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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).

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Viewed 26 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 2500 sq. ft.
Exceptional! 5/5
(8 reviews)
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House #340957
8
  • 3 BR
  • 2 BA
  • Separate Toilet
avg/night
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Viewed 76 times in the last 48 hours
  • 3 BR
  • 1 BA
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Exceptional! 5/5
(16 reviews)
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16
Viewed 51 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1500 sq. ft.
Wonderful! 4.9/5
(36 reviews)
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Cottage #285350vb
36
Viewed 72 times in the last 48 hours
  • 3 BR
  • 2 BA
Wonderful! 4.9/5
(9 reviews)
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9
Viewed 40 times in the last 48 hours
Premier Partner
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  • 2 BA
Exceptional! 5/5
(55 reviews)
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55
Viewed 42 times in the last 48 hours
  • 4 BR
  • 4 BA
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Viewed 32 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 2100 sq. ft.
Exceptional! 5/5
(6 reviews)
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6
Viewed 78 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 3000 sq. ft.
Exceptional! 5/5
(39 reviews)
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39
Viewed 54 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 1450 sq. ft.
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Cottage #896250vb
3
Viewed 44 times in the last 48 hours
  • 6 BR
  • 4 BA
  • 4000 sq. ft.
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3
Viewed 53 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
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1
Viewed 25 times in the last 48 hours
  • 3 BR
  • 3 BA
  • 2000 sq. ft.
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House #4769398
Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
Exceptional! 5/5
(9 reviews)
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9
  • 3 BR
  • 3 BA
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1
Viewed 9 times in the last 48 hours
  • 5 BR
  • 1 BA
  • Separate Toilet
  • 2200 sq. ft.
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House #4640263
1
Viewed 42 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 1600 sq. ft.
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Farmhouse #875221vb
4
Viewed 18 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 3200 sq. ft.
Wonderful! 4.9/5
(11 reviews)
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11
  • 3 BR
  • 3 BA
Wonderful! 4.8/5
(12 reviews)
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House #356226vb
12
Viewed 15 times in the last 48 hours
  • 4 BR
  • 3 BA
  • Separate Toilet
  • 3000 sq. ft.
Exceptional! 5/5
(7 reviews)
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House #4113898
7
  • 2 BR
  • 1 BA
  • 700 sq. ft.
Exceptional! 5/5
(8 reviews)
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Cottage #297578
8
Viewed 50 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 900 sq. ft.
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2
Viewed 10 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 1600 sq. ft.
View details for price
House #4638258
1
Viewed 27 times in the last 48 hours
  • 4 BR
  • 3 BA
  • 2800 sq. ft.
Wonderful! 4.9/5
(9 reviews)
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House #821199vb
9
Viewed 35 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1400 sq. ft.
Exceptional! 5/5
(5 reviews)
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House #587577vb
5
Viewed 19 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1200 sq. ft.
Exceptional! 5/5
(7 reviews)
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Cottage #587073vb
7
Viewed 35 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1000 sq. ft.
Exceptional! 5/5
(38 reviews)
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Cottage #966043
38
Viewed 17 times in the last 48 hours
  • 5 BR
  • 3 BA
  • Separate Toilet
  • 3400 sq. ft.
Exceptional! 5/5
(6 reviews)
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6
Viewed 10 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
Wonderful! 4.8/5
(6 reviews)
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6
Viewed 21 times in the last 48 hours
  • 3 BR
  • 2 BA
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Viewed 13 times in the last 48 hours
Premier Partner
  • 5 BR
  • 2 BA
Exceptional! 5/5
(13 reviews)
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13
  • 2 BR
  • 1 BA
Excellent! 4.3/5
(10 reviews)
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10
Viewed 36 times in the last 48 hours
  • 4 BR
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  • 2400 sq. ft.
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3
Viewed 12 times in the last 48 hours
  • 5 BR
  • 2 BA
  • 1160 sq. ft.
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Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
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Viewed 5 times in the last 48 hours
  • 2 BR
  • 1 BA
Exceptional! 5/5
(8 reviews)
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House #3561038
8
  • 4 BR
  • 1 BA
  • Separate Toilet
  • 2000 sq. ft.
avg/night
House #1032216vb
Viewed 11 times in the last 48 hours
  • 3 BR
  • 1 BA
  • Separate Toilet
  • 1300 sq. ft.
Very Good! 4.2/5
(5 reviews)
avg/night
House #605419vb
5
  • 4 BR
  • 2 BA
  • Separate Toilets
  • 3000 sq. ft.
avg/night
House #493365vb
3
Viewed 9 times in the last 48 hours
  • 5 BR
  • 3 BA
  • Separate Toilet
  • 5000 sq. ft.
Exceptional! 5/5
(5 reviews)
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House #4360232
5
Viewed 6 times in the last 48 hours
  • 3 BR
  • 2 BA
  • Separate Toilet
  • 2700 sq. ft.
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Viewed 10 times in the last 48 hours
  • 3 BR
  • 1 BA
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  • 2000 sq. ft.
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  • 3 BR
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Viewed 25 times in the last 48 hours
  • 2 BR
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  • 1250 sq. ft.
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Viewed 13 times in the last 48 hours
  • 3 BR
  • 2 BA
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  • 5 BR
  • 3 BA
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1
Viewed 15 times in the last 48 hours
  • 4 BR
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  • 2500 sq. ft.
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Southold Holiday Homes & Cottages (300+)