Southold Rentals
- From $200 per night (USD)
VRBO
Charming home with fireplace, kayaks, patio, fast WiFi, & washer\/dryer-dogs ok
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Minnehaha Marvel Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $200 per night (USD)VRBO
- From $608 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 $608 per night (USD)VRBO
- Click For Pricing
VRBO
Cute and simple summer cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked in a shady private road in the heart of the North Fork wine district with access to the white sandy beach of the ...
Click For PricingVRBO
- From $925 per night (USD)
Expedia
Greenport Village walking distance to all
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
3 bedroom 2 floor cape with large great room and enclosed patio perfect for families and small groups. Relax in the hot ...
From $925 per night (USD)Expedia
- From $539 per night (USD)
VRBO
Peconic Sound Beach Home: Backyard & Vineyards
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Peconic Sound Beach Home in Peconoc Southold is a quaint beach cottage that has a charming allure. Enjoy your access to ...
From $539 per night (USD)VRBO
- From $556 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 $556 per night (USD)Expedia
- From $270 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 $270 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 $404 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 $404 per night (USD)VRBO
- From $363 per night (USD)
VRBO
North Beach Fork Beach House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy our tranquil home in a private beach community.Located on a half acre of private land, this home has all the ameni ...
From $363 per night (USD)VRBO
- From $395 per night (USD)
VRBO
A Natural Getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This is a sunny family-welcoming pet-friendly house (Rental permit 0343) built in 2019 on a woodsy acre-plus. The home i ...
From $395 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Three Bed, Three Bath Home Close to Beaches, Vineyards and Breweries
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Make yourself at home in this recently renovated home in the heart of the North Fork Wine Country! With three bedrooms ...
From $800 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 $1000 per night (USD)
VRBO
Beautiful condo on the Long Island Sound in a resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is one of the nicest decorated in Cliffside. Gorgeous shiplap walls with navy accents. It has a beautiful f ...
From $1000 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 $700 per night (USD)
VRBO
Greenport Waterfront Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
GREENPORT CONKLING PT CREEKFRONT MINT 3BR COTTAGE W/PRIME VIEWS - This cottage on a half-acre lot fronts on the pristine ...
From $700 per night (USD)VRBO
- From $395 per night (USD)
VRBO
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)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 $512 per night (USD)
VRBO
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront Water's Edge luxury suite, Suite C-204 accommodates up to 6 guests (see below) with two bedrooms and two bath ...
From $512 per night (USD)VRBO
- From $380 per night (USD)
VRBO
The Cottage at Sunset Bluff
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This newly renovated charming cottage is sure to spark your romantic side. Located just steps away from the Long Island ...
From $380 per night (USD)VRBO
- From $920 per night (USD)
VRBO
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Completely renovated 3 bedroom, 2 bath Beachfront Cottage. Step outside and enjoy outdoor dining, playing games on th ...
From $920 per night (USD)VRBO
- From $625 per night (USD)
VRBO
Beautiful Soundfront condominium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bathroom direct sound front condo in greenport at Cliffside resort direct view. heated pool, beac ...
From $625 per night (USD)VRBO
- From $899 per night (USD)
VRBO
PRIVATE RETREAT-POOL-WALK TO BEACH- 2.5 MILES TO VILLAGE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous 4 bedroom, 3.5 bath house with a fenced in pool, primely located close to everything Greenport has to offer & i ...
From $899 per night (USD)VRBO
- From $899 per night (USD)
Expedia
PRIVATE SEA BREEZE WITH A VIEW
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and unwind, while watching the water views from the deck. This bright and airy home is inviting, yet private and h ...
From $899 per night (USD)Expedia
- From $604 per night (USD)
VRBO
Bright Oasis in Beautiful North Fork Wine Country
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this idyllic family friendly home in the heart of North Fork, Long Island. It's a newly renovated and spacious 4 b ...
