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
My friends and I stumbled upon this place while we were doing a little wine hopping on memorial day weekend. We had no idea where our next location was...read more
One Woman Wines & Vineyard
In the course of a year and a half, One Woman Vineyards and Winery has become one of my favorite wineries on the North Fork of Long Island. They made a...read more
Croteaux Vineyards
"At Last" After almost 25 years I have discovered a Wine From Long Island That I love. ! We went out East last Sunday to visit some new wineries that we...read more
Mattebella Vineyards
Went here at the tail end of a Monday in mid April, not exactly a hoppin' time out on the north fork. My girlfriend and I rented bikes and checked out some...read more
Duck Walk Vineyards
My friend's and I were here this weekend. My 3rd trip to this vineyard and their first. We got here around 1pm. Crowds started building but we still got a...read more
Corey Creek Winery
One of my favorite wineries on the North Fork! Great spot to stop after a few tastings and share a picnic and a bottle of wine on the back deck overlooking...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
Raphael Vineyard and Winery
My friends and I were here past weekend and we were warned by a lady that we bumped into at a different vineyard about how rude Raphael's staff was. We went...read more
The Lenz Winery
I was recommended to come here by a few friends who are a bit of a wine buff, so why not. My friends and I came here and it just seems like a fun time to...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
Sannino's Bella Vita Vineyard
I am in awe that I am the first to review Sannino Bella Vita.... I began a relaxing Sunday afternoon in Long Island Wine Country at Sannino Bella Vita....read more
- bedrooms 3
- community Southold Shores
- rental type House
- sleeps 5
- baths 2
- rates (USD)
$600
- $2,200
/wk
- 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
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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