Vacation rentals in Southold - HomeToGo base64Hash Vacation rentals in Southold - HomeToGo

Vacation rentals in Southold

Browse 190 available vacation homes and compared across 8 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • House
    • Farmhouse
    • Apartment

  • Distance to center

    • 1 mi
    • 2 mi
    • 3 mi

  • Rating

    • 4.5+
    • 4+

  • Services

    • Pool
    • Air conditioning
    • WiFi
    • TV
    • Washing machine
    • Kitchen
    • Dishwasher
    • Parking
    • Balcony/patio
    • Microwave
    • Yard
    • Fireplace
    • Crib
    • Hot tub
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • Wheelchair access
    • No pets

  • Activities

    • Grill
    • Fishing

Top 15 most Recommended Vacation Rentals in Southold

Discover your ideal Southold vacation rental with real-time comparisons of 190 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Southold
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with terrace & grill

Southold, Suffolk County, New York, United States
This North Fork house rental offers a fireplace, kitchen, parking, and pet-friendly space, perfect for six guests.
from $564
per night
Outstanding(11 ratings)
from $564
per night
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, BBQ & garden | Nature view | Suitable for remote work

Southold, Suffolk County, New York, United States
This North Fork house rental features a yard, balcony, and fireplace, perfect for families and pets, accommodating up to six guests.
from $507
per night
Outstanding(12 ratings)
from $507
per night
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful house with yard, grill & patio

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, fireplace, kitchen, yard, and parking for six guests.
from $774
per night
Outstanding(8 ratings)
from $774
per night
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

Children-friendly wonderful house with patio, hot tub & BBQ | Nature view

Southold, Suffolk County, New York, United States
This North Fork house rental offers a waterfront retreat with a hot tub, fireplace, and ample space for family gatherings.
from $502
per night
Outstanding(10 ratings)
from $502
per night
View deal
House Southold
House ∙ 8 guests ∙ 4 bedrooms

House with private pool, garden & terrace

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, a cozy fireplace, and ample outdoor space for eight guests.
from $586
per night
Outstanding(4 ratings)
from $586
per night
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

Pleasant vacation home with garden | Nature view

Southold, Suffolk County, New York, United States
This North Fork house rental features a fireplace, kitchen, parking, beach access, and stunning waterfront views for 10 guests.
from $739
per night
Outstanding(38 ratings)
from $739
per night
View deal
House Southold
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented pleasant house with garden, barbecue & terrace | Perfect for remote work | Pet-friendly

Southold, Suffolk County, New York, United States
This North Fork house rental offers beach access, a waterfront yard, and a family-friendly kitchen, accommodating up to 10 guests.
from $1,649
per night
Outstanding(20 ratings)
from $1,649
per night
View deal
House Southold
House ∙ 10 guests ∙ 6 bedrooms

House with garden, barbecue & terrace

Southold, Suffolk County, New York, United States
This North Fork house rental features beach access, waterfront views, a yard, and a fireplace, perfect for 10 guests and pets.
from $592
per night
Outstanding(2 ratings)
from $592
per night
View deal
House Southold
House ∙ 8 guests ∙ 5 bedrooms

Vacation home with terrace, yard & barbeque

Southold, Suffolk County, New York, United States
This North Fork house rental offers waterfront access, a yard, and a balcony, perfect for families and pets alike.
from $834
per night
Outstanding(18 ratings)
from $834
per night
View deal
House Southold
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with private pool, grill & garden

Southold, Suffolk County, New York, United States
This house rental in North Fork features a private heated pool, yard, and fireplace, perfect for family gatherings of 10.
from $816
per night
Outstanding(89 ratings)
from $816
per night
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

Family-oriented spacious vacation home with barbeque, yard & terrace | Suitable for remote work | Pets allowed

Southold, Suffolk County, New York, United States
This North Fork house rental offers a private heated pool, fireplace, kitchen, and space for 10, perfect for family getaways.
from $551
per night
Outstanding(8 ratings)
from $551
per night
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly charming house with grill, terrace & yard

Southold, Suffolk County, New York, United States
This North Fork house rental features a fireplace, kitchen, yard, and parking, perfect for families seeking a memorable getaway.
from $390
per night
Outstanding(50 ratings)
from $390
per night
View deal
House Southold
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped nice house with BBQ, garden & terrace | Pet-friendly

Southold, Suffolk County, New York, United States
This waterfront house rental on North Fork offers beach access, a yard, and a balcony, perfect for gatherings of up to eight.
from $407
per night
Outstanding(30 ratings)
from $407
per night
View deal
House Southold
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly nice vacation home with garden, terrace & private pool | Nature view | Suitable for remote work | Pets allowed

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, yard, and space for up to 8 guests, perfect for family getaways.
from $1,172
per night
Outstanding(39 ratings)
from $1,172
per night
View deal
House Southold
House ∙ 7 guests ∙ 3 bedrooms

Family-oriented beautiful vacation home with BBQ, patio & private pool | Nature view | Suitable for remote work

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, waterfront access, and a family-friendly yard for unforgettable vacations.
from $647
per night
Outstanding(34 ratings)
from $647
per night
View deal

