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Southold Rentals
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- From $487 per night (USD)
VRBO
Between the Vineyard and Sea on the North Fork. Permit #: 0378
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Private midcentury beach cottage walking distance to Croteaux Vineyard and South Harbor Beach. Completely updated three ...
From $487 per night (USD)VRBO
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Expedia
The perfect north fork experience
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Our home is on a 10 acre private field surrounded by beaches, farms and local wineries. We have a large fenced pool with ...
Click For PricingExpedia
- From $1424 per night (USD)
VRBO
Truly special! Huge North Fork Villa Great for multiple families- Walk to beach
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This stunning luxury home is everything you could possibly want in a vacation rental! -6 Bedrooms -4 Bathrooms -Huge 2 ...
From $1424 per night (USD)VRBO
- From $553 per night (USD)
VRBO
NorthFork Serenity, next to beach and wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A stones throw to your private creek entrance or an 8 minute walk down a private road to the exceptional Goose Creek Bea ...
From $553 per night (USD)VRBO
- From $900 per night (USD)
VRBO
Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the beauty of Long Island's North Fork right here at our vacation house in Southold. Enjoy fabulous water views, ...
From $900 per night (USD)VRBO
- From $445 per night (USD)
VRBO
Southold McCabe's Beach Retreat - Walk to the beach; Relax & enjoy all seasons!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Carefree retreat by the beach: recently renovated, wonderfully furnished. CAC, 3 large bedrooms, 2 full baths, open conc ...
From $445 per night (USD)VRBO
- From $402 per night (USD)
VRBO
2 Bedroom Apartment in Historic Home with private yard (WBH)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Calendar NOT always up to date check for availability Beach Parking good at all Southold Town Beaches Pass INCLUDED fr ...
From $402 per night (USD)VRBO
- From $850 per night (USD)
Expedia
Beachfront - endless sunsets, sandy beach, cozy sunroom & open concept kitchen
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled on the water, this 3-bedroom, 2 1/2 bath house is a bright and open space perfect for creating unforgettable mem ...
From $850 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
One block from the beach!!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Available August - Labor Day 2021!! $30,000.00 Take a long walk on the beach or set sail in Southold Bay for Shelter I ...
From $1000 per night (USD)VRBO
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Expedia
Enjoy Wine Country and Walk The Beautiful Beach At Sunset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
* 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. ...
Click For PricingExpedia
- From $1500 per night (USD)
VRBO
Beautiful waterfront house in Southold
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful Waterfront Home With Stunning Views of Hashamomuck Pond. Escape from it all for a memorable family vacation in ...
From $1500 per night (USD)VRBO
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Expedia
Enjoy Wine Country and Take Walks On Beautiful, Solitary beaches At Sunset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
* 10 min walk to neighborhood sandy beach * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Ma ...
Click For PricingExpedia
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VRBO
New home with open floor plan located close to wineries and Greenport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home located near the water. 4 bedroom, 3 bathroom open floor plan built in 2019. Very close to wineries, Gree ...
Click For PricingVRBO
- From $300 per night (USD)
VRBO
Charming house walking distance from beautiful Kenney’s Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience the North Fork in our bright, happy home in the heart of wine country, just steps from beautiful Kenney's Bea ...
From $300 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Quaint Cottage Close to LI Sound
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
This newly renovated cottage is located in the middle of wine country and close to the Long Island Sound. The property i ...
From $275 per night (USD)VRBO
- From $941 per night (USD)
VRBO
Unique Southold waterfront luxury home with heated pool on Long Creek
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
We bought our wonderful house five years ago and have made many important renovations. The newest is a hybird bocce cour ...
From $941 per night (USD)VRBO
- From $390 per night (USD)
VRBO
Cute Cottage Apartment Near town, beaches and vineyards (WBH)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Calendar NOT always up to date check for availability Beach Parking good at all Southold Town Beaches Pass INCLUDED fr ...
From $390 per night (USD)VRBO
- From $408 per night (USD)
VRBO
House of Classic Arts and Crafts North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming Southold village house sits on a half acre with a back deck overlooking a sweeping backyard. Newly furnish ...
From $408 per night (USD)VRBO
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VRBO
Modern North Fork Retreat with massive pool and Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Newly built farmhouse-style retreat with in-ground pool and private beach access in the heart of the North Fork. This lo ...
