COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals

Helmsley Vacation Rentals & Homes - 331 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

331 Vacation rentals

(26)

1 / 22

Helmsley House

  • 4
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$277.00

Excellent (26 reviews)

Inquire

from $277.00 / night

1 / 14

Hawnby House

  • 2
  • 4
  • 3 nights min
  • Pet friendly

$192.00

Inquire

from $192.00 / night

(1)

1 / 15

Helmsley House

  • 2
  • 4
  • 3 nights min
  • Child friendly

$228.00

Excellent (1 reviews)

Inquire

from $228.00 / night

(7)

1 / 9

Nawton House

  • 1
  • 2
  • 3 nights min
  • Child friendly
  • Pet friendly

$135.00

Very Good (7 reviews)

Inquire

from $135.00 / night

(4)

1 / 12

Helmsley House

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly

$103.00

Very Good (4 reviews)

Inquire

from $103.00 / night

(4)

1 / 11

Helmsley House

  • 2
  • 4
  • 3 nights min
  • Child friendly

$124.00

Excellent (4 reviews)

Inquire

from $124.00 / night

1 / 13

Helmsley House

  • 4
  • 8
  • 3 nights min
  • Child friendly
  • Private garden

$233.00

Inquire

from $233.00 / night

1 / 12

Helmsley House

  • 3
  • 5
  • 3 nights min
  • Child friendly

$147.00

Inquire

from $147.00 / night

1 / 28

Scawton Cottage

  • 1
  • 2
  • 3 nights min
  • Pet friendly

$120.00

Inquire

from $120.00 / night

1 / 29

Scawton Cottage

  • 1
  • 2
  • 3 nights min
  • Pet friendly

$120.00

Inquire

from $120.00 / night

(3)

1 / 20

Nawton Yurt

  • 1
  • 2
  • 3 nights min
  • Child friendly
  • Private garden

$110.00

Excellent (3 reviews)

Inquire

from $110.00 / night

1 / 15

Nawton Log cabin

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$165.00

Inquire

from $165.00 / night

1 / 13

Helmsley Cottage

  • 2
  • 4
  • 3 nights min
  • Private garden

$194.00

Inquire

from $194.00 / night

1 / 23

Nawton House

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$118.00

Inquire

from $118.00 / night

1 / 21

Helmsley Cottage

  • 2
  • 4
  • 3 nights min
  • Pet friendly
  • Private garden

$128.00

Inquire

from $128.00 / night

Your search has been expanded 19.6 miles to include more rentals

(6)

1 / 8

East Heslerton House - 18 miles away

  • 2
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$177.00

Excellent (6 reviews)

Inquire

from $177.00 / night

(5)

1 / 8

East Heslerton House - 18 miles away

  • 2
  • 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$155.00

Very Good (5 reviews)

Inquire

from $155.00 / night

(8)

1 / 18

West Heslerton House - 18 miles away

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$290.00

Excellent (8 reviews)

Inquire

from $290.00 / night

1 / 17

West Heslerton Cottage - 18.1 miles away

  • 1
  • 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$139.00

Inquire

from $139.00 / night

1 / 12

Clifton Apartment - 19.4 miles away

  • 1
  • 2
  • 3 nights min
  • Child friendly

$120.00

Inquire

from $120.00 / night

1 / 12

Clifton Apartment - 19.4 miles away

  • 1
  • 2
  • 3 nights min

$135.00

Inquire

from $135.00 / night

1 / 20

Stonegrave Cottage - 5 miles away

  • 3
  • 6
  • 3 nights min
  • Pet friendly
  • Private garden

$181.00

Inquire

from $181.00 / night

(1)

1 / 9

Kirkbymoorside Cottage - 5.4 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$146.00

Excellent (1 reviews)

Inquire

from $146.00 / night

(1)

1 / 19

Sheriff Hutton Log cabin - 11.4 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly

$333.00

Excellent (1 reviews)

Inquire

from $333.00 / night

1 / 9

Pickering Cottage - 11 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$158.00

Inquire

from $158.00 / night

1 / 19

Danby Cottage - 16.5 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$188.00

Inquire

from $188.00 / night

1 / 19

Kirkbymoorside Apartment - 5.5 miles away

  • 3
  • 4
  • 3 nights min

$178.00

Inquire

from $178.00 / night

1 / 16

Gillamoor Cottage - 5.8 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$169.00

Inquire

from $169.00 / night

1 / 18

Pickering Cottage - 10.9 miles away

  • 2
  • 3
  • 3 nights min
  • Private garden

$143.00

Inquire

from $143.00 / night

1 / 9

Grosmont Cottage - 18.9 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$210.00

Inquire

from $210.00 / night

1 / 17

Ainthorpe Cottage - 16.1 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Private garden

$141.00

Inquire

from $141.00 / night

1 / 20

Thornton-Le-Dale Cottage - 14 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$143.00

Inquire

from $143.00 / night

1 / 9

Egton Cottage - 19 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Pet friendly

$258.00

Inquire

from $258.00 / night

1 / 9

Grosmont Cottage - 18.9 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly

$210.00

Inquire

from $210.00 / night

1 / 21

Malton Cottage - 13.1 miles away

  • 2
  • 4
  • 3 nights min

$183.00

Inquire

from $183.00 / night

1 / 16

Grosmont Cottage - 18.9 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$210.00

Inquire

from $210.00 / night

(1)

1 / 16

Glaisdale Cottage - 17 miles away

  • 2
  • 3
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$157.00

Very Good (1 reviews)

Inquire

from $157.00 / night

1 / 19

Kildale Cottage - 16.2 miles away

  • 3
  • 6
  • 3 nights min
  • Pet friendly
  • Private garden

$172.00

Inquire

from $172.00 / night

1 / 21

Old Malton Log cabin - 12.3 miles away

  • 2
  • 4
  • 3 nights min
  • Private garden

$181.00

Inquire

from $181.00 / night

1 / 9

Loftus Cottage - 19.6 miles away

  • 3
  • 6
  • 3 nights min
  • Pet friendly
  • Private garden

$165.00

Inquire

from $165.00 / night