HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
HomeAway uses cookies to improve your site experience. Learn more. By continuing, you consent to our use of cookies.
Verified Review icon check navigate-up navigate-left navigate-right expand mail svg-lightning svg-24hr svg-house svg-sleeps svg-bedrooms svg-bathrooms svg-stay svg-toilet calendar svg-report-flag pet-dog svg-multiunit Default Owner Icon heart-filled Family icon

Make a Holiday Rental House in Southold, Long Island Your Home Away From Home

At the north-eastern tip of Long Island in the state of New York lies the peaceful town of Southold. The town has been a settlement since the 17th century and is steeped in American history. A Southold holiday rental house will offer spectacular sea views as well as the opportunity to experience a range of activities.

Things to Do on Holiday to Southold, Long Island

One of the main attractions of a Southold holiday is the beaches. The town has several unspoilt, sandy beaches that are perfect for sunbathing and swimming. Visitors can also enjoy a range of watersports such as sailing, windsurfing, fishing, jet skiing and water skiing. Other activities available in the town include bird watching, horse riding, cycling, golf and nature walks.

Also worth a visit on a Southold holiday is the Southold Indian Museum. This building has a collection of artefacts pertaining to the tribes that inhabited the area for thousands of years. Visitors can view pottery relics, spear heads, Indian art, children’s toys and examples of the fishing methods used by these Indians.

Places to Visit on Holiday to Southold, Long Island

Approximately half an hour’s drive south-west of Southold is the town of Riverhead. Not only does the town offer paddle-boat cruises, beaches and parks, it is home to the Riverhead Raceway. This is a quarter-mile oval track which is now the only racing circuit on the whole of Long Island. Visitors can enjoy NASCAR, Enduro, demolition derby’s and monster trucks throughout the year at the venue.

Also worth a visit in the town is the Hallockville Museum. The museum is a farm homestead that dates back to the 18th century. As well as the actual homestead itself there are a range of original outbuildings, a barn, old machinery and beautiful gardens.

Weather in Southold, Long Island

Long Island is blessed with warm, somewhat humid summers and cold winters. The warmest months of the year to go on a Southold holiday are June, July and August, when the temperature can reach as high as 28°C during the day. December and January are generally the coldest months with average daytime temperatures of 3°C. Snow can fall to an amount of 20 inches during the winter. Visitors should be aware that Southold and the rest of Long Island is susceptible to thunderstorms and mild hurricanes.

Travel to Southold, Long Island Visitors on a Southold holiday will arrive at the Long Island MacArthur Airport (ISP) which is approximately 74 kilometres from the town. Operators that offer cheap, regular flights to the area include BMI, US Airways, British Airways, United Airlines and Continental Airlines. Travellers can depart from several UK airports such as London Heathrow (LHR), Gatwick (LGW), Aberdeen (ABZ), Manchester (MAN) and Birmingham (BHX).

