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Vacation Rentals in Southold, New York

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

 

Sparkling Pointe

Sparkling Pointe...the name alone draws you in, the French flag flying out front seals the deal. Of all the vineyards on Long Island, Sparkling Pointe...read more

 

One Woman Wines & Vineyard

Love going to this winery, here is the reason why: It is a family run vineyard with a nice selection of wines, mainly whites, one delicious Merlot, from...read more

 

Croteaux Vineyards

My first time here.. I was impressed! It's a romantic winery.. The ambiance is very much relaxing.. On weekdays very quiet.. Just let the time pass while...read more

 

Mattebella Vineyards

Vineyard We were tooling about the east end and looking for open vineyards - not an easy feat in the winter, and we drove past Mattebella, which had an...read more

 

Duck Walk Vineyards

If you want a rowdy college party - go to their north fork location. Horrible, loud, bar is jammed and the place looks like they are selling kmart wine. ....read more

 

Corey Creek Winery

This winery is related with Bedell winery. They carry some labels from Bedell and gift products as well. Winery itself is beautiful and spacey. Tasting was...read more

 

Old Field Vineyards

Quack I love a place that has wildlife roaming around and as soon as we pulled into the old Field Vineyards, we were greeted by some ducks waddling around...read more

 

Mc Cabes Beach

This beach is part of the Southold Town Beaches. The residents and guests in the hamlets of Southold Town can obtain a beach sticker and have exclusive use...read more

 

McCall Wines

McCall is by far the best vineyard on the North Fork. I think J.W.'s review was on point. It's a small vineyard, with an amazing staff, and though it's...read more

 

The Lenz Winery

OMG, would you folks grow a pair? Think about what happens at a vineyard, They are trying to run a business on the east end of Long Island. Its not all Rose...read more

 

Raphael Vineyard and Winery

This winery is my favorite on the North Fork of the island. Not only is the wine delicious, but the winery itself really has that 'wow' factor. I first...read more

 

The Winemaker Studio

The Winemaker Studio occupies the space of what was once The Tasting Room. I never had a chance to visit that place before it closed, but I hear it was a...read more

 

Wolffer Estate Vineyard

This was my first wine tasting at a vineyard and it was the perfect outing for a not so great beach day. I was told that they are "different from other...read more

 

Pindar Vineyards

If this isn't my first stop when I hit the East End, then TRUST I will find my way there by the end of the day. Back in 2008, when my husband and I first...read more

 

Shinn Estate Vineyards

Yum! I absolutely loved the wines here. My favorites were the steel fermented Chardonnay and the Rose. The grappa was way too strong for me personally, but...read more

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Lighthouse Inspired Lakefront Beach House, Steps to LI Sound
Southold House Rental Picture
  • bedrooms 4
  • community Kenney's Beach Civic
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,800 - $2,800 /wk
    $6,850 - $10,000 /mth
 
 
 
 
 

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North Fork Beach House
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • sleeps 5
  • baths 2
  • rates (USD) $600 - $2,200 /wk
 
 
 
 
 

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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
 
 
 
 
 

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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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