Vacation Rentals By Owner In Southold, NY

Showing 20 Of 139 Vacation Rentals

$859.9

Charming Southold Waterfront Property

Southold, New York, United States

Welcome to our beautiful waterfront home with breathtaking views of Hashamomuck Pond—an idyllic setting for an unforgettable family vacation. Immerse yourself in the charm of the North Fork, with nearby beaches, wine country, farm stands, and top-rated restaurants.brbrThis spacious home features 3 bedrooms and 2 full baths. On the first floor, you'll find a master bedroom, a guest room, and a bonus room with a pull-out couch. The second floor offers another guest room with two queen beds, perfect for additional guests.brbrMake the most of your stay with amenities like a BBQ, paddle boards, kayaks, a fire pit, and plenty of outdoor seating to relax and soak in the stunning surroundings.

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$1152.84

/ Nightly

Private Vacation Home

Discover the Perfect Northfork Home

Southold, New York, United States

Discover the best of Southold in this sophisticated 4-bedroom, 3.5-bath home, ideally situated close to Town Beach & Kenney’s Beach. Located near some of the region’s most famous vineyards, this home provides a peaceful retreat with easy access to the area’s top attractions.brbrOffering a perfect mix of luxury, comfort, and convenience, this Southold gem is ready to welcome you. Book your stay today and enjoy all the beauty and charm that the Northfork has to offer!

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$456.19

/ Nightly

Private Vacation Home

Family Beach House on the North Fork of Long Island

Southold, New York, United States

Welcome to our Family Beach House, nestled on the coast of the Peconic Bay in the charming town of Southold, New York. Embrace the tranquil beauty of the North Fork, enjoy the many vineyards and create cherished memories in our serene seaside retreatbrbrPermit #0502brMinimum 2 week stay - please reach out for customization

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Exceptional(4)

$408.14

/ Nightly

Private Vacation Home

Salt & Sea House - beaches, wineries, farms nearby

Southold, New York, United States

Escape to the Salt & Sea House!brbrEmbrace the tranquility of our spacious 3 bedroom, 3 bathroom home nestled on a private 3/4 acre wooded lot. Unwind under the stars with a glass of wine or cozy up on the couch with a good book and the soothing sounds of jazz.brbrOur fully equipped kitchen is a chef's dream, complete with everything you need to create delicious farm-to-table meals.brbrNeed to work remotely We've got you covered with a dedicated workspace featuring a Herman Miller chair, standing desk, monitor, Apple keyboard and mouse, and an HDMI cable for your MacBook (just bring your laptop!).brbrAfter a productive day, explore the nearby orchards and treat yourself to a refreshing cider. At the Salt & Sea House, you can seamlessly blend work and relaxation.

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Exceptional(3)

Select Dates for Price

Private Vacation Home

A Natural Getaway

Southold, New York, United States

Welcome to a family-fun, pet-friendly house (Rental permit 0343) built in 2019 on a woodsy acre-plus. The home is a stroll to a beautiful Long Island Sound beach and centrally-located, with 3-bedrooms, 2.5 baths, an office and a TV den. Enjoy the outdoor shower, pebbled patio and yard. The property is a 7-minute stroll to pristine McCabes Beach, and 2 miles to Southold village where the Hampton Jitney stops to-and-from Manhattan. A 10-minute drive leads to trendy Greenport where 2 short ferry-rides head to The Hamptons.

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$1780.89

/ Nightly

Private Vacation Home

Well-appointed coastal home with large yard, pool, basketball, & outdoor kitchen

Southold, New York, United States

Secret Garden EstatebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCharm flows freely throughout this lovely Southold property. Indulge in a luxury coastal vacation and spend your days enjoying the sun while surrounded by fresh blooms, turquoise waters, and your favorite people. An ideal place to entertain, the expansive backyard boasts yard games, a pool, water-side loungers and umbrellas, a basketball court, and a fully equipped outdoor kitchen. When you aren't hanging out here, head inside. Just as beautiful as the outdoor space, the interior displays comfortable furnishings, vaulted ceilings, and carefully curated decorations. brbrThe airy living room has ample seating, a large Smart TV, and a grand piano. Steps from here, the chef's kitchen positively shines with its stainless steel appliances and gleaming countertops. When your culinary creations are ready to be indulged, gather around the expansive formal dining table inside, or host a garden party and dine al fresco. brbrEqually inviting, the four bedrooms are places of pure peace. Soft linens, central air, and natural lighting compose each. The little ones of the family are catered to with their room featuring toys, cribs, and a Pack-N-Play. The home's bathrooms are equally impressive with perks like walk-in showers and large vanities. Perks like a laundry room, central air-conditioning, and a fireplace round out the interior amenities. brbrWhen you can pull yourself away from your whimsical retreat, visit Founders Landing Park, Town Beach, Orient Beach State Park, and the area's numerous wineries, restaurants, and local shops. brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 6 vehicles.brbrSecurity camera details: At the front entry and back entry door, facing outwardbrbrbrbrDamage 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.

