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Vacation rentals in Southold

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Top-rated vacation rentals in Southold

Guests agree: these stays are highly rated for location, cleanliness, and more.

Walk to it all! - Eat, Drink, Beach, Shop - Apt #1
SUPERHOST
Entire residential home · 6 guests · 3 beds · 1 bath
Walk to it all! - Eat, Drink, Beach, Shop - Apt #1Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).
Greenport Village View - Walkable 2BR Stay
SUPERHOST
Entire rental unit · 4 guests · 3 beds · 1 bath
Greenport Village View - Walkable 2BR StayLocated in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable.
Greenport Village home w/ POOL! Steps to Beach!
Entire residential home · 13 guests · 6 beds · 2 baths
Greenport Village home w/ POOL! Steps to Beach!Perfect year-round getaway in desirable West Dublin neighborhood of Greenport Village. This 2200 sq ft home is comfortable, spacious, super clean and meticulously landscaped! Sleeps 13 guests comfortably. One of only a handful of homes in the Village of Greenport with a POOL (open from approximately mid-May to mid-September)! This home is a perfect location no matter what your interests are out on the North Fork! The fun and relaxation opportunities are endless!

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Other great vacation rentals in Southold

  1. Entire residential home
  2. Greenport
Greenport Victorian - Location, Location, Location
$200 per night
  1. Entire rental unit
  2. Greenport
The_BoHo_ Bay_ Stay:apt, 3 blocks from Peconic Bay
$300 per night
SUPERHOST
  1. Entire residential home
  2. Greenport
Water Views Beach Greenport Getaway
$675 per night
SUPERHOST
  1. Entire guest suite
  2. Greenport
Village suite w/private entry near the beach
$186 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Greenport
"Breathtaking Waterfront Water's Edge view"
$448 per night
  1. Entire residential home
  2. Southold
CHARMING 5 BEDROOM WITH WATER VIEWS, PRIVATE BEACH
$302 per night
SUPERHOST
  1. Entire residential home
  2. Greenport
Charming Home in the heart of Greenport Village!
$304 per night
  1. Private room
  2. Southold
Cozy guest room - w/ private beach - quiet getaway
$117 per night
SUPERHOST
  1. Entire guest suite
  2. Cutchogue
Walk to Vineyards, Beaches, Farms & Town
$149 per night
SUPERHOST
  1. Entire residential home
  2. Greenport
Large Greenport Village Apartment w/Porch + Office
$241 per night
SUPERHOST
  1. Entire residential home
  2. Greenport
Relaxed Village Farmhouse
$417 per night
SUPERHOST
  1. Entire residential home
  2. Greenport
Luna's Beach Cottage
$549 per night