Help on Feeds

Vacation Rentals in Southold, New York

about Southold

We feature rental homes, villas, cabins, cottages, and condos in destinations all over the world. If you're looking for Southold, New York vacation rentals, click the "rental results" tab and inquire about your favorite listings. Browse Southold vacation deals, family-friendly amenities, and more. If you can't find what you're looking for, remember that vacation rentals in Southold, New York are added and updated every week, so please bookmark us and come back for a visit! Feel free to peruse other destinations as well, as we've got everything from large family vacation rentals to lake cabins to luxury beach houses.

Southold, New York Vacation Rentals and Tourism

more destinations

Check out more areas which feature homes, villas, cabins, cottages, or condos.

Southold things to do

 

Sparkling Pointe

We really enjoyed our visit to Sparkling Pointe. The space is modern, clean, elegant - a bit of Rio or upscale Carribean in the middle of the north fork....read more

 

Duck Walk Vineyards

This is a great winery for a tasting. I've been to both Duck Walk Vineyards and they both have nice tasting rooms. It's true, when it's busy, it's...read more

 

One Woman Wines & Vineyard

We adored this rustic barn for a tasting room. The day we tasted, there was an event including gratis warm food (the ratatouille was absolutely amazing),...read more

 

Corey Creek Winery

I worked here for a summer and when I graduated high school we had a glorious picnic celebration here. It's just that kind of place, a dreamy Euro-vision...read more

 

Croteaux Vineyards

Thanks for the great reviews from everyone. And, as for the not-so-great, we appreciate your feedback and welcome you back for an improved experience.read more

 

Old Field Vineyards

This place looked very beautiful, but we never got to experience the wine-tasting. The samples of wine, the size of a shot, cost $4 each. A full glass was...read more

 

Alure Restaurant

Bring a fly swatter. You'll need it with all flies and bugs crawling and flying around. I came here over the summer with a few friends on a bad stormy...read more

 

Macari Vineyards

Macari is one of the bigger names in the area and put Mattituck on the wine map. I was a little skeptical back in the day but then I visited the tasting...read more

 

Shinn Estate Vineyards

I've been to Shinn several times and I'm 50 / 50 on their wines. Some I like, some I don't...I always bring friends to Shinn whenever I'm doing a tour of...read more

 

Pindar Vineyards

First stop on a recent wine tasting tour. - laid back & cozy vibe - friendly staff - large selection of tastings - i enjoyed the winter white & reisling...read more

 

South Ferry Company

Gets done what needs to be done.read more

 

McCall Wines

You can tell at a glance that this place is the real deal. After you sit in a barn stall and sample some of the best wines LI has to offer, all doubt is...read more

 

Duckwalk Vineyards

I love Duckwalk for what it is; convenient to my grandparents home in Watermill, inexpensive wine tastings (that never seem to stop) and a lovely outdoor...read more

 

Osprey's Dominion Vineyards

I just had a 2008 Oak-barrel Chardonnay from Osprey's Dominion, which I bought at a local liquor store for under 10 dollars. That's kind of unheard of,...read more

 

The Lenz Winery

This might have been our favorite winery on the North Fork. The tasting room is in a lovely potato barn from the 1920's, with high ceilings and good light....read more

powered by:
rental results

availability


Weekly rate:

Min $0, Max $4000

$0
$2,000
$4,000+

Bedrooms: Min 0, Max 5

0
5+







Property Type:


legend

savings
freebies
has photos
has calendar
has swimming pool
has hot tub
pets allowed
owner badge

* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Wine Country Beach House
Southold House Rental Picture
  • House Rental Deals and Discounts $25 off = $275 per night
  • House Rental Deals and Specials Bottle local wine and comp wine tasting... ($30)
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $228 - $350 /nt
    $1,600 - $2,400 /wk
 
 
 
 
 

11 reviews write a review

North Fork Beach House
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $650 - $2,200 /wk
    $3,900 - $7,700 /mth
 
 
 
 
 

write a review

North Fork Lake House
Southold House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $800 - $900 /nt
    $2,800 - $3,200 /wk
    $11,200 - $12,800 /mth
 
 
 
 
 

write a review

Beach House
Southold House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 7
  • baths
  • rates (USD) $600 - $2,500 /wk
    $2,500 - $8,500 /mth
 
 
 
 
 

write a review