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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

 

Sparkling Pointe

Sparlking Pointe is more or less an outlier in LI's wine region. They only do one thing - the bubbly. Like many of LI's wineries, it certainly is...read more

 

One Woman Wines & Vineyard

By far our FAVORITE stop of the day. We had a great time talking to the people behind the counter. Can't wait to enjoy the wines we brought home from here.read more

 

Raphael Vineyard and Winery

Raphael Winery is hands down my favorite on the North Fork! We have gone there several times and we are never disappointed. The wines are delicious and it...read more

 

McCall Wines

Love it! This was the first stop for my bachelorette wine tour and It was so nice and the wine was so good I ended up going back again. It is in the small...read more

 

Sannino's Bella Vita Vineyard

This was the second stop on our wine tour and we opted to have the Vine to Wine tour, which includes about 5 tastings and taught us all about the wine...read more

 

Croteaux Vineyards

It's like walking onto the set of a movie. Suddenly I feel like I'm in a scene from under the tuscan sun and it's pretty amazing. They don't allow the mega...read more

 

Mattebella Vineyards

Yay for you for finding this review! It means you will know about a hidden gem on the North Fork - Mattebella! Have been going here for years (after...read more

 

Pindar Vineyards

As someone who has been a wine enthusiast for years, I can confidently say that this was the worst wine I have ever had in my life. Worse than Barefoot, or...read more

 

The Lenz Winery

We were here for about an hour while on a wine tour that hit up 3 vineyards. We arrived late so we didn't get to do anything other than sample 4 wines in...read more

 

Duck Walk Vineyards

The place is clean which is what made the review 3 stars. I wish I could even rate it a 2.5. They didn't have our reservation written down, but accommodated...read more

 

Lieb Cellars

We have been to many wineries in the North Fork over the years, but this was our first visit to Lieb. We went to the location on Oregon Road in Cutchoge....read more

 

The Winemaker Studio

This is a nice little find. It was described to us that the local winemakers make a variety of wines that are not traditionally marketed. We had one...read more

 

Kontokosta Winery

This winery is absolutely breathtaking. After going up a long driveway, you'll see their red barn door. The two level tasting room is very sleek and...read more

 

Shinn Estate Vineyards

*Sigh* Unfortunately, I need to join the ranks of those who think that this place is awesome.... until you encounter the owners. Went there with my...read more

 

Castello di Borghese Vineyard & Winery

My friends and I ended up here accidentally around November 2013. The staff was so friendly and eager to make sure we were having a wonderful time. I'm...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
 
 
 
 
 

56 reviews write a review

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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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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March April WEEKNIGHTS $275: 100 acres, water pool golf gourmet kitchen
Southold House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $250 - $1,714 /nt
    $6,000 - $12,000 /wk
 
 
 
 
 

126 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 - $599 /nt
    $2,800 - $4,800 /wk
 
 
 
 
 

3 reviews write a review

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
 
 
 
 
 

11 reviews write a review

Restful Retreat, all new renovation, near Beaches and North Fork Wineries
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $375 - $395 /nt
    $2,100 - $3,200 /wk
 
 
 
 
 

6 reviews write a review

Lighthouse Inspired Lakefront Beach House, Overlooking LI Sound
Southold House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $257 - $357 /nt
    $1,800 - $2,500 /wk
    $6,000 - $9,500 /mth
 
 
 
 
 

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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
 
 
 
 
 

12 reviews write a review

Walk barefoot to the beach...
Southold Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $400 - $600 /nt
    $1,050 - $2,500 /wk
    $3,000 - $7,500 /mth
 
 
 
 
 

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