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

Vacation rentals in Southold

Browse 33 available vacation homes and compared across 5 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+

  • Popular amenities

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

  • Other Services

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

Bed and breakfast Southold
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with patio, yard & jacuzzi

Southold, Suffolk County, New York, United States
This Southold bed and breakfast offers a heated pool, hot tub, and cozy fireplace, perfect for a relaxing getaway for two.
from $550
per night
Outstanding(2 ratings)
from $550
per night
View deal
Bed and breakfast Southold
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Charming bed and breakfast with pool, terrace & garden | Nature view

Southold, Suffolk County, New York, United States
This Southold bed and breakfast offers beach access, a pool, and a cozy fireplace, perfect for a relaxing getaway for two.
from $589
per night
Outstanding(20 ratings)
from $589
per night
View deal
Bed and breakfast Southold
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed and breakfast with yard, patio & pool | Nature view

Southold, Suffolk County, New York, United States
This Southold bed and breakfast features a pool, fireplace, yard, and beach access, perfect for a romantic getaway for two.
from $589
per night
Outstanding(20 ratings)
from $589
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 $566
per night
Outstanding(3 ratings)
from $566
per night
View deal
House Southold
House ∙ 12 guests ∙ 5 bedrooms

Family-friendly lovely vacation home with yard, private pool & barbeque | Suitable for remote work | Pets are welcome

Southold, Suffolk County, New York, United States
This North Sea house rental features a private heated pool, yard, and kitchen, perfect for family gatherings and pet-friendly stays.
from $491
per night
Outstanding(35 ratings)
from $491
per night
View deal
House Southold
House ∙ 13 guests ∙ 6 bedrooms

Child-friendly wonderful vacation home with private pool, barbeque & yard | Perfect for remote work | Dogs allowed

Southold, Suffolk County, New York, United States
This North Fork house rental features a private heated pool, spacious yard, and family-friendly amenities for up to 13 guests.
from $1,387
per night
Outstanding(44 ratings)
from $1,387
per night
View deal
Cabin Southold
Cabin ∙ 6 guests ∙ 3 bedrooms

Cottage with yard, barbecue & terrace | Nature view

Southold, Suffolk County, New York, United States
This waterfront cabin in Orient offers beach access, a fireplace, and a yard, perfect for up to six guests with pets.
from $247
per night
Outstanding(34 ratings)
from $247
per night
View deal
House Southold
House ∙ 8 guests ∙ 3 bedrooms

Vacation home with patio, private pool & grill | Nature view

Southold, Suffolk County, New York, United States
This North Fork farmhouse rental features a private heated pool, a kitchen for family meals, and a spacious yard for pets.
from $282
per night
Outstanding(29 ratings)
from $282
per night
View deal
House Southold
House ∙ 7 guests ∙ 4 bedrooms

Vacation home with patio, yard & barbeque | Lake view

Southold, Suffolk County, New York, United States
This house rental in North Sea offers waterfront access, a kitchen, and a yard with lake views, perfect for family getaways.
from $702
per night
Outstanding(32 ratings)
from $702
per night
View deal
Cabin Southold
Cabin ∙ 4 guests ∙ 3 bedrooms

Family-oriented cottage with terrace & BBQ | Suitable for remote work | Pets allowed

Southold, Suffolk County, New York, United States
This waterfront cabin on North Fork offers beach access, a kitchen, and pet-friendly amenities for a perfect family getaway.
from $93
per night
Outstanding(102 ratings)
from $93
per night
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

Children-friendly charming house with grill, terrace & yard | Nature view

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 $384
per night
Excellent(50 ratings)
from $384
per night
View deal
House Southold
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with grill, yard & jacuzzi | Good for workation

Southold, Suffolk County, New York, United States
This North Fork house rental features a yard, fireplace, and kitchen, making it ideal for family gatherings and pet-friendly fun.
from $544
per night
Outstanding(30 ratings)
from $544
per night
View deal
House Southold
House ∙ 6 guests ∙ 2 bedrooms

Family-friendly lovely house with BBQ, patio & yard | Nature view | Good for workation | Pets are welcome

Southold, Suffolk County, New York, United States
This North Fork house rental features a yard, fireplace, and kitchen, accommodating up to six guests and pets for a memorable stay.
from $225
per night
Outstanding(54 ratings)
from $225
per night
View deal
House Southold
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly vacation home with grill & pool

