Southold cottages: Luxury cottages in Southold

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50 Holiday homes

Filters applied: Washing machine (1)

Travellers going to Southold are booking June dates now. Secure your holiday home today and have the perfect trip.

1 / 17

Southold holiday cottage rental

North Fork / Southold

2 6 14 nights min stay

Cottage / 2 bedrooms / sleeps 6 / 14 nights min stay

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from £276 / night

£1449 - £2207 / week

Book

from £276 / night

More results near

Distance approx 3.21 miles from Southold Show on Map

(4) Excellent 

1 / 14

Holiday apartment in Greenport

North Fork / Greenport

2 6 Min stay varies

Apartment / 2 bedrooms / sleeps 6 / Min stay varies

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from £207 / night

£1380 - £1845 / week

Book

from £207 / night

Distance approx 3.32 miles from Southold Show on Map

1 / 19

Holiday bungalow in Shelter Island

Hamptons / Shelter Island

3 6 Min stay varies

Bungalow / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £173 / night

£1035 / week

Book

from £173 / night

Distance approx 3.9 miles from Southold Show on Map

1 / 31

Holiday home with golf nearby in Shelter Island

Hamptons / Shelter Island

4 6 Min stay varies

House / 4 bedrooms / sleeps 6 / Min stay varies

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from £225 / night

£690 - £4690 / week

Book

from £225 / night

Distance approx 4.48 miles from Southold Show on Map

(7) Excellent 

1 / 18

Holiday cottage in Cutchogue

North Fork / Cutchogue

2 6 Min stay varies

Cottage / 2 bedrooms / sleeps 6 / Min stay varies

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from £104 / night

£656 - £1400 / week

Book

from £104 / night

Distance approx 4.51 miles from Southold Show on Map

1 / 8

Greenport holiday farmhouse accommodation

North Fork / Greenport

2 4 Min stay varies

Farmhouse / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £276 / night

£1932 - £2414 / week

Book

from £276 / night

Distance approx 4.52 miles from Southold Show on Map

1 / 16

Holiday farmhouse in Greenport

North Fork / Greenport

3 8 30 nights min stay

Farmhouse / 3 bedrooms / sleeps 8 / 30 nights min stay

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from £357 / night

£2495 / week

Book

from £357 / night

Distance approx 4.69 miles from Southold Show on Map

1 / 13

Holiday farmhouse rental

North Fork / Greenport

3 6 14 nights min stay

Farmhouse / 3 bedrooms / sleeps 6 / 14 nights min stay

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from £294 / night

£2052 / week

Book

from £294 / night

Distance approx 4.88 miles from Southold Show on Map

1 / 17

Holiday villa in Orosi

Province of Cartago / Orosi

2 4 3 nights min stay

Villa / 2 bedrooms / sleeps 4 / 3 nights min stay

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from £45 / night

£276 - £373 / week

Book

from £45 / night

Distance approx 5.01 miles from Southold Show on Map

1 / 11

Holiday home in Shelter Island

Hamptons / Shelter Island

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £247 / night

£1725 - £1863 / week

Book

from £247 / night

Distance approx 5.31 miles from Southold Show on Map

1 / 21

Holiday cottage in North Fork

Long Island / North Fork

4 8 14 nights min stay

Cottage / 4 bedrooms / sleeps 8 / 14 nights min stay

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from £237 / night

£1656 / week

Book

from £237 / night

Distance approx 5.91 miles from Southold Show on Map

(2) Excellent 

1 / 14

Home rental in East Marion

North Fork / East Marion

4 8 5 nights min stay

House / 4 bedrooms / sleeps 8 / 5 nights min stay

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from £241 / night

£1655 - £2041 / week

Book

from £241 / night

Distance approx 5.98 miles from Southold Show on Map

1 / 27

Holiday villa in Sag Harbor

Hamptons / Sag Harbor

5 10 Min stay varies

Villa / 5 bedrooms / sleeps 10 / Min stay varies

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from £1380 / night

£8276 / week

Book

from £1380 / night

Distance approx 5.99 miles from Southold Show on Map

(4) Excellent 

1 / 27

Sag Harbor holiday home rental

Hamptons / Sag Harbor

5 12 Min stay varies

House / 5 bedrooms / sleeps 12 / Min stay varies

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from £1035 / night

£7242 - £13518 / week

Book

from £1035 / night

Distance approx 6.11 miles from Southold Show on Map

1 / 16

Sag Harbor holiday home rental

Hamptons / Sag Harbor

3 7 7 nights min stay

House / 3 bedrooms / sleeps 7 / 7 nights min stay

Add to shortlist

from £828 / night

£5518 - £6207 / week

Book

from £828 / night

Distance approx 6.96 miles from Southold Show on Map

