Holiday Homes in Southold

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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Featured Holiday Homes in Southold

Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (3)
"good experience"
The price is NZ$2,025
includes taxes & fees
27 Oct - 28 Oct
Beautifully farmhouse
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 NZ$11,021
includes taxes & fees
13 Oct - 14 Oct
Sag Harbor Water View w Dock 1.5ml from town
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 NZ$457
includes taxes & fees
13 Oct - 14 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
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 NZ$702
includes taxes & fees
13 Oct - 14 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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 NZ$11,147
includes taxes & fees
14 Oct - 15 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.
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 NZ$729
includes taxes & fees
4 Nov - 5 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
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 NZ$10,144
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Shoreline Oasis
Exterior

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is NZ$454
includes taxes & fees
13 Oct - 14 Oct
Shoreline Oasis
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 NZ$1,577
includes taxes & fees
10 Oct - 11 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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 NZ$6,053
includes taxes & fees
20 Oct - 21 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
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 NZ$529
includes taxes & fees
13 Oct - 14 Oct
American Beech in Greenport - Petite King Room 7
Cozy 5 Bedroom With Wi-fi And Air Condition
Private kitchen

Cozy 5 Bedroom With Wi-fi And Air Condition

The price is NZ$2,978
includes taxes & fees
10 Oct - 11 Oct
Cozy 5 Bedroom With Wi-fi And Air Condition
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 NZ$1,005
includes taxes & fees
13 Oct - 14 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Work and Play Special! Extended Stay Discount
Property grounds

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (52)
"Beautiful pool, badminton net, lots of outdoor seating areas. Location is easy, very close to ferry and nature preserve."
The price is NZ$2,476
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
East End Escape
Outdoor dining

East End Escape

The price is NZ$947
includes taxes & fees
10 Oct - 11 Oct
East End Escape
Minutes from the beach, brand new 4 bedroom
Fridge, microwave, oven, stovetop

Minutes from the beach, brand new 4 bedroom

10.0 out of 10, Exceptional, (2)
"Great convenient location. Perfect house for a group with plenty of bathrooms and king size beds. "
The price is NZ$1,912
includes taxes & fees
12 Oct - 13 Oct
Minutes from the beach, brand new 4 bedroom
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 NZ$977
includes taxes & fees
10 Oct - 11 Oct
Historic New England home ,Reunions Beach pass
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."
The price is NZ$1,170
includes taxes & fees
13 Oct - 14 Oct
Modern 3BR 2BA Home w/ Patio & Outdoor Salt Pool
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 NZ$1,321
includes taxes & fees
13 Oct - 14 Oct
Charming Northfork Townhouse- walk to all
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
Smart TV, fireplace, computer monitors, printers

5 Bedrooms! 4 Min to the Beach! HEATED POOL!

10.0 out of 10, Exceptional, (2)
"awesome house and awesome host"
The price is NZ$5,040
includes taxes & fees
10 Oct - 11 Oct
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
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.
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Top Southold Hotel Reviews

Greenview Inn Riverhead

Greenview Inn Riverhead

10/10 Excellent
"I was really impressed with the modern, clean room. I loved the sliding barn door..clean, white bedding & refillable soap & shampoo & conditioner. No more little plastic bottles that never hold enough to even wash one person’s hair. I also lined the separate reading lights. The gentleman checking us in was pleasant and it took a very short time. I would definitely consider another visit next time I am visiting the North Fork of Long Island."
carol 1-night trip
Posted 3 days ago
Greenview Inn Riverhead

Find out more about Southold

Find out more about Southold

Southold Holiday Homes information

Number of reviews
304
Accommodation
1800 Holiday Homes
Lowest Price
NZ$454
Highest Price
NZ$11,147

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