Holiday houses in Southold

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£203 Average

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37 Holiday homes

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

(12) Excellent 

1 / 25

Holiday home in Southold

North Fork / Southold

3 6 Min stay varies

House / 3 bedrooms / sleeps 6 / Min stay varies

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from £204 / night

£1207 - £3363 / week

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from £204 / night

More results near

Distance approx 3.6 miles from Southold Show on Map

1 / 20

Holiday home in Shelter Island

Hamptons / Shelter Island

3 4 7 nights min stay

House / 3 bedrooms / sleeps 4 / 7 nights min stay

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from £207 / night

£1449 / week

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from £207 / 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 4.5 miles from Southold Show on Map

(2) Very Good 

1 / 11

Holiday home rental

North Fork / Greenport

3 4 2 nights min stay

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

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from £128 / night

£794 - £1518 / week

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from £128 / 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

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from £357 / night

Distance approx 7.83 miles from Southold Show on Map

(3) Excellent 

1 / 10

Holiday cottage in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min stay

Cottage / 2 bedrooms / sleeps 4 / 2 nights min stay

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from £345 / night

£2414 / week

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from £345 / 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

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from £1265 / night

£8851 / week

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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

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from £1150 / night

£8046 / week

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from £1150 / 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

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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

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from £794 / night

£5518 / week

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from £794 / night

Distance approx 11.12 miles from Southold Show on Map

(1) Very Good 

1 / 9

Holiday apartment in Jamesport

North Fork / Jamesport

1 2 2 nights min stay

Apartment / 1 bedroom / sleeps 2 / 2 nights min stay

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from £173 / night

£1207 / week

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from £173 / 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

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from £469 / night

£3449 / week

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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

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from £238 / night

£1345 - £3656 / week

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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

