Southold Rentals
- From $502 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 $502 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- Click For Pricing
VRBO
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 PricingVRBO
- 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 $1500 per night (USD)
VRBO
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)VRBO
- From $2000 per night (USD)
Expedia
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)Expedia
- From $663 per night (USD)
VRBO
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 $663 per night (USD)VRBO
- From $436 per night (USD)
Expedia
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 $436 per night (USD)Expedia
- From $300 per night (USD)
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 ...
From $300 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
- Click For Pricing
VRBO
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 PricingVRBO
- From $141 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 $141 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Waterfront Retreat Easy Walk to Pristine Beaches & Near Wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Waterfront retreat in quiet, tree lined neighborhood. Enjoy Summer days out on the spacious wrap-around deck, go upsstai ...
From $300 per night (USD)VRBO
- From $673 per night (USD)
Expedia
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 $673 per night (USD)Expedia
- 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 $475 per night (USD)
Expedia
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)Expedia
- From $600 per night (USD)
VRBO
Southold Soundfront Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom PERFECT beach house located on a private beach. If you love the beach, fishing, swimming and sunsets in a qu ...
From $600 per night (USD)VRBO
- From $398 per night (USD)
Expedia
Steve's Place: Heated Pool, 3BR Southold Home, Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Steve's Place is a beautifully and professionally decorated 3-bedroom with 1.5 bathrooms, North fork vacation home is ju ...
From $398 per night (USD)Expedia
- From $195 per night (USD)
VRBO
A Natural Getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This lovely stroll-to-the beach "farmhouse," built in 2019 on a woodsy acre, is bright, beach-walkable and centrally-loc ...
From $195 per night (USD)VRBO
- From $395 per night (USD)
Expedia
Fabulous Waterfront Property in the Heart of Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The beauty of this newly remodeled house in the heart of wine country is unparalleled on the North Fork. Pull up to the ...
From $395 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Greenport Walk to beach & vineyard from this brand new home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this brand new unique retreat. Walking to distance to the beach and winery. Less than a 2 minute drive ...
From $600 per night (USD)VRBO
- From $1226 per night (USD)
VRBO
5 bed, 4.5 bath home on 1.24 acres w\/ pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Perfect summer getaway with 5 bed, 4.5 bath in the heart of the North Fork. The home sits on 1.24 acres and features an ...
From $1226 per night (USD)VRBO
- From $243 per night (USD)
VRBO
Paradise Shores Beach Cottage | Cottage in Southold near private beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Paradise Shores Beach Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $243 per night (USD)VRBO
- From $559 per night (USD)
Expedia
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE ...
From $559 per night (USD)Expedia
- From $998 per night (USD)
VRBO
Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront Chic Cozy North Fork Home with Direct Water Access, Private Dock, Close to Wineries 4BR/3BA: private pool, ...
From $998 per night (USD)VRBO
- Click For Pricing
Expedia
Enjoy all seasons in this beautiful North Fork Cottage perfectly located!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our North Fork cottage. Situated in a quiet cul-de-sac in Southold, our home is minutes from the tranquil bea ...
Click For PricingExpedia
- From $559 per night (USD)
VRBO
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE ...
From $559 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CHECK OUT OUR REDUCED SEASONAL RATES 6 WINERIES IN UNDER A MILE NO CLEANING FEES NO EXTRA PERSON FEES FREE BIKES FREE B ...
From $604 per night (USD)Expedia
- From $1437 per night (USD)
VRBO
Beautiful waterfront home with pool, hot tub dock kayaks bocce etc Sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Amidst north fork wineries steps from sandy beach. Private dock, kayaks, paddle board, private community. Spacious 5 b ...
From $1437 per night (USD)VRBO
- From $962 per night (USD)
Expedia
Perfect Retreat for Families - Close to Amazing Wineries, Beaches, and Dining!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy the NOFO life - full of farm to table food, amazing oysters, and beaches! This newly renovated stylish house sle ...
From $962 per night (USD)Expedia
- From $714 per night (USD)
VRBO
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
You are invited to have a wonderful time in this Southold, Long Island beach house. You will have a fabulous time of sun ...
From $714 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Beautiful Southold Home with a Water View - 3 Bedroom, 2.5 Bath, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
My home is a hidden gem tucked away in a beautiful and quiet neighborhood in Southold, NY. With beautiful water views an ...
From $300 per night (USD)VRBO
- From $451 per night (USD)
VRBO
KENNEY’s BEACH: SOUTHOLD BEACH COTTAGE Waterview, walk to Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
KENNEY’s BEACH, Southold Beach Cottage. This bright, airy, sparkling clean waterview Beach Cottage, sleeps 3-4. The Home ...
From $451 per night (USD)VRBO
- From $742 per night (USD)
VRBO
Beach Front in Southold; newly renovated\/baths\/kitchen\/2nd floor family room!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Newly renovated with two full bathrooms, kitchen and second floor entertainment/family/ bedroom with glorious views over ...
From $742 per night (USD)VRBO
- From $385 per night (USD)
VRBO
Southold home at Kenney's Beach 4 bedrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Lovely, spacious home with open, airy floor plan, featuring four bedrooms at Kenney's beach in Southold. First floor has ...
From $385 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Located in the heart of wine country\/BEACHES\/shops.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Historical home full of charm. A home built in the 1700's this home maintains the historical feel with all the amenitie ...
From $450 per night (USD)VRBO
- From $360 per night (USD)
VRBO
North fork Private exclusive Residence for Rent
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 8
Spacious 3 bedroom ...3 1/2 bathroom modern house with large swimming pool .close to the beach and vine yards. Large ea ...
