Search Villas in Southold

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare Villas in Southold with updated reviews, rates, and availability.

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (151)
"Love love love this place ! Can’t say enough "
The price is SAR 635
SAR 726 total
includes taxes & fees
31 Mar - 1 Apr
The Shoals Suites and Slips

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand

White Blossom House Inn

2.5 star property
10.0 out of 10, Exceptional, (6)
"Charming and cozy. Lovely outside sitting areas."
White Blossom House Inn

Cozy Long Island Escape

10.0 out of 10, Exceptional, (2)
"Big house, lots of room for a family gathering. Mary was super friendly and accommodating. "
Cozy Long Island Escape

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Shorecrest Bed and Breakfast

3.5 star property
9.8 out of 10, Exceptional, (18)
"We had a really nice, two night stay! The breakfasts were delicious and accommodations were really nice!"
Shorecrest Bed and Breakfast

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Southold
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"We were in town for a wedding with small children in tow- the house was perfectly located for us to get to wedding events in under 10 minutes but do be aware that it’s on a busy road. The house is set back so there wasn’t too much traffic noise, especially with the window AC units going. You could walk to the beach, but be aware that it’s down the busy road as someone else mentioned. It wasn’t luxurious, but everything was clean and comfortable. I appreciated that towels and linens were provided...
North Fork 7 Bedroom Farmhouse Escape

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"Great cozy place"
The price is SAR 494
SAR 646 total
includes taxes & fees
12 Mar - 13 Mar
Windward Shores Ocean Resort

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
The price is SAR 650
SAR 906 total
includes taxes & fees
25 Mar - 26 Mar
Cliffside Resort Condominiums
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your villa in Southold with Expedia?
We think organizing a vacation shouldn’t be complicated, so if you’re in search of villas at a nice price, Expedia has you covered. Stick to the budget and opt for an all-inclusive stay, or splurge on a luxury villa to treat your sweetheart. Our search filters make it simple to secure a property in Southold that suits your needs.
How can I find cheap villas in Southold?
With Expedia’s convenient filter tool, sourcing cheap villas in Southold is a cinch. To discover stays that are gentle on your bank balance, narrow your search by budget, star rating and amenities.