Photo by Benny Goh
Holiday Homes in Southold
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Southold holiday homes
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Insta-worthy Couples Retreat: Perfect for romantic getaway!Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
Janet B.
The price is €233
includes taxes & fees
29 Apr - 30 Apr
The price is €370
includes taxes & fees
21 Apr - 22 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic
The Bay Cottage · Rocky Neck Park, Beach & NianticEast Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
Sarah G.
The price is €353
includes taxes & fees
21 Apr - 22 Apr
American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
Parent From The Heart, Inc. E.
The price is €227
includes taxes & fees
29 Apr - 30 Apr
Rogers Lake House (87) · CT College+Beach+USCGA
Rogers Lake House (87) · CT College+Beach+USCGAOld Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
john18250
The price is €450
includes taxes & fees
5 May - 6 May
Renovated Townhouse walk to all
Renovated Townhouse walk to allGreenport
9.6 out of 10, Exceptional, (10 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
Laura B.
The price is €535
includes taxes & fees
22 Apr - 23 Apr
Northfork Townhouse walk to all
Northfork Townhouse walk to allGreenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
Beth R.
The price is €506
includes taxes & fees
22 Apr - 23 Apr
Stylish Modern Stay Steps from the Ocean
Stylish Modern Stay Steps from the OceanClinton
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
Kelly Z.
The price is €231
includes taxes & fees
2 May - 3 May
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.
Find holiday rentals that suit your style
Private holiday homes
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Southold Hotel Reviews
The Bentley Hotel Southampton
10/10 Excellent
Find out more about Southold
Southold Holiday Homes information
Number of reviews | 325 |
|---|---|
Accommodation | 1664 Holiday Homes |
Lowest Price | €227 |
Highest Price | €2,435 |