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Expedia
Two minuet walk to the beach. On a quiet private road
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Located in the north forks famous wine district. Can sleep up to five. Eat in glassed/screened front porch faces the sou ...
Click For PricingExpedia
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VRBO
Architect-Renovated, Pristine Ranch, Modern Kitchen, Short Walk to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Completely renovated 60's ranch, 2 bedrooms with queen sleeper sofa in family room to sleep 6, new appliances, washer/dr ...
Click For PricingVRBO
- From $700 per night (USD)
VRBO
Beautiful Home with Pool by Wineries and Beaches - “The Vacation House”
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Farmhouse meets beach house at “The Vacation House”…beautiful North Fork Farm House in relaxing farm/beach area perfect ...
From $700 per night (USD)VRBO
- From $990 per night (USD)
VRBO
Sun-Filled 4-BR Home, North Fork - amid Dunes, Beach & Spectacular Sunsets. 3-BA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
We fell in love with this inlet, this neighborhood, this beach, these dunes, and this home the first time we visited in ...
From $990 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
What a cutie pie! This adorable cottage is in one of Southold's most beautiful neighborhoods. If you like to kayak or pa ...
From $335 per night (USD)VRBO
- From $725 per night (USD)
VRBO
Bayfront Vacation Home in Southold, 5 Bedrooms
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Take in the extensive views from this lovely Goose Creek Front waterfront vacation home, with private deck and beach. To ...
From $725 per night (USD)VRBO
- From $999 per night (USD)
VRBO
North Fork Family Villa- large family home with fenced in pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Grand Beach Home, Room For Family and guests. 5 BR, 3.5 BA, Radiant Heat, Gourmet Kitchen With gas Wolf Stove. 10 Foot ...
From $999 per night (USD)VRBO
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VRBO
Experience the North Fork!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This beautifully renovated farmhouse is centrally located next to multiple award-winning wineries which is why we named ...
Click For PricingVRBO
- From $756 per night (USD)
Expedia
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This property is a newly renovated historical Victorian House built in the late 1800's. Each room is furnished with hand ...
From $756 per night (USD)Expedia
- From $667 per night (USD)
VRBO
90 feet of private waterfront w beach, new renovation, panoramic views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious and Luxurious 3 bedroom; brand new construction with 120 feet of waterfront and spectacular sunset views • 2 l ...
From $667 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Privacy!! Heated salt-water pool, central a\/c, all kinds of families welcome
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NO BETTER PLACE TO ENJOY THE BEST OF THE NORTH FORK Due to the utmost care for your family and mine during the worst of ...
From $850 per night (USD)VRBO
- From $735 per night (USD)
VRBO
Shelter Island Waterfront Home!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
A water front home with magnificent Shelter Island Sound views from the entire main area, including living room, porch, ...
From $735 per night (USD)VRBO
- From $1225 per night (USD)
VRBO
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated b ...
From $1225 per night (USD)VRBO
- From $229 per night (USD)
VRBO
Sweet Southold Beach Cottage<br> FALL WINTER SUMMER
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Sweet Southold Beach Cottage Spring/Summer/Fall/Winter Prime location! View Peconic Bay from your driveway! One minute ...
From $229 per night (USD)VRBO
- From $729 per night (USD)
VRBO
North Fork Sound Front Beach House
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Designed by renowned architects Abercrombie & Vieyra for their private use, this 4 bedroom, sound front home with a priv ...
From $729 per night (USD)VRBO
- From $286 per night (USD)
VRBO
RENOVATED SOUTHOLD BEACH COTTAGE - Walk to beach, restaurants, Jitney
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
BEAUTIFUL North Fork Just renovated cottage in Founders Landing Beach Community in Historic Southold Village. ideal for ...
From $286 per night (USD)VRBO
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VRBO
Beautiful brand-new house steps from water!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous brand new, large house overlooking Hashamomack Pond. Steps to boat ramp, and minutes to vineyards, nature prese ...
Click For PricingVRBO
- From $217 per night (USD)
VRBO
Cottage on private road and 5-min walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect all-season cottage with easy access to beaches, wineries, restaurants, and all the great things the North Fork h ...
From $217 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Wineries, Apple Picking, Pumpkin Picking, Outdoor Restaurants and Beaches!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious home great layout for work or school from home. Featured 3-4 bedrooms, 3.5 baths, CAC, hardwood floors, gourmet ...