From $604 per night (USD)VRBO
- From $1630 per night (USD)
Expedia
Contemporary Colonial home with pristine Peconic bay views, steps to...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Vineyard Beach House Contemporary Colonial home with pristine Peconic bay views, steps to private beach and dock, Weber ...
From $1630 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Peaceful 2 BR Perfect for Family Weekend Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This home is ideal for your family. It includes two bedrooms, one with a queen bed and the other with three twin beds. I ...
From $399 per night (USD)VRBO
- From $715 per night (USD)
Expedia
Cozy Long Island Escape
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy all the beauty of Long Island’s North Fork with this conveniently located farmhouse. Close to wineries, farms and ...
From $715 per night (USD)Expedia
- From $935 per night (USD)
VRBO
5BR NOFO Beach House, heated, saltwater pool, walk to private beach!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to our modern beach house, boasting all the amenities you could ask for including 5 BR (the 6th BR is in the off ...
From $935 per night (USD)VRBO
- From $402 per night (USD)
VRBO
Charming Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming cozy cottage located in the heart of the Northfork, East End of Long Island. Come explore the beautiful vineyar ...
From $402 per night (USD)VRBO
- From $760 per night (USD)
VRBO
Beach House near Greenport Village
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom with deeded beach rights and partial water view. 5 minute walk to the beach and short drive to the heart of th ...
From $760 per night (USD)VRBO
- From $1063 per night (USD)
VRBO
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 12
Town of Southold Rental Permit Number 0816 A beautiful brand new estate home with a heated pool, situated in t ...
From $1063 per night (USD)VRBO
- From $1126 per night (USD)
VRBO
Greenport 'Sunshine Home'
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This welcoming colonial is situated on three-fourths of an acre. Family friendly, the house is perfect for your time awa ...
From $1126 per night (USD)VRBO
- Click For Pricing
VRBO
North Fork Getaway with Water Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious home has beautiful water views and is a perfect base for exploring all that the North Fork has to offer. W ...
Click For PricingVRBO
- From $750 per night (USD)
VRBO
Coastal Getaway, water views, walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Bea ...
From $750 per night (USD)VRBO
- From $839 per night (USD)
Expedia
Historic North Fork retreat, large pool, deck, overlooks preserved land,...
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 10
North Fork Gem Historic North Fork retreat, large pool, deck, overlooks preserved land, lovely sunsets, and minutes to ...
From $839 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
- Click For Pricing
Expedia
Beautiful private home with beach access down the block
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
1/2 acre fenced property. open floor plan. Master with en suite bathroom. additional bedrooms and bathrooms for your use ...
Click For PricingExpedia
- From $909 per night (USD)
VRBO
Amazing Beach House in the North Fork Wineries
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Heart of wine country, steps from the beach, minutes to Greenport. Spacious 3 bedroom/ 2.5 bath boasts vaulted ceilings ...
From $909 per night (USD)VRBO
- Click For Pricing
Expedia
Southold by the bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful ranch style home within walking distance of the beach. Has a large backyard and deck for entertaining. Featur ...
Click For PricingExpedia
- Click For Pricing
VRBO
North Fork Waterfront 4-bedroom Home w\/Pool & Dock
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
The whole family will enjoy this waterfront home with lots of room for fun. Pool, dock and large great room offers ample ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $543 per night (USD)
VRBO
4BR+ Newly renovated home mins to top beaches and vineyards, new heated pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This is a newly renovated 4BR+ home in the heart of Southold with a brand new 18 x 36 heated pool and fully fenced yard. ...
From $543 per night (USD)VRBO
- 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 $1143 per night (USD)
VRBO
Sandy Bay Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Stunning waterfront location with amazing sugar sand beach! Well proportioned home with beautiful symmetry. The centra ...
From $1143 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
- Click For Pricing
VRBO
Entire Loft-Walk to Town, Beach, Train, Wine Trail
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Relax in this newly renovated, light-filled, well appointed garden loft. Centrally located off Main street on a quiet pr ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $450 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 $450 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
- From $388 per night (USD)
VRBO
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 $388 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)
VRBO
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)VRBO
- From $247 per night (USD)
Expedia
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)Expedia
- From $615 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 $615 per night (USD)VRBO
- Click For Pricing
Expedia
Long Island Vacation Rental w\/ Pool Near Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Plan your next getaway to Suffolk County, New York, to experience Long Island’s laid-back lifestyle, white sands, and aw ...
