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Southold summer vacation rentals

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Top-rated vacation rentals in Southold

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

SUPERHOST
  1. Entire cottage
  2. North Fork
Sweet Cottage Charmer

Welcome to my incredibly cozy Southold cottage. Located steps to the Peconic Bay, village of Southold and a short lovely bike ride to the beach. This 2 bedroom 1 bathroom home has all you need for a memorable vacation. We provide discounts for 14 day stays. Please send inquiries for details.

$407 per night
SUPERHOST
  1. Entire rental unit
  2. North Fork
Beach Studio 2

Kick back and relax in this calm, stylish space.Gut renovated sunny studio apartment steps from the beach! All new appliances and amenities. Minimal and chic decor. Large outdoor space. A perfect summer getaway. Close to Greenport and wine country.

$311 per night
SUPERHOST
  1. Entire guest suite
  2. North Fork
Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed by me for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact. Less than five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Bhavana Blueberry farm, Erik’s restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard, and Love Lane.

$250 per night

Vacation rentals for every style

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Southold vacation rentals

  1. Entire guesthouse
  2. North Fork
Southold- Adorable 1 Bedroom Cottage
$328 per night
  1. Entire home
  2. North Fork
North Fork Lakefront cottage near Kenney's beach
$290 per night
  1. Private room
  2. North Fork
Cozy guest room - w/ private beach - quiet getaway
$174 per night
SUPERHOST
  1. Entire guest suite
  2. North Fork
Walk to Vineyards, Beaches, Farms & Town
$206 per night
SUPERHOST
  1. Entire rental unit
  2. North Fork
Bright, Southold Studio Apt near beach & town
$255 per night
  1. Entire cottage
  2. North Fork
Cozy & Bright Beachside Cottage
$468 per night
  1. Entire home
  2. North Fork
Amazing Beach House in the North Fork Wineries
$425 per night
SUPERHOST
  1. Private room
  2. North Fork
A Country House Bed and Breakfast in Wine Country
$250 per night
  1. Entire home
  2. North Fork
Greenport Victorian - Location, Location, Location
$215 per night
SUPERHOST
  1. Entire home
  2. North Fork
Walk to it all! - Eat, Drink, Beach, Shop - Apt #1
$385 per night
SUPERHOST
  1. Entire guest suite
  2. North Fork
Village suite w/private entry near the beach
$282 per night
SUPERHOST
  1. Entire cottage
  2. North Fork
Southold Cottage on Beach-Great 4 remote work too!
$346 per night

Southold beach vacation rentals

SUPERHOST
  1. Entire cottage
  2. North Fork
Little Whale House | Charming Greenport Cottage
$330 per night
SUPERHOST
  1. Entire rental unit
  2. North Fork
The_BoHo_ Bay_ Stay:apt, 3 blocks from Peconic Bay
$382 per night
SUPERHOST
  1. Entire guest suite
  2. North Fork
Enjoy a relaxing getaway to the North Fork
$196 per night
SUPERHOST
  1. Entire rental unit
  2. North Fork
Greenport Village View - Walkable 2BR Stay
$356 per night
SUPERHOST
  1. Entire home
  2. North Fork
Summer Retreat at the beach , enjoy Wine Country
$500 per night
  1. Entire rental unit
  2. North Fork
Evolve | 2nd-Floor Apt 1/2 Mi to Greenport Harbor!
$225 per night
  1. Entire condo
  2. North Fork
Beachside Water View Condo with Pool in Greenport
$400 per night
  1. Entire rental unit
  2. North Fork
Junior 1-BR in the heart of Greenport Village
$367 per night
  1. Entire home
  2. North Fork
Water & Vineyard views, 4 bedrooms
$567 per night
  1. Entire home
  2. North Fork
Lake House Near Beaches and North Fork Wineries
$350 per night
  1. Entire cottage
  2. North Fork
Lovely 2 BR Beach House No. Shore
$151 per night
  1. Entire home
  2. North Fork
Views of Corey Creek on a quiet peninsula
$420 per night
  1. Airbnb
  2. United States
  3. New York
  4. Suffolk County
  5. Southold