Cancel Clear Filters Apply Filters
More Filters

Price Per Night

£ £

Bedrooms

Bathrooms

Payment Options

Property Type

Popular Searches

Facilities

Location Type

Local Area

Properties good for

Property Details

Clear Filters
Use filters to narrow your search results!
Viewed 19 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
avg/night
Viewed 26 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 2500 sq. ft.
Exceptional! 5/5
(8 reviews)
avg/night
8
Viewed 51 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • Separate Toilets
Exceptional! 5/5
(16 reviews)
avg/night
16
Viewed 30 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
avg/night
1
Viewed 19 times in the last 48 hours
  • 4 BR House
  • 4 BA
  • 2300 sq. ft.
avg/night
Viewed 23 times in the last 48 hours
Premier Partner
  • 3 BR House
  • 2 BA
Exceptional! 5/5
(56 reviews)
avg/night
56
Viewed 37 times in the last 48 hours
  • 3 BR House
  • 2 BA
Wonderful! 4.9/5
(10 reviews)
avg/night
10
Viewed 14 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 2100 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
6
Viewed 56 times in the last 48 hours
  • 3 BR House
  • 3 BA
  • 2001 sq. ft.
avg/night
Viewed 53 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • 1400 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
5
  • 3 BR Cottage
  • 1 BA
Exceptional! 5/5
(11 reviews)
avg/night
11
Viewed 25 times in the last 48 hours
  • 2 BR Cottage
  • 1 BA
  • 900 sq. ft.
avg/night
2
Viewed 8 times in the last 48 hours
  • 5 BR House
  • 1 BA
  • Separate Toilet
  • 2200 sq. ft.
avg/night
1
Viewed 36 times in the last 48 hours
  • 4 BR House
  • 3 BA
  • 3000 sq. ft.
Exceptional! 5/5
(40 reviews)
avg/night
40
  • 4 BR House
  • 3 BA
  • Separate Toilet
  • 2800 sq. ft.
avg/night
Viewed 9 times in the last 48 hours
  • 5 BR House
  • 3 BA
  • Separate Toilet
  • 3400 sq. ft.
Exceptional! 5/5
(6 reviews)
avg/night
6
Viewed 7 times in the last 48 hours
  • 3 BR House
  • 2 BA
avg/night
4
Viewed 13 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
Wonderful! 4.8/5
(6 reviews)
avg/night
6
Viewed 24 times in the last 48 hours
  • 4 BR House
  • 4 BA
avg/night
Viewed 19 times in the last 48 hours
  • 3 BR House
  • 2 BA
avg/night
Viewed 15 times in the last 48 hours
  • 5 BR Bungalow
  • 2 BA
  • 1160 sq. ft.
avg/night
Viewed 13 times in the last 48 hours
  • 5 BR House
  • 4 BA
  • 5000 sq. ft.
avg/night
  • 3 BR House
  • 2 BA
  • 1200 sq. ft.
avg/night
1
Viewed 6 times in the last 48 hours
  • 3 BR Farmhouse
  • 2 BA
  • Separate Toilet
Exceptional! 5/5
(9 reviews)
avg/night
9
  • 3 BR House
  • 3 BA
avg/night
1
  • 3 BR House
  • 3 BA
Wonderful! 4.8/5
(12 reviews)
avg/night
12
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 1600 sq. ft.
View details for price
1
Viewed 12 times in the last 48 hours
  • 3 BR Cottage
  • 2 BA
  • Separate Toilet
  • 1450 sq. ft.
avg/night
3
Viewed 23 times in the last 48 hours
  • 2 BR House
  • 1 BA
  • 650 sq. ft.
avg/night
1
Viewed 5 times in the last 48 hours
  • 4 BR House
  • 2 BA
  • 1540 sq. ft.
avg/night
2
  • 4 BR House
  • 3 BA
  • 2500 sq. ft.
avg/night
2
  • 5 BR House
  • 3 BA
  • Separate Toilet
  • 3200 sq. ft.
avg/night
1
Viewed 14 times in the last 48 hours
  • 3 BR Farmhouse
  • 2 BA
avg/night
  • 5 BR House
  • 3 BA
avg/night
  • 4 BR House
  • 3 BA
avg/night
  • 3 BR House
  • 2 BA
avg/night
Viewed 9 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • Separate Toilet
  • 2000 sq. ft.
avg/night
Viewed 9 times in the last 48 hours
  • 5 BR House
  • 3 BA
  • Separate Toilet
  • 5000 sq. ft.
Exceptional! 5/5
(5 reviews)
avg/night
5
Viewed 42 times in the last 48 hours
  • 5 BR House
  • 4 BA
avg/night
Viewed 19 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
  • 2700 sq. ft.
avg/night
  • 3 BR House
  • 1 BA
  • Separate Toilet
avg/night
  • 3 BR House
  • 3 BA
avg/night
1
  • 4 BR Farmhouse
  • 2 BA
  • Separate Toilet
  • 2600 sq. ft.
avg/night
Viewed 120 times in the last 48 hours
  • 6 BR House
  • 4 BA
  • 4000 sq. ft.
avg/night
3
Viewed 7 times in the last 48 hours
  • 3 BR House
  • 1 BA
  • Separate Toilet
  • 1300 sq. ft.
Very Good! 4.2/5
(5 reviews)
avg/night
5
Viewed 9 times in the last 48 hours
  • 2 BR House
  • 3 BA
  • 1250 sq. ft.
avg/night
  • 3 BR House
  • 2 BA
  • 1700 sq. ft.
Exceptional! 5/5
(7 reviews)
avg/night
7
  • 4 BR House
  • 1 BA
  • Separate Toilet
  • 2000 sq. ft.
avg/night
Viewed 6 times in the last 48 hours
  • 3 BR House
  • 2 BA
  • Separate Toilet
avg/night
  • 4 BR House
  • 2 BA
  • Separate Toilets
  • 3000 sq. ft.
avg/night
3

Southold Holiday Homes & Cottages (300+)