From $360 per night (USD)VRBO
- From $3000 per night (USD)
VRBO
HEATED POOL waterfront HOT TUB, GYM, Watersports, BOATER DELIGHT luxury modern
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Brand new heated gunite saltwater pool!!!! A sparkling clean and modern 6 bedroom, 4 bath waterfront home offering all t ...
From $3000 per night (USD)VRBO
- From $407 per night (USD)
VRBO
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great location close to all the North Fork has to offer. The entire upstairs of an Historic Home built in the 1830's wi ...
From $407 per night (USD)VRBO
- 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
- From $753 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 $753 per night (USD)VRBO
- 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
- 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
- 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
- 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
- From $350 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 $350 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 $723 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 $723 per night (USD)VRBO
- Click For Pricing
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 $950 per night (USD)
VRBO
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)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 $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 $957 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 $957 per night (USD)VRBO
- From $1250 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 $1250 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Boutique Waterfront Home w\/ Pool in Southold, LI
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This beautiful home is located on scenic Corey Creek in Southold. There is truly no better place to get away from it all ...
From $286 per night (USD)VRBO
- Click For Pricing
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 ...
Click For PricingVRBO
- From $1411 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 $1411 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 $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 $615 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 $615 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
- Click For Pricing
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 ...
Click For PricingVRBO
- From $655 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 $655 per night (USD)VRBO
- From $879 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 $879 per night (USD)VRBO
- From $365 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 $365 per night (USD)VRBO
- From $234 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 $234 per night (USD)VRBO
- From $641 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 $641 per night (USD)Expedia
- Click For Pricing
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 $1375 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 $1375 per night (USD)VRBO
- 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 $643 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 $643 per night (USD)VRBO
- From $883 per night (USD)
VRBO
Heated Saltwater Pool, Near Beach & Wineries
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Wonderfully newly appointed spacious retreat near Kenney's Beach, wineries and Southold town, featuring 4 bedrooms and 3 ...
From $883 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 $227 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 $227 per night (USD)VRBO
- From $276 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 $276 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 $877 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 $877 per night (USD)VRBO
- From $406 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 $406 per night (USD)VRBO
- From $392 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 $392 per night (USD)VRBO
- From $920 per night (USD)
Expedia
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 $920 per night (USD)Expedia
- 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 $422 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 $422 per night (USD)VRBO
- From $850 per night (USD)
VRBO
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)VRBO
- 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
- Click For Pricing
VRBO
Southold near vineyard & beach
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 0
Enjoy a stylish experience at this centrally-located historic charmer. Have cocktails on the balcony, cook in the fully ...
Click For PricingVRBO
- From $862 per night (USD)
Expedia
Eat, Love, Stay, Wellness Southold North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Walking distance from Jitney, LIRR & Southold village. Deck, indoor soaking tub & outdoor shower. Book separately massag ...
From $862 per night (USD)Expedia
- From $625 per night (USD)
VRBO
Quite Neighborhood with Private Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Great location with water views in a quiet neighborhood with private beach access! Perfect rental for families to enjoy ...
From $625 per night (USD)VRBO
- From $822 per night (USD)
Expedia
Newly Constructed Modern Vacation Villa Minutes to some of the best...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Villa Vino Modern Newly Constructed Modern Vacation Villa Minutes to some of the best wineries on the North Fork, Perfe ...
From $822 per night (USD)Expedia
- Click For Pricing
Expedia
Sandy Bay Getaway: Close to Beach & Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 2-level home has 4 beds and 3 baths that can comfortably sleep 8. Outside, guests will find the fenced yard, patio, ...
Click For PricingExpedia
- From $425 per night (USD)
Expedia
Sprawling waterfront home with bikes, kayaks, pool table, and grill - dogs ok
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
The North Fork Beach House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $425 per night (USD)Expedia
- From $247 per night (USD)
VRBO
Beautiful garden-view home near the water with lawn, streaming, W\/D, AC, kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Elegant Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $247 per night (USD)VRBO
- From $556 per night (USD)
VRBO
Sweeping Dunes Beach Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Take it easy at this unique and tranquil getaway. This newly renovated beach cottage is located on a private property on ...
From $556 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Serenity on the North Fork
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Mediterranean style newly renovated home on a private waterfront property. Enjoy beautiful sunsets and views of the Lon ...
From $800 per night (USD)VRBO
- From $425 per night (USD)
Expedia
North Fork Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Keep it simple at this peaceful and centrally-located light filled north fork cottage. Creek views with large yard and m ...
From $425 per night (USD)Expedia
- Click For Pricing
VRBO
Historic cottage near the NoFo beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We are renting our warm, wonderful and rustic 3 bedroom cottage in Southold for parts of July and August. We are steps f ...
Click For PricingVRBO
- From $442 per night (USD)
VRBO
Kenney's Beach House, Short Walk to Best Swimming and Sunset Sound Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Beautifully appointed and ultra-comfortable home with sunny, sky-lit, open floor plan. 2+ Bed/2 Bath Southold getaway w ...
From $442 per night (USD)VRBO
- From $280 per night (USD)
VRBO
House central to North Fork wineries restaurants + beaches. Walk to town.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Comfortable House on a quiet private road 0.5 mile to Southold town center. Would work well for a small family or two co ...
From $280 per night (USD)VRBO
- Click For Pricing
VRBO
Northfork Waterfront Bungalow. Deep water dock. Paradise
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Quintessential, rustic, Hamptons bungalow dream. As waterfront as you can get without being on a boat. A deep water dock ...
Click For PricingVRBO