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Exceptional(30)

$367.66

/ Nightly

Private Vacation Home

North Beach Fork Beach House

Southold, New York, United States

Enjoy our tranquil home in a private beach community.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 .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.

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$1151.42

/ Nightly

Cottage

North Fork Waterfront Spectacular Views Cottage circa 1930

Southold, New York, United States

North Fork Waterfront Spectacular Views Cottage circa 1930'brOn Golden Pond' Private road, amazing waterfront view, 100+' water front, shallow calm water, great for kids, look at the photos. Row boat and canoe at the waters edge for your use. Walk to the public beach across the street on the Long Island Sound or swim in front of the house in the tidal salt water lake that connects to the Peconic Bay!

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Exceptional(24)

$349.98

/ Nightly

Cottage

Lovely 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.

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$1144.87

/ Nightly

Private Vacation Home

Waterfront property with own dock and stunning views, overlooking Southold Bay.

Southold, New York, United States

Welcome to our home, a one of a kind Bayfront property with a private dock, a large, expansive deck, overlooking Southold Bay, with views to Shelter Island. Only a short distance from charming Southold Town and a variety of beautiful Bay-side and Sound-side beaches. brImmerse yourself in the beauty and tranquility of the North Fork by staying at our charming, waterfront home.brbrOur property has a very unique setting on a sought-after road in Southold. Its look and layout ensure it stands out in the area. It sits on Jockey Creek, with dazzling views over Southold Bay and Shelter Island beyond.brbrThe large, comfortable deck offers a safe haven from the hustle and bustle of nearby Southold and Greenport. It’s a place to relax and enjoy the views, with plenty of outdoor furniture and a gas BBQ, perfect for those lovely summer evenings.brbrWith its own dock, you can enjoy kayaking around the Bay Area - Jockey creek and other nearby waterways. It is fun to explore the nearby Bayside beaches - Goose Creek beach and Founders Landing with beach passes we can provide.brbrFishing from the dock is the perfect way to start or finish your day in the North Fork. We have rods that you can use. Even clamming, with the correct license, can be done on the nearby sandbars and areas, accessed by kayak.brIf you have access to your own boat, you are able to travel to the house and dock there. Some fabulous restaurants are accessible in Southold, Greenport and on Shelter Island by boat.brbrSouthold Town is half a mile away - a short walk or easy cycle ride. It’s a quaint village with some must-try restaurants and fabulous home decor shops and other boutiques.brbrThere is access to tennis courts, running track and a basketball court at nearby Southold school.brbrWe have several bicycles for those who would like to soak up the nearby countryside, ride to the Sound or Bay side beaches and visit the delightful wineries in the area. They are a real treat!

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Exceptional(6)

$799.75

/ Nightly

Private Vacation Home

Secluded charmer with gunnite & saltwater pool, stone fireplace steps to beach!

Southold, New York, United States

Built in 1928, this gorgeous shingled home is fully equipped to host your getaway. You're within easy walking distance of Horton's Lighthouse, where lovely beach walks and stunning sunsets await you. The famous local wineries are all within short drives of this lovely retreat. Enjoy staying in a classic home with stone accents throughout, as well as lovely additional amenities like a new heated gunnite pool with plenty of poolside seating. A new central AC system will keep the indoors cool and comfortable while you're resting from swim. The high speed WiFi will help you complete your assignments at the desk workspace. Enjoy putting meals together in the newly renovated kitchen, or fire up the gas grill for a home grilled meal. The family friendly layout features plenty of seating inside and out. You're just 100 yards north of a public beach, come enjoy the sunsets!

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Exceptional(1)

$464.02

/ Nightly

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.

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Exceptional(1)

$592.71

/ Nightly

Private Vacation Home

North Fork Dream Getaway, Walk to Private Beach & In-Ground Pool!

