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Vacations by Zumper

Vacation Rentals in Southold, NY

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Southold, NY

Book a vacation rental in Southold that has the highest visitor rating. Here are 6 of the best vacation rentals in Southold.
Price drop
Bright Oasis in the Heart of North Fork Wine Country
10

Excellent

·
Southold
·
4 br
·
Sleeps 8
·
Residents Lounge · Dishwasher · Workspace ·
From
$507/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Residents Lounge
Dishwasher
Wifi
In Unit Laundry
Air Conditioning
Fitness Center
Furnished
Beach
Other spaces
Workspace, Kitchen
Price drop
Entire Loft-Walk to Town, Beach, Train, Wine Trail
10

Excellent

·
Southold
·
Studio
·
Sleeps 4
·
Outdoor Space · Storage · Oven ·
From
$252/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Storage
Oven
In Unit Laundry
Furnished
Dishwasher
Air Conditioning
Wifi
Other spaces
Kitchen, Workspace
Price drop
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
10

Excellent

·
Southold
·
2 br
·
Sleeps 4
·
Beach · In Unit Laundry · Oven ·
From
$333/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Beach
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
North Beach Fork Beach House
10

Excellent

·
Southold
·
3 br
·
Sleeps 6
·
Dishwasher · Outdoor Space · Fireplace ·
From
$344/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Fireplace
Wifi
Fitness Center
Oven
Residents Lounge
In Unit Laundry
Air Conditioning
Other spaces
Kitchen, Deck
Price drop
Steve's Place: Heated Pool, 3BR Southold Home, Beach
10

Excellent

·
Southold
·
3 br
·
Sleeps 6
·
Fitness Center · Swimming Pool · Fireplace ·
From
$458/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Swimming Pool
Fireplace
In Unit Laundry
Garage Parking
Air Conditioning
Beach
Dishwasher
Other spaces
Kitchen, Workspace
Southold Sanctuary - North Fork Getaway
10

Excellent

·
Southold
·
4 br
·
Sleeps 8
·
Air Conditioning · Furnished · Wifi ·
From
$699/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Furnished
Wifi
In Unit Laundry
Oven
Dishwasher
Residents Lounge
Other spaces
Kitchen, Workspace

Budget-Friendly Vacation Rentals in Southold, NY

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Southold starting at $127. Use the price filter at the top of the page to search for more specific prices.
Price drop
Sweet Southold Beach Cottage FALL WINTER SUMMER
10

Excellent

·
Southold
·
2 br
·
Sleeps 2
·
Outdoor Space · Furnished · Package Service ·
From
$127/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Furnished
Package Service
Hot Tub
Wifi
In Unit Laundry
Beach
Ceiling Fan
On Site Laundry
Other spaces
Kitchen
Price drop
Southold Cottage w/ Patio & Grill - Walk to Beach!

No rating

·
Southold
·
2 br
·
Sleeps 3
·
Ceiling Fan · Outdoor Space · Air Conditioning ·
From
$133/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Ceiling Fan
Air Conditioning
Oven
Fireplace
In Unit Laundry
Beach
Furnished
Wifi
Other spaces
Kitchen, Workspace
Price drop
A Natural Getaway
10

Excellent

·
Southold
·
3 br
·
Sleeps 6
·
Dishwasher · Outdoor Space · Oven ·
From
$180/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Furnished
Residents Lounge
Air Conditioning
Wifi
Beach
Other spaces
Kitchen, Workspace
Price drop
Beautiful garden-view home near the water with lawn, streaming, W/D, AC, kitchen
10

Excellent

·
Southold
·
2 br
·
Sleeps 4
·
Outdoor Space · Workspace · Furnished ·
From
$186/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Furnished
Free Parking
Air Conditioning
Oven
In Unit Laundry
Dishwasher
Other spaces
Workspace, Kitchen
Price drop
The Stucco House

No rating

·
Southold
·
3 br
·
Sleeps 6
·
Dishwasher · In Unit Laundry · Kitchen ·
From
$193/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Fireplace
Furnished
Wifi
Oven
Air Conditioning
Other spaces
Kitchen, Workspace
Price drop
Charming home with fireplace, kayaks, patio, fast WiFi, & washer/dryer-dogs ok
10

Excellent

·
Southold
·
1 br
·
Sleeps 4
·
Free Parking · Dishwasher · In Unit Laundry ·
From
$194/night
Check availability
Property
House · 1 Bed · 2 baths
Amenities
Free Parking
Dishwasher
In Unit Laundry
Furnished
Fireplace
Oven
Air Conditioning
Other spaces
Kitchen
Expand your search criteria to see more vacation rentals near Southold.
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Updated: October 1, 2023