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

$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

$227.00

Excellent (1 reviews)

Inquire

from $227.00 / 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 / 13

Helmsley Cottage

  • 2
  • 4
  • 3 nights min
  • Private garden

$193.00

Inquire

from $193.00 / night

1 / 23

Nawton House

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

$118.00

Inquire

from $118.00 / night

1 / 15

Nawton Log cabin

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

$165.00

Inquire

from $165.00 / 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 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 / 25

Sinnington Cottage - 8.2 miles away

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

$215.00

Inquire

from $215.00 / 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 / 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

$156.00

Very Good (1 reviews)

Inquire

from $156.00 / night

1 / 12

Swainby Cottage - 14.1 miles away

  • 2
  • 3
  • 3 nights min
  • Pet friendly

$122.00

Inquire

from $122.00 / night

(2)

1 / 20

Stokesley Cottage - 16.4 miles away

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

$137.00

Excellent (2 reviews)

Inquire

from $137.00 / night

1 / 19

Glaisdale Cottage - 17 miles away

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

$162.00

Inquire

from $162.00 / night

1 / 19

Kildale Cottage - 16.2 miles away

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

$171.00

Inquire

from $171.00 / night

1 / 9

Egton Cottage - 19 miles away

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

$257.00

Inquire

from $257.00 / night

(3)

1 / 25

Pickering Cottage - 11.2 miles away

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

$132.00

Excellent (3 reviews)

Inquire

from $132.00 / night

1 / 18

Boroughbridge Apartment - 17.9 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly

$137.00

Inquire

from $137.00 / night

1 / 27

Ampleforth Cottage - 3.8 miles away

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

$193.00

Inquire

from $193.00 / night

1 / 24

Hutton Rudby Cottage - 16.6 miles away

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

$114.00

Inquire

from $114.00 / night

1 / 11

Great Ayton Cottage - 15.7 miles away

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

$185.00

Inquire

from $185.00 / night

1 / 13

Amotherby Log cabin - 10.1 miles away

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$185.00

Inquire

from $185.00 / night

1 / 17

Great Ayton Cottage - 15.7 miles away

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

$171.00

Inquire

from $171.00 / night

(10)

1 / 100

Hutton Rudby House - 16.5 miles away

  • 13
  • 20
  • 3 nights min
  • Child friendly
  • Private garden

$2,308.00

Excellent (10 reviews)

Inquire

from $2,308.00 / night

1 / 28

Stamford Bridge House - 18.6 miles away

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

$337.00

Inquire

from $337.00 / night

1 / 15

Sowerby Cottage - 11.4 miles away

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

$124.00

Inquire

from $124.00 / night

1 / 33

Carlton-in-Cleveland House - 14.1 miles away

  • 7
  • 12
  • 3 nights min
  • Child friendly
  • Private garden

$411.00

Inquire

from $411.00 / night

1 / 24

Amotherby Log cabin - 10 miles away

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

$270.00

Inquire

from $270.00 / night

1 / 20

Boroughbridge Cottage - 17.3 miles away

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

$177.00

Inquire

from $177.00 / night

1 / 21

Malton Cottage - 12.9 miles away

  • 4
  • 7
  • 3 nights min
  • Private garden

$227.00

Inquire

from $227.00 / night

1 / 8

West Heslerton House - 18.1 miles away

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

$163.00

Inquire

from $163.00 / night

1 / 25

Knayton Cottage - 12.4 miles away

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

$129.00

Inquire

from $129.00 / night

(1)

1 / 18

Ebberston House - 17.6 miles away

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

$165.00

Excellent (1 reviews)

Inquire

from $165.00 / night