From $600 per night (USD)Expedia
- From $252 per night (USD)
VRBO
Walk to beach! Simple Cottage Bliss. Peaceful & Private.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 bedroom, 1 bath Ideal for 1-2 couples or a small family. Both bedrooms have queen sized beds, window a/c units, ceili ...
From $252 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, th ...
From $604 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Classic North Fork Beach Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing comfort and privacy on this acre plus setting. Home is crisp, clean and ready for you to enjoy. South Harbors ex ...
From $300 per night (USD)VRBO
- From $567 per night (USD)
VRBO
Lovely home w\/ water views, steps to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
On a quiet peninsula in Southold, this house has everything you need for a North Fork summer or cozy off season. It's fu ...
From $567 per night (USD)VRBO
- From $860 per night (USD)
VRBO
Beautifully appointed waterfront property with heated pool and cabana
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Guests are sure to enjoy a memorable vacation in this fully furnished,4 bedroom 3 bath property. ( The 3rd bathroom is ...
From $860 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
Charming English Tudor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This spacious and charming 4,500 square foot English Tudor is situated on 2.25 acres in Southold. It has 4 bedrooms, 3 b ...
From $1500 per night (USD)Expedia
- From $466 per night (USD)
VRBO
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Steps from Peconic Bay and Cedar beach. Stay in our Southold home in the heart of North Fork and enjoy the best the No ...
From $466 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Beautifully decorated water view resort condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cliffside Resort is located on a bluff overlooking the Long Island sound with beautiful water vistas. The resort has an ...
From $425 per night (USD)VRBO
- From $548 per night (USD)
VRBO
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
World class views of water and sunsets are the signature features of this charming, 3 bedroom house with 90 feet of wate ...
From $548 per night (USD)VRBO
- From $495 per night (USD)
VRBO
Private Coastal Two Bedroom Cottage on the Water
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a ...
From $495 per night (USD)VRBO
- From $669 per night (USD)
VRBO
Water View Beach House just steps to Private Sandy Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Just steps from a private sandy beach with a beautiful view across the Peconic Bay to Sag Harbor and perfect sunsets. Ho ...
From $669 per night (USD)VRBO
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VRBO
Waterfront Oasis on the North Fork
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our creekside home is one of the best places to spend a summer on the North Fork of Long Island. Located steps from a sa ...
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VRBO
Private beach house and Long Island sound views, North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This two bedroom home sits on a lush bluff overlooking the Long Island sound in the North Fork. The guest house with a l ...
Click For PricingVRBO
- From $2000 per night (USD)
VRBO
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layou ...
From $2000 per night (USD)VRBO
- From $2000 per night (USD)
VRBO
Exquisite Private Retreat
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 18
Custom chic private retreat on 2.5 acres in Southold. Enjoy the best of every season in this artfully designed top to b ...
From $2000 per night (USD)VRBO
- From $670 per night (USD)
Expedia
Sea Breeze Paradise: Beachfront & Panoramic Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze Paradise is a newly renovated home. A paradise for those of you who want to enjoy the sun and fresh air with ...
From $670 per night (USD)Expedia
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VRBO
One Story Living across from Private Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Rental Registration #2021-L-49 This lovely one-story home features 3 bedrooms, 3 full baths, a large living room with v ...
Click For PricingVRBO
- From $1257 per night (USD)
Expedia
LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY...
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
Shelter Island Manor LUXURIOUS 2-HOME ESTATE COMPLETELY SECLUDED ON 8 ACRES; PROFESSIONALLY MANICURED GARDENS & HEATED ...
From $1257 per night (USD)Expedia
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VRBO
Farmhouse Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
NORTH FORK The Farmhouse Retreat has been decorated with healing and feng shui top of mind. This home has been newly r ...
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Expedia
Water views Beach and pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious entertainment, relax by the fireplace or relax in the closed porch , Private Beach on the corner of property. E ...
Click For PricingExpedia
- From $1100 per night (USD)
VRBO
Renovated American Farmhouse in the heart of Southold with heated saltwater pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our newly renovated Farmhouse is centrally located in Southold with easy access by bus, train or car. Enjoy your mornin ...
From $1100 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Charming Northfork home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This house is newly updated, beautifully furnished and comfortable. It is light and spacious with hard wood floors throu ...
From $450 per night (USD)VRBO
- From $429 per night (USD)
VRBO
Luxury by the Sea
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your search 👀 is over! Brand New 🔨 Construction. Charming, luxurious, private, comfortable Beach 🏖 House. Stunning ...
