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Vacation Rentals in Southold, New York

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about Southold

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Southold, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Southold are added and updated every week!

Compared to hotels, Southold vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Southold, New York Vacation Rentals and Tourism

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Southold things to do

 

One Woman Wines & Vineyard

I've been ruminating over my experience here. Quite yet powerful. Intimate but serious. Precise yet easy going. Gabrielle, daughter to the proprietor, over...read more

 

Sparkling Pointe

Not at all intimate. Think overly giddy "brides maids showing up in club wear & arriving in white limos" argh. Or an enterage of "Housewives of some NYC...read more

 

Mattebella Vineyards

We stopped here to celebrate after my fiance proposed to me at Lavender by the Bay in East Marion last weekend. This was our last wine tasting stop of the...read more

 

Sannino's Bella Vita Vineyard

I took my wife wine touring this past weekend. After stopping at Duck Walk we quickly left when we walked in and saw 200 drunk early 20 something's from a...read more

 

Raphael Vineyard and Winery

Raphael Vineyards is a beautiful location to visit. The inside is grand with huge chandeliers and a wonderful circle bar in the middle as the focal point....read more

 

McCall Wines

This is wholly NOT big, corporate, shiny or loud. It's the ultimate opposite. From the unobtrusive barn, laid back setting, to the stables turned into...read more

 

Croteaux Vineyards

This was my first foray into LI vineyard wine tasting and this was a great first stop. They don't allow commercial buses to drop off to the overall vibe is...read more

 

Pindar Vineyards

I'm giving this place 4 stars for two big reasons: 1. They allow dogs 2. They allow you to bring your own food so long as you eat at the covered patio way...read more

 

Lieb Cellars

As a service industry professional (read: waitress with many years of experience), I tend to be pretty forgiving when it comes to service. It takes a lot to...read more

 

The Lenz Winery

This is a classic Long Island winery that offers something truly unique to the area - some world class wines! Our group was greeted enthusiastically, and...read more

 

Coffee Pot Cellars

Spent a day touring the north fork wineries and visited Coffee Pot on the recommendation of another winery we visited. It's a tiny, quaint location right on...read more

 

The Winemaker Studio

One of those "hidden gems" in the North Fork. Each time I get to stop by, I am thoroughly impressed. They offer wines from various winemakers and also...read more

 

Duck Walk Vineyards

This was stop #2 out of 3 for our bus tour of the LI vineyards. The facility is a nice looking space with a beautiful back area to hang out and basque in...read more

 

Kontokosta Winery

The location is spectacular. I believe it's the further most winery on the N Fork. The green vineyard runs along the long road leading into the winery which...read more

 

Bedell Cellars

Imagine row upon row of grapes amid a lush, bucolic setting. This has got to be one of the best "backyards" I've even seen. There's also a lovely back...read more

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Luxury Wine Country Beach House for less than a Hotel Room
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $228 - $350 /nt
    $1,600 - $2,400 /wk
 
 
 
 
 

57 reviews write a review

North Fork Beach House
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $170 - $315 /nt
    $500 - $2,200 /wk
 
 
 
 
 

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North Fork Lake House
Southold House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,800 - $3,200 /wk
    $11,200 - $12,800 /mth
 
 
 
 
 

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Waterfront, pool, golf much more! WEEKNTS $500 Sept/Oct BOOK NOW!
Southold House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $250 - $1,500 /nt
 
 
 
 
 

128 reviews write a review

New Listing! "The Sheridan House" 2BR Long Island Cottage in Southold w/Wifi & Private Beach Access - 100 Yards from the Beach & Near North Fork Wineries!
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD) $180 /nt
    $900 /wk
    $5,400 /mth
 
 
 
 
 

1 reviews write a review

Town Harbor Lane, Founders Landing Beach, Southold, North Fork, LI, NY
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $1,599 - $1,799 /wk
    $6,000 /mth
 
 
 
 
 

1 reviews write a review

Charming 2BR in Heart of North Fork. Walk to Sandy Bay Beach
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $325 - $350 /nt
    $2,100 - $2,400 /wk
 
 
 
 
 

14 reviews write a review

Secluded Cottage on Lake - Walk to Sound Beach
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $200 - $250 /nt
    $1,500 /wk
 
 
 
 
 

39 reviews write a review

Waterview 3 BR Luxury Beach House for Less Than a Hotel Room
Southold House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $250 - $343 /nt
    $1,600 - $2,400 /wk
 
 
 
 
 

57 reviews write a review

Southold Soundfront Private Beach
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $400 - $475 /nt
    $3,300 /wk
    $12,750 /mth
 
 
 
 
 

6 reviews write a review

Fully Furnished Home, Heart Of Long Island Wine Country, Walk To Many Spots!
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 13
  • baths 3
  • rates (USD) $386 - $500 /nt
    $2,700 /wk
 
 
 
 
 

2 reviews write a review

Beach Front in Southold; newly renovated/baths/kitchen/2nd floor family room!
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $499 - $750 /nt
    $3,497 - $4,375 /wk
    $9,348 /mth
 
 
 
 
 

3 reviews write a review

Beach house in wine country; huge sun room, all new renovation,designer interior
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $295 - $475 /nt
    $1,800 - $2,800 /wk
 
 
 
 
 

6 reviews write a review

Location Location, Charming Cottage, a block from beach, Town, close to Vineyars
Southold Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $257 - $600 /nt
    $6,500 - $12,000 /mth
 
 
 
 
 

9 reviews write a review

Lighthouse Inspired Lakefront Beach House, Overlooking LI Sound
Southold House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $257 - $350 /nt
    $1,800 /wk
    $6,000 /mth
 
 
 
 
 

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Waterfront Home/ Private Beachcommunity/ Heart of Wine Country
Southold House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $642 - $3,500 /wk
    $2,750 - $13,000 /mth
 
 
 
 
 

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Sunny 4 Bed / 2 Bath Summer Home Steps from Private Beach
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,700 - $3,500 /wk
 
 
 
 
 

13 reviews write a review

Walk barefoot to the beach...
Southold Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $457 - $800 /nt
    $1,800 /wk
    $5,000 - $12,000 /mth
 
 
 
 
 

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