Southold, New York, United States

Escape to paradise with this stunning north fork home, where relaxation and adventure meet! A quick walk to the beach, this beautifully designed 3-bedroom, 2-bathroom retreat is the ultimate getaway for families or groups seeking a beachside escape with updated amenities and plenty of space. Serene backyard includes large outdoor dining, fire pit and pool. This property offers a combination of tranquility and excitement. Get ready to explore all of what Southold has to offer!brbrKey Features:brBeach Location: 5 minute walk to beach with private access. Wagon, beach chairs, umbrellas, coolers, kayaks & lifejackets available. brbrUpdated Kitchen & Living Space: Living room features wood burning fire h place, large screened in porch with dining, cozy TV room with pull-out queen couch. Semi open floor plan with great entertaining flow. brbrGourmet Kitchen: Fully equipped with high-end appliances, sleek countertops, and all the cookware you'll need to prepare gourmet meals. Large island with seating for 8. Gas grill with propane. brbrSpacious Bedrooms: Master suite hosts a king-sized bed, with en-suite bathroom. Additional bedrooms sleep 2 adults, each. brbrEntertainment: High-speed Wi-Fi, TVs in main living areas. Bikes for adults and children. brbrOutdoor Oasis: The oversized deck is perfect for dining al fresco or lounging with friends and family by large pool. The property also includes a fire pit for those cozy evening gatherings.brbrIdeal Location: Located in a quiet, upscale neighborhood, perfect for those who want to escape the hustle and bustle while being close to everything the north fork has to offer. Local wineries, breweries, restaurants, shopping, and attractions. Enjoy the best of both worlds – peaceful beach days and easy access to nearby activities.brbrBook Your Stay Today!brbrThis beach house is the perfect place to unwind and create lasting memories. Don’t miss out on your chance to stay at this North Fork dream getaway! Here is a link for a video walkthrough : https://youtu.be/nQPoGqOaQ3M

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Select Dates for Price

Private Vacation Home

Beautiful private home with beach access down the block

Southold, New York, United States

1/2 acre fenced property. open floor plan. Master with en suite bathroom. additional bedrooms and bathrooms for your use. Backyard is spacious, with a volletball net, outdoor shower, grilling area, and firepit.

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Exceptional(23)

$610.33

/ Nightly

Private Vacation Home

Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries

Southold, New York, United States

Southold Permit # 0361. Pool opens Mid April! One season off of a full renovation - reviews before 2022 are from before our renovation -- Fully renovated North Fork ranch home with gorgeous heated pool, huge yard and ipe deck overlooking Goose Creek. Perfect for an East End getaway for the summer months, or in the off season. Our home sits on a half acre landscaped property overlooking Goose Creek. Kayak or stand up paddle board from our private dock or take a short walk/drive down to the South Harbor Park beach or Cedar Beach. We are also within walking distance to Croteaux vineyards, the only Rose-only winery on the North Fork. brbrNeed to work remotely We have an office/den with desk space, office supplies, and exercise area with Peloton in the basement.brbrOur house is super comfortable and easy to manage with a family or a couple other friends. You will have access to private heated pool and private dock - perfect for using our kayaks (2), paddle boards (2). House has 3 Bedrooms and 2 full baths with additional half bath and outdoor shower. The office/den also has a queen sofa bed. Full kitchen with new appliances, dining area - seats 10 (8 comfortably), outdoor dining and seating area, large deck, living room, washer/dryer, air conditioning, 3 cable TVs and WiFi. brbrWe are centrally located in a quiet neighborhood, seconds from wineries, farm stands, restaurants and a short drive into Southold Town. Just down the street, and in walking distance, is Croteaux vineyards - perfect for winetasting and not having to drive! We are also a short drive from Bedell, McCall and Sparkling Pointe vineyards. Greenport Harbor Brewery in Peconic is an easy 5 minute drive. brbrOur house is perfect for families and friends looking for an easy, comfortable, accessible, and most importantly, relaxing get-away in the beautiful North Fork. brbrThe details: 3 Bedrooms- Master bed with private full bath with King sized bed, 3 guestrooms with queen sized beds, 1 guest full bath and 1 half bath. Large living room, with L shaped couch and connection to dining area. Large outdoor space with retractable awning covering outdoor dining table and outdoor gas grill. brbrIdeally looking for monthly or multi-week rental tenants. Please feel free to contact us to discuss the terms of your vacation length.