From $429 per night (USD)VRBO
- From $400 per night (USD)
VRBO
3 Br North Fork Getaway In Private Beach Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly decorated beach house near vineyards on the north fork. Just steps from a private beach on tranquil goose creek. ...
From $400 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Great Location!! Walk to Town & Train!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a truly unique and beautifully finished historic farmhouse that is comfortable and charming. You can walk to th ...
From $411 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Lovely, Serene and Stylish Country Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
This perfectly placed home is minutes from all that's great about the North Fork: loads of beaches, excellent wineries, ...
From $425 per night (USD)VRBO
- From $1145 per night (USD)
VRBO
North Fork Hideaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our North Fork home is an escape from the real world. We are parked on 3 private acres. There's a heated pool and plenty ...
From $1145 per night (USD)VRBO
- From $1450 per night (USD)
VRBO
Luxurious Estate with Pool by Kenney's Beach, McCabe's Beach and Horton's Point
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
This 6 bedroom estate is situated in Southold, NY, within 10 minutes walking distance of Kenney's and McCabe's beaches. ...
From $1450 per night (USD)VRBO
- Click For Pricing
VRBO
Goose Creek Getaway: Modern Home with Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Goose Creek Getaway is a beautifully remodeled 3-bedroom, 2 full baths North Fork vacation home just a 1-minute drive in ...
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Expedia
Stunning Home & Private Beach on the North Fork
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to a slice of Heaven on the pastoral North Fork. Jaw dropping views, visible from almost every room in the house ...
Click For PricingExpedia
- From $632 per night (USD)
VRBO
Heated pool on Goose Creek, private dock, massive yard walk to beach, wineries
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Southold Permit # 0361. Pool opens Mid April! One season off of a full renovation - reviews before 2022 are from befo ...
From $632 per night (USD)VRBO
- From $600 per night (USD)
Expedia
The North Fork Loft
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Spectacular Waterfront Loft in the heart of The North Forks' Wine Country. Enjoy the tranquil setting at this waterfront ...
From $600 per night (USD)Expedia
- From $777 per night (USD)
VRBO
Waterfront with dock on Goose Creek, just off Peconic Bay and chef's kitchen.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Idyllic North Fork Rental on Goose Creek with Private Dock and Breathtaking Sunset Views. Features Gourmet Chef's Kitche ...
From $777 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
4 Bed \/ 2.5 Bath Stunning North Fork retreat with Heated Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Our home sits on 3+ acres. The Great Room has a stone fireplace and magnificent vaulted ceilings. Sliding doors lead dir ...
From $1200 per night (USD)VRBO
- From $451 per night (USD)
VRBO
Cottage by Cedar Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Cute as a button cottage with 2 bedrooms and 1.5 bath. Oversized outside patio with large teak dining table and huge con ...
From $451 per night (USD)VRBO
- From $950 per night (USD)
Expedia
4BR NOFO Home in Heart of Wine Country (w\/pool)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Newly updated home for your perfect friends and family North Fork getaway. The prime Southold location is minutes away f ...
From $950 per night (USD)Expedia
- From $500 per night (USD)
VRBO
The Stucco House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very unique style house in the area. Updated with newly Gut renovated bathroom and new appliances. Large enclosed porch ...
From $500 per night (USD)VRBO
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Expedia
Seaside Southold Escape in Private Beach Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
There's nothing like fall on the North Fork! Bonfires on the beach, apple & pumpkin picking, corn mazes, vineyards, and ...
Click For PricingExpedia
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VRBO
Cozy Cottage on North Fork
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Cottage. Great Location and nice yard with BBQ and rear deck. Fully furnished Site says I have to have 96 more le ...
Click For PricingVRBO
- From $434 per night (USD)
VRBO
Salt & Sea House - beaches, wineries, farms nearby
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Close to beaches, wineries, farms, and restaurants--the Salt and Sea House is a relaxing North Fork getaway. Uncork a b ...
From $434 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Waterfront, New Construction North Fork Beach House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction ...
From $850 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/3.5 bath newly renovated expansive mode ...
From $1000 per night (USD)Expedia
- From $698 per night (USD)
VRBO
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New Yo ...
