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 2-bedroom Vacation Rentals, Homes & More - 247 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

247 Vacation rentals

Filters applied: 2+ Bedrooms

(26)

1 / 22

Helmsley House

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

$264.00

Excellent (26 reviews)

Inquire

from $264.00 / night

1 / 14

Hawnby House

  • 2
  • 4
  • 3 nights min
  • Pet friendly

$141.00

Inquire

from $141.00 / night

(1)

1 / 15

Helmsley House

  • 2
  • 4
  • 3 nights min
  • Child friendly

$204.00

Excellent (1 reviews)

Inquire

from $204.00 / night

(5)

1 / 22

Nawton House

  • 2
  • 4
  • 3 nights min
  • Child friendly

$140.00

Excellent (5 reviews)

Inquire

from $140.00 / night

(4)

1 / 12

Helmsley House

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

$98.00

Very Good (4 reviews)

Inquire

from $98.00 / night

(4)

1 / 11

Helmsley House

  • 2
  • 4
  • 3 nights min
  • Child friendly

$118.00

Excellent (4 reviews)

Inquire

from $118.00 / night

1 / 13

Helmsley House

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

$221.00

Inquire

from $221.00 / night

1 / 12

Helmsley House

  • 3
  • 5
  • 3 nights min
  • Child friendly

$140.00

Inquire

from $140.00 / night

(4)

1 / 19

Nawton House

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$158.00

Excellent (4 reviews)

Inquire

from $158.00 / night

1 / 21

Helmsley Cottage

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

$125.00

Inquire

from $125.00 / night

Your search has been expanded 19.8 miles to include more rentals

1 / 15

Thornton-Le-Dale House - 14.7 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly

$156.00

Inquire

from $156.00 / night

1 / 18

Thornton-Le-Dale House - 14.7 miles away

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

$192.00

Inquire

from $192.00 / night

1 / 15

Great Habton Log cabin - 10.1 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Private garden

$164.00

Inquire

from $164.00 / night

1 / 20

Strensall House - 14.3 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly

$209.00

Inquire

from $209.00 / night

(6)

1 / 18

Pickering House - 13 miles away

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

$160.00

Very Good (6 reviews)

Inquire

from $160.00 / night

(5)

1 / 13

Newton-on-Rawcliffe House - 13 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly

$146.00

Very Good (5 reviews)

Inquire

from $146.00 / night

(2)

1 / 14

Hutton le Hole House - 6.9 miles away

  • 2
  • 5
  • 3 nights min
  • Pet friendly
  • Private garden

$146.00

Excellent (2 reviews)

Inquire

from $146.00 / night

(11)

1 / 24

Rosedale Abbey House - 10 miles away

  • 4
  • 8
  • 3 nights min
  • Child friendly
  • Pet friendly

$279.00

Very Good (11 reviews)

Inquire

from $279.00 / night

(7)

1 / 11

Thornton-Le-Dale House - 14.1 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$267.00

Very Good (7 reviews)

Inquire

from $267.00 / night

(2)

1 / 12

Great Ouseburn House - 17.1 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly

$161.00

Excellent (2 reviews)

Inquire

from $161.00 / night

(10)

1 / 13

Kirkbymoorside House - 5.5 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$245.00

Excellent (10 reviews)

Inquire

from $245.00 / night

(2)

1 / 13

Lastingham House - 8.3 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$120.00

Very Good (2 reviews)

Inquire

from $120.00 / night

(5)

1 / 23

Stamford Bridge House - 18.7 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$192.00

Excellent (5 reviews)

Inquire

from $192.00 / night

1 / 9

Hutton le Hole House - 6.8 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$176.00

Inquire

from $176.00 / night

(6)

1 / 8

East Heslerton House - 18 miles away

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

$148.00

Excellent (6 reviews)

Inquire

from $148.00 / night

(8)

1 / 18

West Heslerton House - 18 miles away

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

$229.00

Excellent (8 reviews)

Inquire

from $229.00 / night

(10)

1 / 8

Guisborough House - 19.2 miles away

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

$137.00

Excellent (10 reviews)

Inquire

from $137.00 / night

(5)

1 / 8

East Heslerton House - 18 miles away

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

$130.00

Very Good (5 reviews)

Inquire

from $130.00 / night

(8)

1 / 31

Ebberston House - 19 miles away

  • 8
  • 17
  • 3 nights min
  • Pet friendly
  • Private garden

$518.00

Very Good (8 reviews)

Inquire

from $518.00 / night

(18)

1 / 12

Pickering House - 11.4 miles away

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

$129.00

Excellent (18 reviews)

Inquire

from $129.00 / night

(2)

1 / 9

Castleton House - 16 miles away

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

$197.00

Excellent (2 reviews)

Inquire

from $197.00 / night

1 / 14

Pickering House - 11.5 miles away

  • 3
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$144.00

Inquire

from $144.00 / night

(2)

1 / 17

Kilburn House - 6.7 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly

$185.00

Excellent (2 reviews)

Inquire

from $185.00 / night

(3)

1 / 9

Kirby Misperton House - 11.8 miles away

  • 2
  • 4
  • 3 nights min
  • Private garden

$114.00

Excellent (3 reviews)

Inquire

from $114.00 / night

(4)

1 / 29

Skirpenbeck House - 18.7 miles away

  • 3
  • 6
  • 3 nights min
  • Child friendly

$285.00

Excellent (4 reviews)

Inquire

from $285.00 / night

(2)

1 / 22

Grosmont House - 19.8 miles away

  • 2
  • 5
  • 3 nights min
  • Child friendly
  • Pet friendly

$153.00

Very Good (2 reviews)

Inquire

from $153.00 / night

(2)

1 / 16

Glaisdale House - 17 miles away

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

$125.00

Very Good (2 reviews)

Inquire

from $125.00 / night

1 / 11

Great Ayton House - 15.7 miles away

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

$164.00

Inquire

from $164.00 / night

(1)

1 / 16

Danby House - 18.9 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$152.00

Excellent (1 reviews)

Inquire

from $152.00 / night

1 / 15

Bulmer House - 12.1 miles away

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

$101.00

Inquire

from $101.00 / night