Photo by Benny Goh
Search Vacation 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
Holiday Home in Calverton
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC8.6 out of 10, Excellent, (8 reviews)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
Nicole A.
The price is HK$3,516
HK$6,557 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Home in Greenport
American Beech in Greenport - Petite King Room 79.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
Parent From The Heart, Inc. E.
The price is HK$1,323
HK$2,030 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Home in Old Lyme
Insta-worthy Couples Retreat: Perfect for romantic getaway!9.4 out of 10, Exceptional, (53 reviews)
"Pet friendly, good communication with host, great location and friendly neighborhood. Comfortable cottage. "
Ed F.
The price is HK$939
HK$2,206 total
includes taxes & fees
13 Apr - 14 Apr
Holiday Home in Old Lyme
Rogers Lake House (87) · CT College+Beach+USCGA10.0 out of 10, Exceptional, (5 reviews)
"Communication was excellent. "
Katy C.
The price is HK$1,231
HK$3,850 total
includes taxes & fees
30 Mar - 31 Mar
Holiday Home in Clinton
Stylish Modern Stay Steps from the Ocean10.0 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 HK$1,409
HK$2,795 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Home in Greenport
Renovated Townhouse walk to all9.6 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 HK$2,078
HK$4,459 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Home in Greenport
Northfork Townhouse walk to all10.0 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 HK$2,043
HK$4,409 total
includes taxes & fees
16 Mar - 17 Mar
Holiday Home in Hampton Bays
Immaculate Waterfront 2 bedroom!10.0 out of 10, Exceptional, (5 reviews)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
Michael L.
The price is HK$2,544
HK$4,937 total
includes taxes & fees
16 Mar - 17 Mar
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
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Southold Hotel Reviews
The Harbor Front Inn
8/10 Good
Find out more about Southold
Southold Vacation Homes information
Number of reviews | 98 |
|---|---|
Accommodation | 1733 Vacation Homes |
Lowest Price | HK$2,030 |
Highest Price | HK$8,840 |
Explore a world of travel with Expedia
- Vacation Homes in Southampton
- Resorts in Wainscott
- Apartments in Shelter Island Heights
- Villas in East Hampton
- Bridgehampton Hotels
- Villas in Village of Southampton
- 4 Star Hotels in Sag Harbor
- B&B in Southampton
- Hotels near Pindar Vineyards
- Hampton Bays Hotels
- Cheap Hotels in Sag Harbor
- Hotel with Pool Hotels in Sag Harbor
- Noyack Hotels
- Cabin Rentals in Southampton
- Hotels near Agawam Park
- Hotels near SagPond Vineyards
- Hotels near Shinnecock Hills Golf Course
- 5 Star Hotels in Greenport
- Apartments in Sag Harbor
- Aparthotels in Hamptons
- B&B in Greenport
- 4 Star Hotels in Shelter Island Heights
- Wedding Hotels in Shelter Island Heights
- Sag Harbor Hotels
- Cheap Hotels in Hamptons
- Cabin Rentals in Shelter Island Heights
- Beach Hotel Hotels in Sag Harbor
- Family Hotel Hotels in Sag Harbor
- 4 Star Hotels in Hamptons
- Southampton Hotels
- Villas in Southampton
- Villas in Hamptons
- Jamesport Hotels
- B&B in Shelter Island Heights
- Orient Hotels
- Cottages in Sag Harbor
- Cottages in Hamptons
- Family Hotel Hotels in East Marion
- Pet-Friendly Hotel Hotels in Southampton
- 5 Star Hotels in Sag Harbor
- Cottages in East Hampton
- Residences in Hamptons
- Hotels near Orient Beach State Park
- Hotels near Macari Vineyards
- Apartments in Hamptons
- Winery Hotel Hotels in Shelter Island Heights
- Hotels near Shelter Island Country Club
- Condo Rentals in Hamptons
- Hotels near Sunset Beach
- Boutique Hotel Hotels in Jamesport
- Beach Hotel Hotels in Peconic
- Historic Hotel Hotels in Greenport
- Wyndham Hotels in Shelter Island Heights
- Hotels near Raphael Winery
- B&B in Jamesport
- Hotel with Pool Hotels in Southampton
- 3 Star Hotels in Southampton
- Inns in Hamptons
- Resorts in Hamptons
- Hotels near Harbes Family Farm
- Peconic Hotels
- Beach Hotel Hotels in Hamptons
- Hotels near Mattebella Vineyards
- Luxury Hotel Hotels in Sag Harbor
- Pet-Friendly Hotel Hotels in East Marion
- Shelter Island Hotels
- Motels in Mattituck
- Hotels near Hallockville Museum Farm
- Bar Hotel Hotels in Hamptons
- Vacation Homes in Hamptons
- Family Hotel Hotels in East Hampton
- B&B in Hamptons
- Winery Hotel Hotels in Bridgehampton
- Cabin Rentals in Hamptons
- Hotels near Duck Walk Vineyards
- B&B in Laurel
- Vacation Homes in East Hampton
- Cheap Hotels in Southampton
- Cottages in Southampton
- 5 Star Hotels in Hamptons
- Southampton Historical Museum
- Southampton Holidays
- Sag Harbor Old Burying Ground
- Shelter Island Heights Holidays
- North Main Street Historic District
- Mashashimuet Park
- Martha Clara Vineyards
- Visit North Fork
- Visit Hay Beach
- Visit Southampton
- Southampton Cultural Center
- Noyac Golf Club
- Visit Shelter Island