thing missing is YOU…??br Read More

    3 Bed
    3 Baths
    Sleeps 8
    $405 / Nightly
  • Property-19 Image 1
    Private Vacation Home
    Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit
    Southold, New York, United States

    Southold SerenitybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrSummer by the water awaits when you book this lovely, three-bedroom Southold home, with a gorgeous, enormous lawn and private pool. Surrounded by trees and greenery, you’ll feel a million miles away from it all, yet you’re minutes from North Fork attractions. Start the day outside on the patio, sipping coffee or taking a dip in the pool. Play a game of corn hole or life-sized Jenga, and, when hunger strikes, head inside to the well-equipped kitchen to make breakfast. Eat together at the adjacent dining table, or step back outside and dine alfresco. brbrSpend the day exploring the area’s beaches, farm stands, wineries, and small towns, and return to relax by the pool. In the evening, grab a seat on the comfy couch and stream the latest release, upload the day’s pics to social media with the free WiFi, or engage in quiet conversation in the formal living room. Call it a night in one of three comfortable bedrooms - another perfect water day awaits tomorrow. brbrTHINGS TO KNOWbrStreaming services are available with guest accounts.brA queen sofa bed provides extra sleeping space.brNo smoking is allowed in this home.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.brbrCity/town permit number: 0689 Read More

    3 Bed
    3 Baths
    Sleeps 8
    $398 / Nightly
  • Property-20 Image 1
    Very Good
    (6)
    Private Vacation Home
    Waterfront with dock on Goose Creek (just off Peconic Bay) and chef's kitchen
    Southold, New York, United States

    Idyllic North Fork Rental on Goose Creek with Private Dock and Breathtaking Sunset Views. Features Gourmet Chef's Kitchen, First Floor MBR En Suite and Two Additional Bedrooms and Bath on 2nd Floor. House is recently renovated with luxury furniture, peloton bike and well-appointed rooms. Must see to appreciate this well-located house perfect for a seasonal retreat. Just minutes to local wineries, farms, restaurants and nature trails. Go paddle-boarding, kayaking or boating right off your rear porch! Read More

    3 Bed
    3 Baths
    Sleeps 6
    $849 / Nightly
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Most popular vacation rentals in Southold

  • thumb
    $ 526.00 avg/night
    2
    • 4 Beds
    • 2 Baths
    • 8 Guest(s)
    Idyllic waterfront home with dock, kayaks, bikes, firepit, & fireplace - dogs OK Southold, New York, United States

    Come Sail AwayOur calendar is updated in real-time & our nightly rates are accurately displayed.... Read More

  • thumb
    $ 699.00 avg/night
    2
    • 4 Beds
    • 2 Baths
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    Southold Sanctuary - North Fork Getaway Southold, New York, United States

    Book your getaway now to the beautiful North Fork of Long Island. This newly renovated 4 bedroom,... Read More

  • thumb
    $ 529.00 avg/night
    3
    • 3 Beds
    • 3 Baths
    • 6 Guest(s)
    Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8 Southold, New York, United States

    My home is a hidden gem tucked away in a beautiful and quiet neighborhood in Southold, NY. With... Read More

  • thumb
    $ 356.00 avg/night
    18
    • 4 Beds
    • 4 Baths
    • 8 Guest(s)
    Waterfront, New Construction North Fork Beach House Southold, New York, United States

    Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This... Read More

  • thumb
    $ 180.00 avg/night
    3
    • 3 Beds
    • 4 Baths
    • 6 Guest(s)
    A Natural Getaway Southold, New York, United States

    This lovely stroll-to-the beach "farmhouse," built in 2019 on a woodsy acre, is bright, peaceful... Read More

  • thumb
    $ 200.00 avg/night
    1
    • 2 Beds
    • 2 Baths
    • 4 Guest(s)
    Cottage on private road and 5-min walk to beach Southold, New York, United States

    Perfect all-season cottage with easy access to beaches, wineries, restaurants, and all the great... Read More

  • thumb
    $ 1010.00 avg/night
    3
    • 8 Beds
    • 7 Baths
    • 12 Guest(s)
    New Modern Farmhouse Estate Living in the heart of Southold with a pool!!! Southold, New York, United States

    A beautiful brand new estate home with a heated pool, situated in the heart of picturesque North... Read More

  • thumb
    $ 340.00 avg/night
    1
    • 5 Beds
    • 4 Baths
    • 12 Guest(s)
    Sprawling waterfront home with bikes, kayaks, pool table, and grill - dogs ok Southold, New York, United States

    The North Fork Beach HouseOur calendar is updated in real-time & our nightly rates are accurately... Read More

  • thumb
    $ 548.00 avg/night
    17
    • 4 Beds
    • 3 Baths
    • 10 Guest(s)
    Waterfront, private beach, ready for adventure, light & bright! Southold, New York, United States

    Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water... Read More

  • thumb
    $ 405.00 avg/night
    6
    • 3 Beds
    • 3 Baths
    • 8 Guest(s)
    Luxury by the Sea Southold, New York, United States

    Your search ? is over! Brand New ? Construction. Charming, luxurious, private, comfortable... Read More

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