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from £518 / night

£2621 / week

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from £518 / night

Distance approx 12.65 miles from Southold Show on Map

1 / 46

Holiday home in Hampton Bays

Hamptons / Hampton Bays

4 10 Min stay varies

House / 4 bedrooms / sleeps 10 / Min stay varies

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from £345 / night

£2318 - £3852 / week

Book

from £345 / night

Distance approx 13.12 miles from Southold Show on Map

1 / 13

Holiday cottage in East Hampton

Hamptons / East Hampton

1 2 2 nights min stay

Cottage / 1 bedroom / sleeps 2 / 2 nights min stay

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from £207 / night

£1242 / week

Book

from £207 / night

Distance approx 13.78 miles from Southold Show on Map

(5) Excellent 

1 / 28

Holiday home in Hampton Bays

Hamptons / Hampton Bays

4 8 2 nights min stay

House / 4 bedrooms / sleeps 8 / 2 nights min stay

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from £207 / night

£2069 / week

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from £207 / night

Distance approx 14.07 miles from Southold Show on Map

1 / 20

Home rental in East Hampton

Hamptons / East Hampton

2 4 3 nights min stay

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

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from £259 / night

£1725 / week

Book

from £259 / night

Distance approx 14.07 miles from Southold Show on Map

(3) Very Good 

1 / 7

B&b rental in East Hampton

Hamptons / East Hampton

1 2 Min stay varies

B&B / 1 bedroom / sleeps 2 / Min stay varies

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from £138 / night

£828 - £1035 / week

Book

from £138 / night

Distance approx 14.39 miles from Southold Show on Map

1 / 26

Holiday b&b in East Hampton

Hamptons / East Hampton

1 2 Min stay varies

B&B / 1 bedroom / sleeps 2 / Min stay varies

Add to shortlist

from £145 / night

£828 - £1035 / week

Book

from £145 / night

Distance approx 14.67 miles from Southold Show on Map

1 / 11

Holiday home in East Hampton

Hamptons / East Hampton

4 8 Min stay varies

House / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £863 / night

£1725 - £4138 / week

Book

from £863 / night

Distance approx 14.68 miles from Southold Show on Map

1 / 47

Home rental in East Hampton

Hamptons / East Hampton

3 7 Min stay varies

House / 3 bedrooms / sleeps 7 / Min stay varies

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from £294 / night

£1173 - £2690 / week

Book

from £294 / night

Distance approx 14.88 miles from Southold Show on Map

(1) Excellent 

1 / 18

Holiday home in East Hampton

Hamptons / East Hampton

6 16 Min stay varies

House / 6 bedrooms / sleeps 16 / Min stay varies

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from £621 / night

£3447 - £6207 / week

Book

from £621 / night

Distance approx 14.94 miles from Southold Show on Map

1 / 9

Holiday home in Old Saybrook

Connecticut / Old Saybrook

2 6 7 nights min stay

House / 2 bedrooms / sleeps 6 / 7 nights min stay

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from £138 / night

£887 / week

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from £138 / night

Distance approx 14.98 miles from Southold Show on Map

1 / 14

Hampton Bays holiday home rental

Hamptons / Hampton Bays

6 12 14 nights min stay

House / 6 bedrooms / sleeps 12 / 14 nights min stay

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from £690 / night

£4828 / week

Book

from £690 / night

Distance approx 15.11 miles from Southold Show on Map

(2) Very Good 

1 / 21

Holiday cottage in Old Saybrook

Connecticut / Old Saybrook

3 6 3 nights min stay

Cottage / 3 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £138 / night

£828 - £1311 / week

Book

from £138 / night

Distance approx 15.11 miles from Southold Show on Map

(1) Excellent 

1 / 33

Holiday home in Old Saybrook

Connecticut / Old Saybrook

3 8 Min stay varies

House / 3 bedrooms / sleeps 8 / Min stay varies

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from £173 / night

£690 - £18276 / week

Book

from £173 / night

Distance approx 16.13 miles from Southold Show on Map

1 / 22

Home rental in East Quogue with swimming pool

Hamptons / East Quogue

4 12 7 nights min stay

House / 4 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £690 / night

£4828 / week

Book

from £690 / night

Distance approx 16.91 miles from Southold Show on Map

1 / 11

Home rental in East Quogue

Hamptons / East Quogue

4 10 6 nights min stay

House / 4 bedrooms / sleeps 10 / 6 nights min stay

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from £345 / night

£2414 / week

Book

from £345 / night

Distance approx 17.13 miles from Southold Show on Map

(1) Excellent 

1 / 24

Holiday cottage in Old Lyme

Connecticut / Old Lyme

3 6 7 nights min stay

Cottage / 3 bedrooms / sleeps 6 / 7 nights min stay

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from £190 / night

£1104 / week

Book

from £190 / night

Distance approx 18.76 miles from Southold Show on Map

(2) Excellent 

1 / 30

Home rental in Quogue with swimming pool

Hamptons / Quogue

4 8 30 nights min stay

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

Add to shortlist

from £518 / night

£4138 / week

Book

from £518 / night

Distance approx 22.5 miles from Southold Show on Map

(2) Very Good 

1 / 13

Holiday home letting

Connecticut / Waterford

3 6 7 nights min stay

House / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £168 / night

£1173 / week

Book

from £168 / night

Distance approx 23.5 miles from Southold Show on Map

(5) Excellent 

1 / 22

Holiday home rental

Hamptons / Montauk

6 14 Min stay varies

House / 6 bedrooms / sleeps 14 / Min stay varies

Add to shortlist

from £397 / night

£2414 - £4483 / week

Book

from £397 / night

Distance approx 24.42 miles from Southold Show on Map

1 / 12

Holiday home in Montauk

Hamptons / Montauk

4 8 1 night min stay

House / 4 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £352 / night

£2138 / week

Book

from £352 / night

Distance approx 25.14 miles from Southold Show on Map

1 / 25

Holiday home in Westhampton Beach

New York / Westhampton Beach

3 8 4 nights min stay

House / 3 bedrooms / sleeps 8 / 4 nights min stay

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from £380 / night

£2759 / week

Book

from £380 / night

Distance approx 27.1 miles from Southold Show on Map

1 / 7

Montauk holiday cottage rental

Hamptons / Montauk

1 2 14 nights min stay

Cottage / 1 bedroom / sleeps 2 / 14 nights min stay

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from £148 / night

£1035 / week

Book

from £148 / night

Distance approx 27.14 miles from Southold Show on Map

(1) Excellent 

1 / 14

Holiday b&b in New London

Connecticut / New London

1 2 2 nights min stay

B&B / 1 bedroom / sleeps 2 / 2 nights min stay

Add to shortlist

from £66 / night

£394 / week

Book

from £66 / night

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