Southold, Suffolk County, New York, United States
This North Fork house rental features a pool, kitchen, and parking, perfect for a family getaway with space for 8 guests.
from $571
per night
Outstanding(35 ratings)
from $571
per night
View deal
House Southold
House ∙ 6 guests ∙ 3 bedrooms

House with jacuzzi, yard & patio | Nature view | Good for workation

Southold, Suffolk County, New York, United States
This Shelter Island Heights house rental features a private heated pool, hot tub, and ample space for family fun in the yard.
from $466
per night
Outstanding(53 ratings)
from $466
per night
View deal

Dog-Friendly Vacation Rentals

House Southold
from $852
per night
House ∙ 9 guests ∙ 5 bedrooms

Vacation home with sauna, terrace & private pool

4.6
Excellent(42 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $964
per night
House ∙ 16 guests ∙ 5 bedrooms

House with barbeque & pool

5.0
Outstanding(9 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
House Southold
from $569
per night
House ∙ 10 guests ∙ 4 bedrooms

House with garden, patio & private pool

5.0
Outstanding(32 ratings)
Southold, Suffolk County, New York, United States
Pet-friendly
View deal
See all offers

Vacation rentals with a balcony

House Southold
from $217
per night
House ∙ 4 guests ∙ 1 bedroom

House with grill & yard

5.0
Outstanding(2 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $1,090
per night
House ∙ 6 guests ∙ 3 bedrooms

House with grill & yard | Lake view

4.9
Outstanding(27 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
House Southold
from $839
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with private pool, yard & patio

5.0
Outstanding(50 ratings)
Southold, Suffolk County, New York, United States
Balcony
View deal
See all offers

Vacation houses with Balconies or Patios

House Southold
from $452
per night
House ∙ 6 guests ∙ 3 bedrooms

House with terrace, yard & barbeque | Nature view

4.8
Outstanding(24 ratings)
Southold, Suffolk County, New York, United States
Balcony/Patio
View deal
House Southold
from $388
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
Balcony/Patio
View deal
House Southold
from $378
per night
House ∙ 6 guests ∙ 4 bedrooms

Fully equipped house with BBQ, terrace & yard

5.0
Outstanding(4 ratings)
Southold, Suffolk County, New York, United States
Balcony/Patio
View deal
See all offers

Budget-friendly rental options

Enjoy affordable vacation rentals in Southold offering exceptional value for money

Bed and breakfast Southold
from $549
per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom

Bed & breakfast with garden, patio & pool | Nature view

4.9
Outstanding(20 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $1,326
per night
House ∙ 8 guests ∙ 4 bedrooms

House with yard, grill & private pool | Nature view | Perfect for remote work

4.9
Outstanding(22 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $835
per night
House ∙ 10 guests ∙ 5 bedrooms

Family-oriented house with yard, private pool & grill | Perfect for remote work

4.9
Outstanding(18 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 $1,020
per night
House ∙ 9 guests ∙ 6 bedrooms

House with yard, heated pool & hot tub | Nature view

4.9
Outstanding(157 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $1,072
per night
House ∙ 12 guests ∙ 7 bedrooms

House with barbecue, terrace & jacuzzi | City view

5.0
Outstanding(47 ratings)
Southold, Suffolk County, New York, United States
View deal
House Southold
from $613
per night
House ∙ 8 guests ∙ 3 bedrooms

House with private pool, garden & barbeque

5.0
Outstanding(27 ratings)
Southold, Suffolk County, New York, United States
View deal

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Verified reviews

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

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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 64% of the offers have one. Also, more Bed and breakfast 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 a few of the rentals there.

Information about vacation rentals in Southold

🏡 Vacation rentals available 33 rentals
🌙 Nightly prices starting at $93
⭐ Popular amenities Pets allowed, Pool and Air conditioning
🐾 Pet friendly homes 2 homes
🏊 Vacation rentals with pools 21 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 $93 per night. Nightly prices for bed and breakfast rentals are $698 on average. Cottages in Southold cost on average $723 per night.

How many vacation rentals are available to book in Southold?

There are currently 33 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 21 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 2 pet-friendly available.

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