1 / 24

Holiday cottage in Southampton

Hamptons / Southampton

3 8 7 nights min stay

Cottage / 3 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £636 / night

£4449 / week

Book

from £636 / night

Distance approx 7.03 miles from Southold Show on Map

1 / 17

Home letting in Sag Harbor

Hamptons / Sag Harbor

4 6 Min stay varies

House / 4 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £986 / night

£6897 - £7621 / week

Book

from £986 / night

Distance approx 7.33 miles from Southold Show on Map

1 / 26

Holiday home in Sag Harbor

Hamptons / Sag Harbor

9 24 Min stay varies

House / 9 bedrooms / sleeps 24 / Min stay varies

Add to shortlist

from £1242 / night

£7449 - £24138 / week

Book

from £1242 / night

Distance approx 7.42 miles from Southold Show on Map

1 / 50

Mattituck holiday home accommodation

North Fork / Mattituck

5 10 1 night min stay

House / 5 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £380 / night

£2656 - £3138 / week

Book

from £380 / night

Distance approx 7.43 miles from Southold Show on Map

1 / 11

Holiday home rental

Hamptons / East Hampton

2 6 Min stay varies

House / 2 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £138 / night

£518 - £2069 / week

Book

from £138 / night

Distance approx 7.46 miles from Southold Show on Map

1 / 13

Sag Harbor holiday b&b rental

Hamptons / Sag Harbor

1 3 1 night min stay

B&B / 1 bedroom / sleeps 3 / 1 night min stay

Add to shortlist

from £173 / night

£1104 / week

Book

from £173 / night

Distance approx 7.54 miles from Southold Show on Map

1 / 16

Home rental in Southampton

Hamptons / Southampton

5 12 1 night min stay

House / 5 bedrooms / sleeps 12 / 1 night min stay

Add to shortlist

from £2414 / night

£9311 / week

Book

from £2414 / night

Distance approx 7.82 miles from Southold Show on Map

1 / 23

Sag Harbor holiday home rental

Hamptons / Sag Harbor

5 10 14 nights min stay

House / 5 bedrooms / sleeps 10 / 14 nights min stay

Add to shortlist

from £656 / night

£3104 - £7759 / week

Book

from £656 / night

Distance approx 8.08 miles from Southold Show on Map

(3) Very Good 

1 / 15

Home rental in Orient Bay with swimming pool

Saint-Martin / Orient Bay

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

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from £170 / night

£1424 / week

Book

from £170 / night

Distance approx 8.15 miles from Southold Show on Map

1 / 22

Holiday home with swimming pool in Bridgehampton

Hamptons / Bridgehampton

4 9 14 nights min stay

House / 4 bedrooms / sleeps 9 / 14 nights min stay

Add to shortlist

from £690 / night

£3449 - £8104 / week

Book

from £690 / night

Distance approx 8.15 miles from Southold Show on Map

1 / 26

Holiday cottage in Mattituck

North Fork / Mattituck

4 9 14 nights min stay

Cottage / 4 bedrooms / sleeps 9 / 14 nights min stay

Add to shortlist

from £273 / night

£1380 - £1725 / week

Book

from £273 / night

Distance approx 8.22 miles from Southold Show on Map

(4) Excellent 

1 / 21

Holiday apartment rental

Hamptons / Sag Harbor

2 5 Min stay varies

Apartment / 2 bedrooms / sleeps 5 / Min stay varies

Add to shortlist

from £204 / night

£1518 - £2035 / week

Book

from £204 / night

Distance approx 8.9 miles from Southold Show on Map

1 / 10

Apartment rental in Sag Harbor with swimming pool

Hamptons / Sag Harbor

1 8 30 nights min stay

Apartment / 1 bedroom / sleeps 8 / 30 nights min stay

Add to shortlist

from £1265 / night

£8851 / week

Book

from £1265 / night

Distance approx 8.9 miles from Southold Show on Map

1 / 18

Holiday home letting

Hamptons / Sag Harbor

4 8 30 nights min stay

House / 4 bedrooms / sleeps 8 / 30 nights min stay

Add to shortlist

from £1150 / night

£8046 / week

Book

from £1150 / night

Distance approx 8.94 miles from Southold Show on Map

1 / 20

Holiday villa with tennis court in Water Mill

Hamptons / Water Mill

7 10 7 nights min stay

Villa / 7 bedrooms / sleeps 10 / 7 nights min stay

Add to shortlist

from £1971 / night

£13793 / week

Book

from £1971 / night

Distance approx 9.29 miles from Southold Show on Map

1 / 10

Holiday cottage in Southampton

Hamptons / Southampton

3 6 Min stay varies

Cottage / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £242 / night

£2621 / week

Book

from £242 / night

Distance approx 9.53 miles from Southold Show on Map

1 / 13

Holiday apartment in Mattituck

North Fork / Mattituck

5 14 14 nights min stay

Apartment / 5 bedrooms / sleeps 14 / 14 nights min stay

Add to shortlist

from £104 / night

£725 / week

Book

from £104 / night

Distance approx 9.91 miles from Southold Show on Map

1 / 10

Holiday home in Sag Harbor

Hamptons / Sag Harbor

5 12 Min stay varies

