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

Vacation rentals in Southold

Browse 182 available vacation homes and compared across 7 trusted partners
Anytime
Guests
Anytime
Guests

  • Price per night

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

  • Accommodation types

    • House
    • Farmhouse
    • Apartment

  • Distance to center

    • 2 mi
    • 3 mi
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • 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 182 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Cabin Southold
Cabin ∙ 3 guests ∙ 2 bedrooms

Family-oriented wonderful cottage with BBQ

Southold, Suffolk County, New York, United States
This North Fork cabin features a fireplace, kitchen, beach access, and parking, perfect for a family getaway with three guests.
from $176
per night
Outstanding(1 rating)
from $176
per night
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

House with yard, barbeque & patio | City view

Southold, Suffolk County, New York, United States
This North Fork house rental accommodates 10, featuring a fireplace, kitchen, yard, and parking for an unforgettable getaway.
from $357
per night
Outstanding(21 ratings)
from $357
per night
View deal
House Southold
House ∙ 10 guests ∙ 6 bedrooms

House with barbecue, terrace & jacuzzi | City view

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, hot tub, and a spacious yard, perfect for family gatherings.
from $1,073
per night
Outstanding(45 ratings)
from $1,073
per night
View deal
Cabin Southold
Cabin ∙ 6 guests ∙ 2 bedrooms

Children-friendly cottage with garden, barbecue & terrace | Nature view

Southold, Suffolk County, New York, United States
This North Fork cabin offers a fireplace, kitchen, yard, and waterfront access, perfect for family vacations of up to six.
from $372
per night
Outstanding(106 ratings)
from $372
per night
View deal
Cabin Southold
Cabin ∙ 5 guests ∙ 3 bedrooms

Child-friendly cottage with yard, BBQ & terrace

Southold, Suffolk County, New York, United States
This North Fork cabin features a waterfront yard, a cozy fireplace, and a kitchen, perfect for family getaways of up to 5.
from $400
per night
Outstanding(209 ratings)
from $400
per night
View deal
House Southold
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with terrace, barbeque & private pool

Southold, Suffolk County, New York, United States
This waterfront house rental in North Fork features a private heated pool, kitchen, and a yard, perfect for family gatherings.
from $729
per night
Outstanding(57 ratings)
from $729
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 $797
per night
Outstanding(89 ratings)
from $797
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 $399
per night
Outstanding(30 ratings)
from $399
per night
View deal
Cabin Southold
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with grill, patio & yard

Southold, Suffolk County, New York, United States
This North Fork cabin features a kitchen, fireplace, balcony, and yard, perfect for families and pets seeking adventure.
from $230
per night
Excellent(36 ratings)
from $230
per night
View deal
House Southold
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented house with hot tub, garden & terrace

Southold, Suffolk County, New York, United States
This waterfront house rental in North Fork features a hot tub, fireplace, and balcony, perfect for families seeking adventure.
from $1,018
per night
Outstanding(202 ratings)
from $1,018
per night
View deal
House Southold
House ∙ 4 guests ∙ 2 bedrooms

House with yard & grill | Lake view

Southold, Suffolk County, New York, United States
This waterfront house rental in North Fork features a kitchen, fireplace, and yard, perfect for families and pets.
from $276
per night
Very good(21 ratings)
from $276
per night
View deal
Farmhouse Southold
Farmhouse ∙ 6 guests ∙ 3 bedrooms

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

Southold, Suffolk County, New York, United States
This North Fork farmhouse rental offers beach access, a kitchen, fireplace, and yard, perfect for six guests seeking adventure.
from $252
per night
Outstanding(45 ratings)
from $252
per night
View deal
House Southold
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly vacation home with BBQ, private pool & patio | Suitable for remote work | Pets allowed

Southold, Suffolk County, New York, United States
This North Fork house rental offers a private pool, hot tub, and yard, perfect for family gatherings and pet-friendly fun.
from $764
per night
Outstanding(12 ratings)
from $764
per night
View deal
Cabin Southold
Cabin ∙ 4 guests ∙ 2 bedrooms

Cottage with BBQ, garden & terrace | Nature view

Southold, Suffolk County, New York, United States
This North Fork cabin features a fireplace, kitchen, yard, waterfront access, and parking, perfect for a getaway with friends.
from $187
per night
Outstanding(44 ratings)
from $187
per night
View deal
House Southold
House ∙ 4 guests ∙ 2 bedrooms

House with barbeque | Nature view | Good for workation

Southold, Suffolk County, New York, United States
This North Fork house rental features a kitchen, fireplace, and pet-friendly space, perfect for a family getaway.
from $302
per night
Outstanding(10 ratings)
from $302
per night
View deal

Vacation Houses With Pools

House Southold
from $684
per night
House ∙ 6 guests ∙ 3 bedrooms

House with yard, pool & patio

5.0
Outstanding(15 ratings)
Southold, Suffolk County, New York, United States
Pool
View deal
House Southold
from $490
per night
House ∙ 8 guests ∙ 4 bedrooms

House with private pool, garden & terrace

5.0
Outstanding(3 ratings)
Southold, Suffolk County, New York, United States
Pool
View deal
House Southold
from $715
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
See all offers

Dog-Friendly Vacation Rentals

House Southold
from $309
per night
House ∙ 4 guests ∙ 2 bedrooms

Children-friendly vacation home with garden & patio | Pets are welcome

5.0
Outstanding(7 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $603
per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, grill & yard

5.0
Outstanding(52 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $830
per night
House ∙ 8 guests ∙ 5 bedrooms

Vacation home with terrace, yard & barbeque

5.0
Outstanding(18 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

Cabin Southold
from $262
per night
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with terrace, BBQ & garden | Suitable for remote work

Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $416
per night
House ∙ 8 guests ∙ 4 bedrooms

Children-friendly pleasant house with patio | Good for workation

4.7
Excellent(6 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $1,680
per night
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with terrace, barbeque & garden | Nature view

4.9
Outstanding(12 ratings)
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 $783
per night
House ∙ 6 guests ∙ 3 bedrooms

Fully equipped beautiful house with yard, grill & patio

5.0
Outstanding(8 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $435
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented pleasant vacation home with grill

5.0
Outstanding(2 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $560
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

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 $374
per night
House ∙ 6 guests ∙ 3 bedrooms

House with grill & terrace

4.7
Excellent(35 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $324
per night
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly charming house with terrace, garden & barbeque

4.9
Outstanding(27 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $516
per night
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented wonderful vacation home with terrace, yard & BBQ

5.0
Outstanding(26 ratings)
Southold, Suffolk County, New York, United States
View deal

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Verified reviews

Verified reviews

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

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Price clarity, no surprises

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

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Find your dream stay

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

Popular Features & Amenities in Southold

  • Pet-friendly (69)
  • Pool (72)
  • Air conditioning (175)
  • WiFi (176)
  • Grill (105)
  • TV (145)
  • Washing machine (114)
  • Kitchen (135)
  • Dishwasher (95)
  • Parking (10)
  • No smoking (177)
  • Balcony/patio (143)

Southold is a great vacation destination if you want an accommodation with a pool, as 39% 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 182 rentals
🌙 Nightly prices starting at $185
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 69 homes
🏊 Vacation rentals with pools 71 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 $185 per night. Nightly prices for house rentals are $1,138 on average. Cottages in Southold cost on average $653 per night.

How many vacation rentals are available to book in Southold?

There are currently 182 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 71 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 69 pet-friendly available.

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