Vacation Houses With Pools

House Southold
from $268
per night
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, yard & barbeque

Southold, Suffolk County, New York, United States
Pool
View deal
House Southold
from $749
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-friendly house with yard, terrace & private pool | Good for workation

4.8
Outstanding(20 ratings)
Southold, Suffolk County, New York, United States
Pool
View deal
House Southold
from $627
per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, pool & patio

5.0
Outstanding(16 ratings)
Southold, Suffolk County, New York, United States
Pool
View deal
See all offers

Dog-Friendly Vacation Rentals

House Southold
from $632
per night
House ∙ 6 guests ∙ 3 bedrooms

House with grill, garden & terrace | Nature view | Perfect for remote work

5.0
Outstanding(59 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $410
per night
House ∙ 6 guests ∙ 3 bedrooms

House with private pool, grill & yard

5.0
Outstanding(12 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $555
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, barbeque & garden | Nature view | Good for workation

5.0
Outstanding(5 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

Cabin Southold
from $233
per night
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with grill, patio & yard

4.7
Excellent(36 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $1,291
per night
House ∙ 12 guests ∙ 8 bedrooms

Vacation home with private pool, terrace & garden | Good for workation

5.0
Outstanding(20 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $1,137
per night
House ∙ 8 guests ∙ 3 bedrooms

Family-friendly charming house with barbeque, yard & patio | Dogs allowed

Southold, Suffolk County, New York, United States
Balcony
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Southold offering exceptional value for money

House Southold
from $613
per night
House ∙ 7 guests ∙ 3 bedrooms

Fully equipped nice house with yard & barbecue | Lake view

5.0
Outstanding(12 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $379
per night
House ∙ 6 guests ∙ 3 bedrooms

House with garden, barbecue & terrace | Nature view | Good for workation

5.0
Outstanding(26 ratings)
Southold, Suffolk County, New York, United States
View deal
Cabin Southold
from $938
per night
Cabin ∙ 8 guests ∙ 3 bedrooms

Cottage with BBQ & terrace | Nature view

5.0
Outstanding(40 ratings)
Southold, Suffolk County, New York, United States
View deal

Top-Rated Vacation rentals in Southold

Book the highest-rated Southold vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Southold
from $864
per night
House ∙ 6 guests ∙ 4 bedrooms

Child-friendly house with barbecue, patio & garden | Good for workation

4.9
Outstanding(33 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $704
per night
House ∙ 10 guests ∙ 4 bedrooms

House with yard, terrace & BBQ | Suitable for remote work

5.0
Outstanding(29 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $611
per night
House ∙ 7 guests ∙ 4 bedrooms

Family-oriented house with garden, grill & terrace | Nature view | Perfect for remote work | Pet-friendly

5.0
Outstanding(23 ratings)
Southold, Suffolk County, New York, United States
View deal

Why choose HomeToGo?

Securely pay and stay your way

Securely pay and stay your way

Choose local, trusted payment methods, plus trip insurance and add-on services.

Award-winning customer service

Award-winning customer service

Experience seamless, hands-on support for any booking questions or concerns.

Verified reviews

Verified reviews

Trust in the quality and comfort of your stay with verified guest reviews.

Price clarity, no surprises

Price clarity, no surprises

Spend your budget exactly as planned by comparing thousands of providers.

Smart search made simple

Smart search made simple

Transform vacation planning into a joy with advanced, AI-powered search tools.

Find your dream stay

Find your dream stay

Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Features & Amenities in Southold

  • Pet-friendly (71)
  • Pool (72)
  • Air conditioning (179)
  • WiFi (180)
  • Grill (108)
  • TV (149)
  • Washing machine (118)
  • Kitchen (139)
  • Dishwasher (98)
  • Parking (11)
  • No smoking (181)
  • Balcony/patio (144)

Southold is a great vacation destination if you want an accommodation with a pool, as 40% of the offers have one. Also, more House rental have pools than any other property type. They are a great choice if you go in a group of 4, as that is the number of people they can accommodate on average. You can also rent a rental providing a pool near the water, which is the case for one-third of the rentals there.

Information about vacation rentals in Southold

🏡 Vacation rentals available 190 rentals
🌙 Nightly prices starting at $184
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 74 homes
🏊 Vacation rentals with pools 76 homes

Frequently Asked Questions

What is the average price per night for a vacation home in Southold?

On average, vacation rentals in Southold cost around $184 per night. Nightly prices for house rentals are $1,137 on average. Cottages in Southold cost on average $673 per night.

How many vacation rentals are available to book in Southold?

There are currently 190 rentals to choose from for your trip.

What are the most popular amenities for vacation rentals in Southold?

If you're looking to book a vacation rental in Southold, travelers search for vacation homes with Pets allowed, Pool and Air conditioning.

How many vacation homes with pools are in Southold?

Southold offers 76 Hotel room and Cabin options available for renting.

Are dogs allowed in vacation homes in Southold?

Finding a vacation home in Southold that allows pets is easy, with 74 pet-friendly available.

Top cities to visit

Most Popular Destinations

Show more
image-tag