Holiday Homes in Southold

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Featured Holiday Homes in Southold

Beautifully farmhouse
Terrace/patio

Beautifully farmhouse

10.0 out of 10, Exceptional, (2)
"good experience"
The price is AU$1,769
includes taxes & fees
9 Sept - 10 Sept
Beautifully farmhouse
Stunning Southampton Village Modern Home
Living area

Stunning Southampton Village Modern Home

The price is AU$26,729
includes taxes & fees
9 Sept - 10 Sept
Stunning Southampton Village Modern Home
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 AU$10,788
includes taxes & fees
17 Sept - 18 Sept
Sag Harbor Water View w Dock 1.5ml from town
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 AU$713
includes taxes & fees
9 Sept - 10 Sept
Rogers Lake House (87) · CT College+Beach+USCGA
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, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is AU$628
includes taxes & fees
7 Sept - 8 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Fridge, microwave, oven, stovetop

The Bay Cottage · Rocky Neck Park, Beach & Niantic

2.0 star property
9.0 out of 10, Wonderful, (4)
"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)."
The price is AU$584
includes taxes & fees
7 Sept - 8 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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 AU$10,081
includes taxes & fees
13 Sept - 14 Sept
Spacious 5-bedroom house with water views and 2 houses from the bay.
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 AU$402
includes taxes & fees
7 Sept - 8 Sept
Shoreline Oasis
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, (42)
"the property was lovely and well equipped with all amenties. Comfortable and located in an area which is accessible for all towns in the Hamptons"
The price is AU$5,350
includes taxes & fees
2 Oct - 3 Oct
6 Bedroom Bridgehampton Estate, Private Tennis, Minutes from Ocean Beaches
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
9.2 out of 10, Wonderful, (5)
"A fantastic location, and would certainly stay again! The bed was a bit hard but we all like something different. "
The price is AU$1,411
includes taxes & fees
5 Sept - 6 Sept
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
Work and Play Special! Extended Stay Discount
Property grounds

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (50)
"we were pleased to find a beautiful, quiet place to stay and so close to the Vine Street Cafe we could walk"
The price is AU$2,057
includes taxes & fees
14 Sept - 15 Sept
Work and Play Special! Extended Stay Discount
September is the New August!
Outdoor pool, a heated pool

September is the New August!

10.0 out of 10, Exceptional, (88)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
September is the New August!
East End Escape
Outdoor dining

East End Escape

The price is AU$849
includes taxes & fees
5 Sept - 6 Sept
East End Escape
Historic New England home ,Reunions Beach pass
Fridge, microwave, oven, stovetop

Historic New England home ,Reunions Beach pass

9.2 out of 10, Wonderful, (88)
"House was perfect for family get together. Enjoyed walking into town for afternoon shopping and dining."
The price is AU$992
includes taxes & fees
7 Sept - 8 Sept
Historic New England home ,Reunions Beach pass
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 AU$574
includes taxes & fees
2 Oct - 3 Oct
American Beech in Greenport - Petite King Room 7
Bay Access Cottage + Pilates Gym
Beach nearby, sun-loungers, beach towels

Bay Access Cottage + Pilates Gym

2.0 star property
The price is AU$1,000
includes taxes & fees
9 Sept - 10 Sept
Bay Access Cottage + Pilates Gym
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, (1)
"Communication with the property manager was an A. Highly recommend this home! "
The price is AU$3,711
includes taxes & fees
14 Sept - 15 Sept
5 Bedrooms! 4 Min to the Beach! HEATED POOL!
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (185)
"House was more then I can imagine , host was great , house literally have anything you forgot at home . "
The price is AU$1,380
includes taxes & fees
2 Oct - 3 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
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 AU$1,168
includes taxes & fees
8 Sept - 9 Sept
Charming 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

Find out more about Southold

Find out more about Southold

Southold Holiday Homes information

Number of reviews
Accommodation
1926 Holiday Homes
Lowest Price
AU$628
Highest Price
AU$1,411

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