Search Vacation Homes 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
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (3)
"good experience"
The price is HK$4,670
HK$9,025 total
includes taxes & fees
13 Oct - 14 Oct
Beautifully farmhouse
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

9.6 out of 10, Exceptional, (51)
"Great stay, charming cottage, hope to return"
The price is HK$841
HK$2,063 total
includes taxes & fees
13 Oct - 14 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Rogers Lake House (87) · CT College+Beach+USCGA
Property grounds

Rogers Lake House (87) · CT College+Beach+USCGA

10.0 out of 10, Exceptional, (2)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
The price is HK$672
HK$3,118 total
includes taxes & fees
14 Oct - 15 Oct
Rogers Lake House (87) · CT College+Beach+USCGA
Spacious 5-bedroom house with water views and 2 houses from the bay.
Beach

Spacious 5-bedroom house with water views and 2 houses from the bay.

The price is HK$31,131
HK$50,426 total
includes taxes & fees
16 Oct - 17 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.
Cozy quiet gem, private & fenced in backyard
Fridge, microwave, oven, stovetop

Cozy quiet gem, private & fenced in backyard

9.4 out of 10, Exceptional, (3)
"good times"
The price is HK$771
HK$7,060 total
includes taxes & fees
16 Oct - 17 Oct
Cozy quiet gem, private & fenced in backyard
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is HK$1,366
HK$3,161 total
includes taxes & fees
13 Oct - 14 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Private completely fenced in property. Near beach
Terrace/patio

Private completely fenced in property. Near beach

9.6 out of 10, Exceptional, (22)
"The place is in nice neighborhood and private entrance. It has all the amenities for a good staying. Definitely will stay again in the future."
The price is HK$1,206
HK$10,466 total
includes taxes & fees
26 Oct - 27 Oct
Private completely fenced in property. Near beach
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Outdoor pool, a heated pool

BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
The price is HK$23,348
HK$45,695 total
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
American Beech in Greenport - Petite King Room 7
Terrace/patio

American Beech in Greenport - Petite King Room 7

9.0 out of 10, Wonderful, (4)
"Great job "
The price is HK$1,549
HK$2,383 total
includes taxes & fees
13 Oct - 14 Oct
American Beech in Greenport - Petite King Room 7
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Private kitchen

Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool

10.0 out of 10, Exceptional, (1)
"We were escaping NYC for the weekend and exploring real estate in the area. This house was absolutely beautiful and way bigger than we needed. Unfortunately it was rainy out and we really didn’t get to spend too much time in the house since we were driving around it looks like it has a beautiful property with a pool etc. so hopefully we can come back in the summer."
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Oven, stovetop, dishwasher

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is HK$3,884
HK$7,016 total
includes taxes & fees
13 Oct - 14 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Terrace/patio

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

9.6 out of 10, Exceptional, (133)
"Great older house with everything you need to have a great time. Family event with 6 adults and 2 dogs enjoyed the house, the yard, and the area. Strongly recommend."
The price is HK$2,335
HK$4,526 total
includes taxes & fees
13 Oct - 14 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Private beach on a fenced in property sunset views
Terrace/patio

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
The price is HK$2,763
HK$11,986 total
includes taxes & fees
20 Oct - 21 Oct
Private beach on a fenced in property sunset views
Historic New England home ,Reunions Beach pass
Fridge, microwave, oven, stovetop

Historic New England home ,Reunions Beach pass

9.2 out of 10, Wonderful, (90)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
The price is HK$2,335
HK$4,409 total
includes taxes & fees
13 Oct - 14 Oct
Historic New England home ,Reunions Beach pass
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Outdoor pool, a heated pool

6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches

10.0 out of 10, Exceptional, (44)
"Catherine was a great homeowner and made sure everything was organized prior to our arrival. She was very kind and easy to communicate with. She also was able to make sure we could have an early check in. "
The price is HK$15,641
HK$27,269 total
includes taxes & fees
20 Oct - 21 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
Beachside Bliss w/ Game Room, Gym & Golf Green
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property
The price is HK$3,308
HK$4,279 total
includes taxes & fees
25 Oct - 26 Oct
Beachside Bliss w/ Game Room, Gym & Golf Green
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is HK$35,023
HK$49,216 total
includes taxes & fees
14 Oct - 15 Oct
Sag Harbor Water View w Dock 1.5ml from town
Charming Northfork Townhouse- walk to all
Fridge, microwave, oven, stovetop

Charming Northfork Townhouse- walk to all

10.0 out of 10, Exceptional, (5)
"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"
The price is HK$2,957
HK$5,691 total
includes taxes & fees
15 Oct - 16 Oct
Charming Northfork Townhouse- walk to all
Village gem walk to Main Street fenced in property
Smart TV, fireplace

Village gem walk to Main Street fenced in property

9.2 out of 10, Wonderful, (5)
"Second year at this lovely house for the 4th of July extended weekend. The hosts are responsive and helpful, and the house is exactly what you need for 2-3 people. Very clean, nicely decorated, kitchen was nicely stocked. It is in a great location. Easily able to walk into town for shopping or dining."
The price is HK$3,191
HK$8,181 total
includes taxes & fees
13 Oct - 14 Oct
Village gem walk to Main Street fenced in property
Work and Play Special! Extended Stay Discount
Property grounds

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
The price is HK$6,226
HK$11,177 total
includes taxes & fees
6 Nov - 7 Nov
Work and Play Special! Extended Stay Discount
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
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

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Very nice resort hotel in excellent condition. Everything looks new and well maintained. Dinners in main dining room were all excellent. "
Mark 1-night trip
Posted 1 day ago
Water's Edge Resort & Spa

Find out more about Southold

Southold Vacation Homes information

Number of reviews
336
Accommodation
1800 Vacation Homes
Lowest Price
HK$2,063
Highest Price
HK$50,426

Explore a world of travel with Expedia