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Exceptional(2)

$1249.06

/ Nightly

Private Vacation Home

Sandy Bay Beach

Stunning waterfront location with amazing sugar sand beach!brbrWell proportioned home with beautiful symmetry. The central fireplace and chimney and beautiful roof lines are the main architectural feature. Built in are the living room with sliders to covered porch, kitchen, dining room, entry foyer and full bath make up the main level. Three bedrooms and a full bath with deep soaking tub and rainshoweron the second floor! Private outside shower!brbrOur tenants often say they do experience a peaceful feeling of nostalgia and happiness that many refer to as soul soothing, healing and magical at our location. The house is an updated traditional summer house from a by-gone era situated on the southern shore of this waterfront peninsula directly on Southold Bay with spectacular views from this wonderful location. brbrKick off your shoes, grab a book and relax on the bay-side porch or spend your day at the spectacular sandy beach just steps away!

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$979.28

/ Nightly

Private Vacation Home

Stylish beach getaway: pool in prime location

Southold, New York, United States

Welcome to our beautifully renovated, designer-decorated home in the heart of Southold, NY! Perfectly located within walking distance to charming shops, pristine beaches, and the town's best restaurants, our home offers the ultimate blend of luxury and convenience.brbr- Prime Location: Enjoy easy access to everything Southold has to offer.br- Private Pool: Unwind and soak up the sun in your own private pool.br- Modern Renovations: Recently renovated to perfection with stylish designer touches throughout.br- Spacious Living: Three beautifully decorated bedrooms and two modern bathrooms.br- Work-Friendly Space: Dedicated workspace with high-speed Wi-Fi for remote working.brbrBedrooms br- Primary Suite: Relax in the luxurious master bedroom with a plush king-size bed.br- Guest Bedroom: A second bedroom featuring a comfortable queen-size bed.br- Kids' Room: A fun and cozy room with bunk beds, perfect for kids or extra guests.brbrBathrooms: br- Two modern bathrooms featuring high-end fixtures, steam showers and Bathing Culture amenities.brbrLiving & Dining:br- **Open-Concept Living:** The bright and airy living space, adorned with chic decor, is perfect for relaxing or entertaining. Comfortable seating and a smart TV make it an ideal spot to unwind after a day of exploring Southold.br- Gourmet Kitchen: The fully equipped kitchen boasts top-of-the-line appliances and all the essentials you need for preparing meals. Whether you're whipping up a quick breakfast or a gourmet dinner, you'll find everything you need here.br- Dining Area: The elegant dining area, with seating for eight, provides a stylish setting for family meals or dinner parties. Enjoy your culinary creations in a beautiful and comfortable space.brbrOutdoor Space:br- Private Pool: Step outside to your private oasis. The sparkling pool is perfect for cooling off on warm days, and the surrounding lounge chairs invite you to soak up the sun. An outdoor dining area lets you enjoy meals al fresco.br- Garden: The beautifully landscaped garden offers a serene retreat. It's an ideal spot for morning coffee or evening relaxation, surrounded by lush greenery.brbrWe look forward to hosting you, feel free to reach out with any questions!

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$330.78

/ Nightly

Cottage

House central to North Fork wineries restaurants + beaches. Walk to town.

Southold, New York, United States

Comfortable House on a quiet private road 0.5 mile to Southold town center. Would work well for a small family or two couples for a maximum of four people. Two bedroom two bathrooms with central AC . Fully equipped kitchen with large dinning table. Parking for two cars in the driveway. Large garden with bbq, a spacious deck for lounging, reading and catching the sun. Central to many North Fork wineries, local beaches and restaurants. A peaceful retreat to decompress within walking distance (0.5 mile) to LIRR and Jitney from NYC. Founders Landing bay beach within one mile, Kenny’s beach (on the sound) 2.5 miles from the house. Historic Greenport is a 10 min drive.

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$994.65

/ Nightly

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.

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Exceptional(3)

$1586.72

/ Nightly

Private Vacation Home

NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!

