Holiday Homes in Southold

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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Featured Holiday Homes in Southold

Terrace/patio
Beautifully farmhouse
Beautifully farmhouse
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is AU$1,804
includes taxes & fees
27 Oct - 28 Oct
Beautifully farmhouse
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA
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!"
United States
Hemie J.
The price is AU$624
includes taxes & fees
11 Nov - 12 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Insta-worthy Couples Retreat: Perfect for romantic getaway!
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is AU$364
includes taxes & fees
29 Oct - 30 Oct
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Fridge, microwave, oven, stovetop
Cozy quiet gem, private & fenced in backyard
Cozy quiet gem, private & fenced in backyard
9.4 out of 10, Exceptional, (3)
"Perfect stay outside of the hustle and bustle of Manhattan. The house offered just what we needed a refugee from the city. With plenty of comfortable rooms for the six of us."
United States
Shakirah S.
The price is AU$1,473
includes taxes & fees
24 Oct - 25 Oct
Cozy quiet gem, private & fenced in backyard
Terrace/patio
Year-Round Private Jacuzzi / Peaceful Fenced Yard
Year-Round Private Jacuzzi / Peaceful Fenced Yard
9.6 out of 10, Exceptional, (22)
"The house was very spacious and beautiful! The pool and patio were the major highlights. Pool was crystal clear and clean. We enjoyed our stay so much and hope to be back. Owner was very responsive with our questions "
United States
Jackie S.
The price is AU$1,980
includes taxes & fees
26 Oct - 27 Oct
Year-Round Private Jacuzzi / Peaceful Fenced Yard
Outdoor pool, a heated pool
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
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!!"
United States
Stephanie M.
The price is AU$8,535
includes taxes & fees
3 Nov - 4 Nov
BRAND NEW 7BR7BA Southampton Estate - Heated Salt Pool, Mins to Beach & Town
Outdoor pool, a heated pool
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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! "
United States
James S.
The price is AU$582
includes taxes & fees
29 Oct - 30 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green
Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
The price is AU$741
includes taxes & fees
4 Nov - 5 Nov
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio
American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7
9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is AU$460
includes taxes & fees
26 Oct - 27 Oct
American Beech in Greenport - Petite King Room 7
Terrace/patio
Private beach on a fenced in property sunset views
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."
United States
Hanna M.
The price is AU$2,285
includes taxes & fees
26 Oct - 27 Oct
Private beach on a fenced in property sunset views
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.
Spacious 5-bedroom house with water views and 2 houses from the bay.
The price is AU$10,014
includes taxes & fees
27 Oct - 28 Oct
Spacious 5-bedroom house with water views and 2 houses from the bay.
Terrace/patio
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
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."
United States
Ray S.
The price is AU$906
includes taxes & fees
27 Oct - 28 Oct
Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
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. "
United States
Riyao
The price is AU$1,422
includes taxes & fees
24 Oct - 25 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Terrace/patio
Immaculate Waterfront 2 bedroom!
Immaculate Waterfront 2 bedroom!
10.0 out of 10, Exceptional, (5)
"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."
United States
Michael L.
The price is AU$1,005
includes taxes & fees
26 Oct - 27 Oct
Immaculate Waterfront 2 bedroom!
Property grounds
Work and Play Special! Extended Stay Discount
Work and Play Special! Extended Stay Discount
10.0 out of 10, Exceptional, (52)
"Really great property, had a relaxing lovely time!"
United States
Nava S.
The price is AU$2,073
includes taxes & fees
5 Nov - 6 Nov
Work and Play Special! Extended Stay Discount
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated
Northfork Townhouse- walk to all/ newly renovated
9.6 out of 10, Exceptional, (9)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is AU$1,239
includes taxes & fees
9 Nov - 10 Nov
Northfork Townhouse- walk to all/ newly renovated
Fridge, microwave, oven, stovetop
Historic New England home ,Reunions Beach pass
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."
United States
Jennifer D.
The price is AU$895
includes taxes & fees
7 Nov - 8 Nov
Historic New England home ,Reunions Beach pass
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town
Sag Harbor Water View w Dock 1.5ml from town
The price is AU$9,922
includes taxes & fees
25 Oct - 26 Oct
Sag Harbor Water View w Dock 1.5ml from town
Fridge, microwave, oven, stovetop
Minutes from the beach, brand new 4 bedroom
Minutes from the beach, brand new 4 bedroom
10.0 out of 10, Exceptional, (3)
"perfect for families"
United States
Okito H.
The price is AU$1,728
includes taxes & fees
24 Oct - 25 Oct
Minutes from the beach, brand new 4 bedroom
Fridge, microwave, oven, stovetop
Northfork Townhouse walk to all
Northfork Townhouse walk to all
2.0 star property
The price is AU$1,077
includes taxes & fees
26 Oct - 27 Oct
Northfork Townhouse walk to all
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

Spark by Hilton Guilford

Spark by Hilton Guilford

10/10 Excellent
"One night. Friendly staff. All good."
Thomas 1-night trip
Posted 1 day ago
Spark by Hilton Guilford

Find out more about Southold

Southold Holiday Homes information

Number of reviews
312
Accommodation
1800 Holiday Homes
Lowest Price
AU$364
Highest Price
AU$10,014