From $698 per night (USD)VRBO
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VRBO
On Peconic Bay in Paradise Point with sandy beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Stunning waterfront home, on 2 private acres, in Paradise Point. Brand new renovation! All new baths, updated kitchen, ...
Click For PricingVRBO
- From $315 per night (USD)
VRBO
Charming, Historic Farmhouse close to restaurants, vineyards and beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New to the Market this season! Charming historic 1909 farmhouse with 3 bedrooms and 1 1/2 baths and modern amenities. ...
From $315 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Kid-Friendly Home near the Ocean with Private Gas Grill, Fast WiFi, and Cable
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Classic Southold Country Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Sim ...
From $166 per night (USD)Expedia
- Click For Pricing
VRBO
Kenneys Beach retreat by the Wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This 3 bedroom 2 bathroom Ranch with open floor plan is just a short distance to one of the nicest and sandiest beaches ...
Click For PricingVRBO
- Click For Pricing
VRBO
On the Bay! Your own beach! Looking out at Shelter Island.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience North Fork charm this Summer with your own private beach. Wrap around porch and upstairs deck. Great Food, L ...
Click For PricingVRBO
- From $678 per night (USD)
VRBO
Private Waterfront Home: Dock, Kayaks, Town of Southold, near Greenport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private Waterfront Home is a beautiful home located on the North Fork of Long Island, it has a Master bedroom with a qu ...
From $678 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Two Bed, Two Bath Home Close to Beaches, Vineyards and Breweries
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Make yourself at home in this two bed, two bath home in the heart of North Fork Wine Country! One bedroom has a queen b ...
From $550 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Lovely Waterview Cottage in the Heart of Long Island Wine country
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Peaceful pondfront cottage with two bedrooms , 1 1/2 baths, pull out couch in Living room can sleep two more , and love ...
From $275 per night (USD)VRBO
- From $525 per night (USD)
VRBO
Monthly rental discount of 20%\n\n3 minute walk from a private beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Newly renovated 4 BR 2 Bath home located on a private street with private beach down the road. 3 Bedrooms on the 2nd fl ...
From $525 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Southold, NY- Heart of North Fork Wine Country
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is a Spacious & Meticulous Cape On Great Hogs Neck Peninsula ~ This Charming 4-Plus Bedroom 3.5 Bath Expanded Cape ...
From $425 per night (USD)VRBO
- From $1080 per night (USD)
VRBO
Water front beach house w\/ private beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach front with a private beach. Ideal for sunbathing, swimming, fishing & kayaking. Enjoy daily gorgeous sunset views ...
From $1080 per night (USD)VRBO
- Click For Pricing
VRBO
Cozy Retreat surrounded by Wine Country and Beach Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This retreat is the ultimate country escape. The house has a spacious living space perfect for entertaining or kids. T ...
Click For PricingVRBO
- From $533 per night (USD)
Expedia
Dog-friendly, comfortable home with private pool, large yard, WiFi, & fire pit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Southold Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $533 per night (USD)Expedia
- From $2000 per night (USD)
VRBO
Panoramic Water Views, hot tub, fire pit & easy access to North Fork wine trail
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
All bedrooms have en-suite bathrooms! On the main floor you will find a living room with electric fireplace, modern kit ...
From $2000 per night (USD)VRBO
- Click For Pricing
Expedia
Beach Front House with Amazing Views on Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Freshly renovated beautiful beach front house on private beach. This quaint 2 bedrooms, 1 1/2 bathroom house has centra ...
Click For PricingExpedia
- From $475 per night (USD)
VRBO
Private Beach community home nestled in the heart of Long Island's North Fork
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the Bay Haven Beach Community with large sandy beach, park area on the water, covered picnic area and a consi ...
From $475 per night (USD)VRBO
- Click For Pricing
Expedia
Charming '30s cottage on water overlooking Shelter Island—5 mins from Greenport.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Breezy Shores is like no other place on the North Fork. Our 1930s cottage is set on 80 acres of private, waterfront prop ...
Click For PricingExpedia
- Click For Pricing
Expedia
Southold Sanctuary - North Fork Getaway
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Book your getaway now to the beautiful North Fork of Long Island. This newly renovated 4 bedroom, 2 bathroom house is ce ...
Click For PricingExpedia
- From $692 per night (USD)
VRBO
3 Bedroom NoFo Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the best the North Fork has to offer while staying at our tranquil and peaceful home! Our 3 bedroom, 2 bathroom ho ...
From $692 per night (USD)VRBO