Vacation Rentals in Southold, New York
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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
- 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
- bedrooms 3
- community Southold Shores
- rental type House
- sleeps 5
- baths 2
- rates (USD)
$600
- $2,200
/wk
- bedrooms 3
- community Southold Shores
- rental type House
owner badge
- sleeps 7
- baths 2
- rates (USD)
$228
- $350
/nt
$1,600 - $2,400 /wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2½
- rates (USD)
$2,800
- $3,200
/wk
$11,200 - $12,800 /mth
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