Photo by Benny Goh

Search Villas in Southold

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Villas in Southold

No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

Front of property
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 star property
Southold
9.6 out of 10, Exceptional, (221)
"Great quick stay"
United States
Jasmine T
The price is AED 606
AED 784 total
includes taxes & fees
21 Nov - 22 Nov
The Shoals Suites and Slips
Exterior
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveler
The price is AED 2,204
AED 4,314 total
includes taxes & fees
24 Nov - 25 Nov
Beautifully farmhouse
Front of property
Spark by Hilton Guilford

Spark by Hilton Guilford

2.5 star property
Guilford
8.8 out of 10, Excellent, (58)
"Good clean property with great staff "
United States
David
The price is AED 344
AED 395 total
includes taxes & fees
12 Dec - 13 Dec
Spark by Hilton Guilford
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is AED 383
AED 617 total
includes taxes & fees
21 Dec - 22 Dec
The Harbor Front Inn
Property grounds
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (437)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is AED 377
AED 487 total
includes taxes & fees
21 Nov - 22 Nov
Hamlet Inn
Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is AED 716
AED 818 total
includes taxes & fees
23 Nov - 24 Nov
North Fork Cottages & RV Resort
Exterior
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is AED 279
AED 710 total
includes taxes & fees
21 Nov - 22 Nov
The Stern at Soundview · Beach+Ocean+Sunrise
Exterior
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1000)
"Always a great stay at Pier Blue. Comfy bed and plenty of room."
United States
Patricia
Pier Blue Inn Old Saybrook - Essex
Front of property
The Captain Stannard

The Captain Stannard

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (256)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The price is AED 588
AED 653 total
includes taxes & fees
24 Nov - 25 Nov
The Captain Stannard
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (382)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is AED 438
AED 504 total
includes taxes & fees
1 Dec - 2 Dec
The Bentley Hotel Southampton
Exterior
Clinton Motel

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (293)
"Great staff and clean rooms"
United States
Tyler
The price is AED 286
AED 329 total
includes taxes & fees
30 Nov - 1 Dec
Clinton Motel
Front of property
Westbrook Inn B&B

Westbrook Inn B&B

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is AED 525
AED 583 total
includes taxes & fees
1 Dec - 2 Dec
Westbrook Inn B&B
Property entrance
The Niantic Inn

The Niantic Inn

2.5 star property
Niantic
9.0 out of 10, Wonderful, (121)
"Great location. Nice and clean room and property"
United States
Eric
The price is AED 423
AED 487 total
includes taxes & fees
24 Nov - 25 Nov
The Niantic Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
7.2 out of 10, Good, (459)
"🙂"
United States
Jared
The price is AED 263
AED 302 total
includes taxes & fees
30 Nov - 1 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Front of property
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (207)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is AED 619
AED 854 total
includes taxes & fees
23 Nov - 24 Nov
The Sagaponack
Exterior
House on Chase Creek

House on Chase Creek

2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is AED 679
AED 776 total
includes taxes & fees
24 Nov - 25 Nov
House on Chase Creek
Terrace/patio
Shorewood Inn

Shorewood Inn

2.5 star property
Riverhead
8.4 out of 10, Very Good, (706)
"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "
United States
Shelly
Shorewood Inn
Exterior
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (67)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Exterior
Liberty Inn

Liberty Inn

2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is AED 262
AED 301 total
includes taxes & fees
21 Dec - 22 Dec
Liberty Inn
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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southold Hotel Reviews

The Sagaponack

The Sagaponack

10/10 Excellent
"Beautiful room, loved the treats at the galley."
Andrew 1-night trip
Posted 2 days ago
The Sagaponack

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.