Southold, New York, United States

Make yourself at home in this spacious and beautiful North Fork Wine Country home in the heart of Southold! This 4,000 sq. ft. home comfortably sleeps eight adults in and boasts a chef's kitchen, 4 spacious bedrooms, 3.5 bathrooms, a gorgeous screened-in sunroom with big screen TV, large couch and chairs. This beautiful home has two master king suites each with ensuite baths and walk in closets. Ultra-high ceilings, large sunny windows and spacious open layouts throughout. Spectacular 40x20 heated pool with a slate patio, sun ledge, and waterfall. Full size deck with dining and sitting area. Resort living with a hot tub, steam shower, and jacuzzi. Perfect for large families, groups, and entertaining. Bike to the beach in less than 1.5 miles. Includes kayaks, paddle boards and bikes for families. Sleeps 8 adults in beds! Each room in the house is equipped with a mounted flat screen TV.br brThe kitchen and dining area have a view of the deck that overlooks the fully fenced-in backyard with the pool. Relax in the living room or family room or respond to some emails in the cozy home office. The deck has ample seating with dining table and lounge chairs to enjoy the pool while cooking up some burgers on the grill and winding down for the night on the patio or roasting marshmallows on the fire pit. br brFeaturing: large fenced in yard, pool, fire pit, grill. Fireplace, central climate control, Fisher and Pishkal stove top, 8+ smart tvs, dishwasher, washer & dryer. Nest/Ecobee climate control from smartphonebr brIf you are interested in a private getaway that far exceeds other listings just contact us and we can work together planning your getaway! Last minute listing, priced to move and won’t last. Available YEAR ROUND and pool remains above 80 through October!br brThe North Fork has plenty of beautiful sights and activities for you to enjoy. Walk down the road to The Old Field Vineyard for a wine tasting, hop in the car and head to the Village of Greenport (about 4 miles away) to enjoy their many restaurants and boutiques along the harbor. Plan a trip to Shelter Island, Sag Harbor, and the Hamptons via the North and South Ferries! There are plenty of nearby North Fork beaches along either the Long Island Sound or Peconic Bay to enjoy.his home is a perfect spot for a relaxing, dreamy, North Fork escape! Just a short drive away from some of the best vineyards on the North Fork, the famous Love Lane, Beaches on the Long Island Sound as well as Peconic Bay. You will never be bored. There is plenty of shopping in Southold, Mattituck, Greenport Town and Tanger Outlets in Riverhead with countless little shops filling the space between.brbrDISCOUNTS AVAILABLE. PLEASE INQUIRE. SOUTHOLD REQUIRES TWO WEEK MINbrbrRental ID: 78-1-38 / 1197

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Rent a place that suits your needs

Private vacation home

View 100 Private vacation home

Most popular vacation rentals in Southold

Exceptional(3)

$1586.72

/ Nightly

Private vacation home

NORTH FORK DREAM HOME, 4,000 Sq Ft, 1 Acre, Heated Pool!

Southold, New York, United States

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Exceptional(3)

$411.57

/ Nightly

Cottage

SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS

Southold, New York, United States

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Exceptional(3)

$408.14

/ Nightly

Private vacation home

Salt & Sea House - beaches, wineries, farms nearby

Southold, New York, United States

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Bath

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Exceptional(3)

$872.63

/ Nightly

Private vacation home

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold, New York, United States

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Exceptional(3)

$839.14

/ Nightly

Private vacation home

Bayfront Vacation Home in Southold, 5 Bedrooms

Southold, New York, United States

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Exceptional(3)

$614.29

/ Nightly

Private vacation home

Spacious Waterfront Home with Outstanding Waterviews!

Southold, New York, United States

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Exceptional(3)

$748.34

/ Nightly

Private vacation home

Greenport Walk to beach & vineyard from this brand new home

Southold, New York, United States

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Sleeps

Exceptional(3)

$1577.79

/ Nightly

Private vacation home

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold, New York, United States

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Exceptional(3)

$474.14

/ Nightly

Cottage

Charming Cottage

Southold, New York, United States

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Bath

Sleeps

Exceptional(3)

$777.56

/ Nightly

Agritourism

Cozy Long Island Escape

Southold, New York, United States

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Vacation Rentals By Owner In Southold, NY

$859.9

$1152.84

$456.19

$408.14

$1780.89

$367.66

$1151.42

$349.98

$1144.87

$799.75

$464.02

$592.71

$610.33

$1249.06

$979.28

$330.78

$994.65

$1586.72

Rent a place that suits your needs

Most popular vacation rentals in Southold

$1586.72

$411.57

$408.14

$872.63

$839.14

$614.29

$748.34

$1577.79

$474.14

$777.56

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