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Holiday Lettings
> Europe
> United Kingdom
> England
> Yorkshire
> North Yorkshire
> Cottages and houses in Helmsley

Cottages in Helmsley and Houses - Holiday Lettings - Holiday Rentals Helmsley

Price per night

£1 £750 -

Bedrooms

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  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Apartment (1)
  • Cottage (17)
  • Barn (2)

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20 Holiday homes

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Great rentals within 20 miles that match your search

Holiday cottage with golf nearby in Ampleforth

Ampleforth cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3
14 reviews

from £103 / night

£458 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday barn in Knayton

Knayton barn

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
12 reviews

from £92 / night

£642 / week

1 / 12

Great rentals within 20 miles that match your search

Cottage rental in Sowerby

Sowerby cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £115 / night

£802 / week

1 / 10

Great rentals within 20 miles that match your search

Great Ayton holiday cottage let

Great Ayton cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8
25 reviews

from £126 / night

£662 - £1,023 / week

1 / 12

Great rentals within 20 miles that match your search

Cottage rental in Pickering

Pickering cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8
4 reviews

from £212 / night

£977 - £2,042 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday cottage in Glaisdale

Glaisdale cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
7 reviews

from £229 / night

£1,546 / week

1 / 25

Great rentals within 20 miles that match your search

Holiday cottage in Glaisdale

Glaisdale cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
5 reviews

from £229 / night

£1,546 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday apartment in Easingwold

Easingwold apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £126 / night

£882 / week

1 / 18

Great rentals within 20 miles that match your search

Cottage accommodation in Pickering

Pickering cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7
8 reviews

from £187 / night

£905 - £1,608 / week

1 / 24

Great rentals within 20 miles that match your search

Pickering holiday cottage rental

Pickering cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £142 / night

£655 - £1,316 / week

1 / 13

Great rentals within 20 miles that match your search

Lealholm holiday barn rental

Lealholm barn

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £134 / night

£516 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday cottage in Whitby

Whitby cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from £138 / night

£687 / week

1 / 8

Great rentals within 20 miles that match your search

Cottage rental in Hutton le Hole

Hutton le Hole cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
30 reviews

from £189 / night

£1,203 / week

1 / 28

Great rentals within 20 miles that match your search

Glaisdale holiday cottage rental

Glaisdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2
5 reviews

from £224 / night

£1,563 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday cottage in Lastingham

Lastingham cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
3 reviews

from £132 / night

£796 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday cottage letting

Pickering cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
2 reviews

from £121 / night

£555 - £1,066 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday cottage rental

Danby cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
29 reviews

from £275 / night

£1,924 - £2,508 / week

1 / 18

Great rentals within 20 miles that match your search

Malton holiday cottage rental

Malton cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
8 reviews

from £144 / night

£905 - £1,626 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday cottage in Pickering

Pickering cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5
3 reviews

from £142 / night

£655 - £1,316 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday cottage in Danby

Danby cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6
42 reviews

from £275 / night

£1,924 - £2,508 / week

1 / 28

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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York holiday home rental

York house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Walking holidays

4 reviews

from £287 / night

£1,718 / week

1 / 22

Great rentals within 20 miles that match your search

Cottage accommodation in Gillamoor

Gillamoor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Walking holidays

32 reviews

from £264 / night

£1,406 / week

1 / 28

Great rentals within 20 miles that match your search

Cottage rental in Kirby Misperton

Kirby Misperton cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Tennis in town

34 reviews

from £166 / night

£653 - £1,014 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday apartment in Hutton le Hole

Hutton le Hole apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Tennis in town

39 reviews

from £98 / night

£510 - £739 / week

1 / 12

Great rentals within 20 miles that match your search

Cottage rental in Flaxton

Flaxton cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Tennis in town

from £126 / night

£676 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday cottage rental

Glaisdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 10

1 filter does not match: Tennis in town

10 reviews

from £287 / night

£1,603 - £3,206 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday home rental

Appleton le Moors house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

1 filter does not match: Tennis in town

85 reviews

from £485 / night

£5,330 / week

1 / 24

Great rentals within 20 miles that match your search

Tollerton holiday barn rental

Tollerton barn

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

1 filter does not match: Walking holidays

15 reviews

from £516 / night

£3,321 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday cottage in Chop Gate

Chop Gate cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Tennis in town

8 reviews

from £89 / night

£619 / week

1 / 25

Great rentals within 20 miles that match your search

Cottage rental in Castleton

Castleton cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Tennis in town

121 reviews

from £103 / night

£516 - £630 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday lodge in Castleton

Castleton lodge

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Tennis in town

16 reviews

from £102 / night

£504 - £628 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday cottage in Chop Gate

Chop Gate cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Tennis in town

10 reviews

from £72 / night

£503 / week

1 / 23

Great rentals within 20 miles that match your search

Pickering holiday cottage rental

Pickering cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Tennis in town

8 reviews

from £99 / night

£689 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday cottage in York

York cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Tennis in town

37 reviews

from £81 / night

£481 - £1,111 / week

1 / 17

Great rentals within 20 miles that match your search

York holiday cottage rental

York cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Walking holidays

2 reviews

from £138 / night

£1,088 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday lodge in Malton

Malton lodge

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Tennis in town

18 reviews

from £224 / night

£1,563 / week

1 / 30

Great rentals within 20 miles that match your search

Home accommodation in Helmsley with golf nearby

Helmsley house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Walking holidays

1 review

from £194 / night

£581 - £1,847 / week

1 / 27

Great rentals within 20 miles that match your search

Ainthorpe holiday home rental

Ainthorpe house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13

1 filter does not match: Walking holidays

from £475 / night

£1,615 - £6,096 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday lodge in Malton

Malton lodge

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Tennis in town

from £218 / night

£1,523 / week

1 / 17

Great rentals within 20 miles that match your search

Home rental in Carlton-in-Cleveland with golf nearby

Carlton-in-Cleveland house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Walking holidays

from £332 / night

£1,149 - £2,469 / week

1 / 52

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