Click For PricingExpedia
- From $520 per night (USD)
VRBO
NorthFork \nPeaceful Peconic Getaway- center of Wine Country
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly refurbished ranch style home in the heart of the North Fork wine country and close to all the best beaches , farms ...
From $520 per night (USD)VRBO
- Click For Pricing
Expedia
LI Sound view, walk to beaches,lake access\/kayaking, fishing
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Water views from every room of LI Sound and Great Pond. Walk to beautiful sound beaches and watch the sunset from the de ...
Click For PricingExpedia
- Click For Pricing
VRBO
Private Guest Room-heart of Long Island's North Fork wine country-steps to beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small clean guestroom with private entrance and private bath located on private road with minimal traffic. Free onsite p ...
Click For PricingVRBO
- From $831 per night (USD)
VRBO
North Fork Waterfront Spectacular Views Cottage circa 1930
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
North Fork Waterfront Spectacular Views Cottage circa 1930' On Golden Pond' Private road, amazing waterfront vie ...
From $831 per night (USD)VRBO
- From $800 per night (USD)
VRBO
Waterfront Beach House Gem with Bay Views Steps to Pipes Cove!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Our Greenport beach house is steps from Pipes Cove Beach with beach access, water views from the house, a big yard, and ...
From $800 per night (USD)VRBO
- From $880 per night (USD)
VRBO
Newly Renovated Gem on the Cedar Beach Peninsula!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Come and experience the peaceful tranquility of the North Fork with this newly renovated gem in the heart of Southold. I ...
From $880 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Beautiful North Fork 3-Bedroom Home Steps Away from a Private Sandy Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful vacation home in the Bay Haven community of Southold. The house is on a fully landscaped property of over a th ...
From $399 per night (USD)VRBO
- From $724 per night (USD)
Expedia
Waterfront property with own dock and stunning views, overlooking Southold Bay.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our home, a one of a kind Bayfront property with a private dock, a large, expansive deck, overlooking Southol ...
From $724 per night (USD)Expedia
- Click For Pricing
VRBO
NEW - Tranquil Farm Setting In The Heart Of North Fork
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Tranquil farm setting in the heart of North Fork, close to all. Centrally located to all the North Fork has to offer, b ...
Click For PricingVRBO
- From $1532 per night (USD)
Expedia
Gorgeous Greenport Beach House right on the Sound! Breathtaking views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to Villa Sonore. A gorgeous beachfront home in Greenport located right on the LI Sound. Walk to restaurants and ...
From $1532 per night (USD)Expedia
- From $122 per night (USD)
VRBO
Southold Cottage w\/ Patio & Grill - Walk to Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
If you’re a nature lover, a beach lover, a wine lover, or just in need of an escape, plan your dates for a stay at this ...
From $122 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
- From $788 per night (USD)
VRBO
Serene bay front home with a private beach, deck, board games, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watersedge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $788 per night (USD)VRBO
- From $600 per night (USD)
Expedia
Warm Peconic home…short walk to a private beach.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Minimum 14 day rental required (as per Town of Southold) Quaint cozy quiet private road short walk to sandy private bea ...
From $600 per night (USD)Expedia
- From $208 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 $208 per night (USD)VRBO
- From $545 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 $545 per night (USD)Expedia
- From $594 per night (USD)
VRBO
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King 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 B ...
From $594 per night (USD)VRBO
- From $550 per night (USD)
Expedia
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 $550 per night (USD)Expedia
- From $600 per night (USD)
VRBO
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 $600 per night (USD)VRBO
- From $850 per night (USD)
VRBO
North Fork Waterfront Gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Live the waterfront life! Kayak, paddle board, boat from your front door! Enjoy gathering your own oysters and clams fro ...