House / 5 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £259 / night

£1725 - £1897 / week

Book

from £259 / night

Distance approx 9.92 miles from Southold Show on Map

1 / 22

Holiday villa in Southampton

Hamptons / Southampton

3 6 30 nights min stay

Villa / 3 bedrooms / sleeps 6 / 30 nights min stay

Add to shortlist

from £616 / night

£4311 / week

Book

from £616 / night

Distance approx 9.98 miles from Southold Show on Map

1 / 12

Holiday home in Bridgehampton

Hamptons / Bridgehampton

4 8 7 nights min stay

House / 4 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £690 / night

£4828 / week

Book

from £690 / night

Distance approx 10.14 miles from Southold Show on Map

1 / 21

Holiday home with swimming pool in Water Mill

Hamptons / Water Mill

4 10 5 nights min stay

House / 4 bedrooms / sleeps 10 / 5 nights min stay

Add to shortlist

from £794 / night

£5518 / week

Book

from £794 / night

Distance approx 10.27 miles from Southold Show on Map

1 / 21

Sagaponack holiday home rental

Hamptons / Sagaponack

5 10 14 nights min stay

House / 5 bedrooms / sleeps 10 / 14 nights min stay

Add to shortlist

from £1183 / night

£8276 / week

Book

from £1183 / night

Distance approx 10.54 miles from Southold Show on Map

(2) Very Good 

1 / 20

Holiday home in Bridgehampton

Hamptons / Bridgehampton

1 2 Min stay varies

House / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £94 / night

£518 / week

Book

from £94 / night

Distance approx 10.82 miles from Southold Show on Map

1 / 20

East Hampton holiday home rental

Hamptons / East Hampton

6 11 Min stay varies

House / 6 bedrooms / sleeps 11 / Min stay varies

Add to shortlist

from £789 / night

£5518 / week

Book

from £789 / night

Distance approx 10.82 miles from Southold Show on Map

1 / 10

Holiday home in East Hampton

Hamptons / East Hampton

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £966 / night

£3104 - £6207 / week

Book

from £966 / night

Distance approx 10.89 miles from Southold Show on Map

(1) Excellent 

1 / 25

Holiday home in Southampton

Hamptons / Southampton

6 12 Min stay varies

House / 6 bedrooms / sleeps 12 / Min stay varies

Add to shortlist

from £966 / night

£6759 - £10621 / week

Book

from £966 / night

Distance approx 10.98 miles from Southold Show on Map

(1) Excellent 

1 / 21

Holiday home with golf nearby in Southampton

Hamptons / Southampton

4 9 2 nights min stay

House / 4 bedrooms / sleeps 9 / 2 nights min stay

Add to shortlist

from £413 / night

£3104 - £3828 / week

Book

from £413 / night

Distance approx 11.41 miles from Southold Show on Map

(1) Very Good 

1 / 10

Holiday home in Water Mill

Hamptons / Water Mill

3 6 30 nights min stay

House / 3 bedrooms / sleeps 6 / 30 nights min stay

Add to shortlist

from £469 / night

£3449 / week

Book

from £469 / night

Distance approx 11.43 miles from Southold Show on Map

(2) Very Good 

1 / 100

Holiday home with swimming pool, golf nearby in East Hampton

Hamptons / East Hampton

5 10 Min stay varies

House / 5 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £238 / night

£1345 - £3656 / week

Book

from £238 / night

Distance approx 11.53 miles from Southold Show on Map

1 / 10

Holiday home in East Hampton

Hamptons / East Hampton

3 6 4 nights min stay

House / 3 bedrooms / sleeps 6 / 4 nights min stay

Add to shortlist

from £518 / night

£2621 / week

Book

from £518 / night

Distance approx 11.72 miles from Southold Show on Map

1 / 13

Home rental in East Hampton

Hamptons / East Hampton

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £414 / night

£2587 / week

Book

from £414 / night

Distance approx 11.9 miles from Southold Show on Map

(12) Excellent 

1 / 24

East Hampton holiday home rental

Hamptons / East Hampton

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £506 / night

£2414 / week

Book

from £506 / night

Distance approx 11.92 miles from Southold Show on Map

1 / 24

Southampton holiday home rental

Hamptons / Southampton

3 10 3 nights min stay

House / 3 bedrooms / sleeps 10 / 3 nights min stay

Add to shortlist

from £1104 / night

£5518 - £6725 / week

Book

from £1104 / night

Distance approx 12.09 miles from Southold Show on Map

1 / 24

Holiday townhouse in Southampton

Hamptons / Southampton

4 8 30 nights min stay

Townhouse / 4 bedrooms / sleeps 8 / 30 nights min stay

Add to shortlist

from £460 / night

£3219 / week

Book

from £460 / night

Distance approx 12.15 miles from Southold Show on Map

1 / 33

East Hampton holiday home rental

Hamptons / East Hampton

4 10 Min stay varies

House / 4 bedrooms / sleeps 10 / Min stay varies

Add to shortlist

from £345 / night

£2414 - £4483 / week

Book

from £345 / night

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