From $850 per night (USD)VRBO
- From $321 per night (USD)
VRBO
SPRING DISCOUNT - COTTAGE ON LONG ISLAND SOUND, PRIVATE BEACH, GLORIOUS SUNSETS
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This charming cedar shingled beach cottage is located steps away from Long Island Sound with stairs leading down to its ...
From $321 per night (USD)VRBO
- From $630 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 $630 per night (USD)VRBO
- From $961 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 $961 per night (USD)VRBO
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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 $550 per night (USD)
VRBO
Secluded charmer with new heated gunnite pool and steps to beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Built in 1928, this gorgeous shingled home is fully equipped to host your getaway. You're within easy walking distance o ...
From $550 per night (USD)VRBO
- From $308 per night (USD)
Expedia
Well-appointed coastal home with large yard, pool, basketball, & outdoor kitchen
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Secret Garden Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $308 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Horton House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Horton House, located in the historic district of Southold, NY, is one of the oldest English houses in the state. Loving ...
From $385 per night (USD)VRBO
- From $949 per night (USD)
Expedia
Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail,...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wine Trail Waterfront Waterfront Beach House Nestled Along the Wondrous North Fork Wine Trail, Perfect for Families 4B ...
From $949 per night (USD)Expedia
- From $1210 per night (USD)
VRBO
STATELY, PEACEFUL & TASTEFUL WITH SPARKLING POOL AND FIREPLACES
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful home on gorgeous tree-lined street in Southold on the North Fork, Long Island. Near Greenport, Orient, Shelter ...
From $1210 per night (USD)VRBO
- From $1179 per night (USD)
VRBO
A cozy and family-friendly haven with heated pool, minutes from the beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
A family-friendly home that covers all the bases. Everything your family needs (toys, cribs, bouncers, tub, playmats, hi ...
From $1179 per night (USD)VRBO
- From $1143 per night (USD)
VRBO
Waterfront Historic Artist’s Home, with private beach, July 26 to August 9
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Beachfront Historic Artist’s Residence If you’re looking for two amazing weeks in late July/ early August, July 26 to ...
From $1143 per night (USD)VRBO
- From $1413 per night (USD)
VRBO
Sandpoint by Rove Travel | Modern 5BR w\/ Pool
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to Sandpoint, a Rove Travel Home! Rove is a brand of luxury property rentals designed for the modern ...
From $1413 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful and quiet corner home in a lovely neighborhood in Southold. 100 year old farmhouse but with modern convenienc ...
From $360 per night (USD)VRBO
- From $685 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 $685 per night (USD)Expedia
- Click For Pricing
Expedia
Farmhouse Oasis with Vineyard Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Unwind and soak in summer at this incredibly charming North Fork farmhouse. Private back yard with in-ground heated poo ...
Click For PricingExpedia
- Click For Pricing
Expedia
Palm Springs Vibes on the North Fork
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel the happy vibes of Palm Springs with a fully guy renovated ranch home on an acre of land. Brand new appliances. Clo ...
Click For PricingExpedia
- From $780 per night (USD)
VRBO
Modern North Fork Haven: Beachfront,Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
As you step into this charming stunning and newly constructed home beachfront oasis, you'll be greeted by a spacious and ...
From $780 per night (USD)VRBO
- From $750 per night (USD)
VRBO
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 $750 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Enjoy the North Fork of Long Island at Our Lovely Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Hi everyone: I think the photos do a better job of showing the property than I could do by describing it. But we do have ...
From $350 per night (USD)VRBO
- From $1414 per night (USD)
Expedia
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 $1414 per night (USD)Expedia
- From $920 per night (USD)
VRBO
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 $920 per night (USD)VRBO
- From $1300 per night (USD)
Expedia
North Fork Waterfront Home - Lots of Room - Luxurious Comfort
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Waterfront private dock-Luxury comfort on North Fork -perfect for family fun-Lots of room Amenities include newly renova ...
From $1300 per night (USD)Expedia