20 Best Vacation Rentals in Helmsley - Holiday Lettings - Cabins

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21 Vacation rentals

(4) Excellent 

22

Vacation barn in Helmsley

North Yorkshire / Helmsley

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
The Stables is nestled in the beautiful North Yorkshire countryside between the edge of the North Yorkshire Moors and the Howardian Hills, just 4 miles outside the pretty market town of Helmsley and under an hour away from the diverse North Yorkshire coastline or the hi …see more

from $116 / night

$494 - $949 / week

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from $116 / night

(2) Excellent 

10

Vacation cottage in Helmsley

North Yorkshire / Helmsley

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Ivy cottage is situated overlooking a pleasant green a two minute walk from Helmsley town centre. The accommodation is suitable for all ages. The cottage has three bedrooms, a double, twin and a single. The bathroom has recently been refurbished. There is a conservatory …see more

from $89 / night

$441 - $890 / week

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from $89 / night

(4) Excellent 

19

Vacation cottage in Helmsley

North Yorkshire / Helmsley

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Private garden
Friday or Monday start for weekly stays. Short breaks are Fri-Mon (3 nights) and Mon-Fri (4 nights) only. One bedroom barn conversion set within the North York Moors National Park in the valley of Bilsdale. This south facing 200 year old character property has been ta …see more

from $102 / night

$538 - $762 / week

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from $102 / night

(7) Excellent 

Certificate of Excellence

10

Caravan/mobile home rental in Helmsley

North Yorkshire / Helmsley

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 50 mi
  • Child friendly
  • Private garden
High Farm, Beadlam Rigg is located within the North York Moors National Park, just off the A170 which runs between Helmsley and Scarborough, 4 miles from Helmsley & 6 miles from Kirkbymoorside. We are a family friendly site, ideally located for exploring the nearby mark …see more

Certificate of Excellence

from $64 / night

$448 - $628 / week

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from $64 / night

9

Vacation home in Helmsley

North Yorkshire / Helmsley

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
COSY COTTAGE CENTRALLY LOCATED IN A DELIGHTFUL ENGLISH TOWN Nestling close to the 12th century market place square, the property is the perfect hideaway for your stay in Helmsley, offering superb accommodation just moments away from local facilities. Located on th …see more

from $61 / night

$427 - $936 / week

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from $61 / night

13

Vacation cottage in Helmsley

North Yorkshire / Helmsley

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
LOVELY STONE COTTAGE WITH LARGE GARDEN This traditional stone terraced cottage has been refurbished to a high standard throughout, situated in the picturesque market town of Helmsley with a large enclosed garden. Superbly presented, the cottage has 21st century luxur …see more

from $95 / night

$664 - $1419 / week

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from $95 / night

(1) Excellent 

8

Vacation home in Helmsley

North Yorkshire / Helmsley

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Frankel cottage is located 0.9 miles from the centre of Helmsley a busy market town where you will find many pubs & shops selling local produce. Frankel cottage has recently been fully refurbished with a new kitchen, bathroom flooring and furniture. The kitchen has an e …see more

from $167 / night

$896 - $1024 / week

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from $167 / night

(2) Excellent 

15

Vacation yurt in Nawton

Helmsley / Nawton

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Canadian Fields is located within the North York Moors National Park, just off the A170 which runs between Helmsley and Scarborough, 3 miles from Helmsley & 3 miles from Kirkbymoorside. We are a family friendly site, ideally located for exploring the nearby market town …see more

from $154 / night

$717 / week

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from $154 / night

(1) Excellent 

16

Vacation home rental

North Yorkshire / Helmsley

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
The house is fully furnished with TV, Wi-Fi, BT Vision, DVD player, CD player: comprising three reception rooms, two double bedrooms and a twin bedroom. Overall it can easily accommodate 6 people. The master bedroom has oak furniture and a wood burning stove. All linen …see more

from $76 / night

$527 - $1625 / week

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from $76 / night

11

Home accommodation in Helmsley

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
This mid-terrace cottage is in the market town of Helmsley near to Kirkbymoorside and can sleep four people in two bedrooms. 8 Pottergate Mews is a lovely mid-terrace cottage situated in the market town of Helmsley just six miles from Kirkbymoorside, North Yorkshire. …see more

from $79 / night

$546 - $1531 / week

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from $79 / night

(1) Excellent 

12

Vacation home in Helmsley

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
This charming cottage sits in the market town of Helmsley in North Yorkshire, sleeping four people in two bedrooms. Coronation Cottage is a stone-built cottage tucked away in a central position in the market town of Helmsley, North Yorkshire. With two bedrooms, includi …see more

from $53 / night

$367 - $971 / week

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from $53 / night

(3) Excellent 

14

Home rental in Nawton

Helmsley / Nawton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Pet friendly
This super, end-terrace cottage in Nawton, North Yorkshire, sleeps five people in three bedrooms. Archway House is a charming, end-terrace cottage next to the owner's other holiday home, in the North Yorkshire village of Nawton. With three bedrooms including a fantasti …see more

from $57 / night

$387 - $1096 / week

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from $57 / night

9

Vacation home in Helmsley

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
This attractive, end-terrace, stone-built mews cottage is in the market town of Helmsley, and can sleep four people in two bedrooms. Red Grouse Cottage is an attractive, end-terrace, stone-built mews cottage, quietly tucked away within a five minute walk to the centre …see more

from $53 / night

$368 - $975 / week

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from $53 / night

(4) Very Good 

13

Vacation home in Helmsley

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
This two bedroom house is able to sleep up to four people and is located close to the village of Helmsley. This traditional, stone-built, cottage is a semi-detached property that adjoins the owner's house on a working livestock farm near Old Byland. Just seven miles fr …see more

from $45 / night

$310 - $981 / week

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from $45 / night

(2) Excellent 

10

Vacation home rental

North Yorkshire / Helmsley

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
This charming, detached stone cottage, set in a hamlet close to the North Yorkshire market town of Helmsley, can sleep two people in one double bedroom. Peg's Cottage, a delightful, detached, stone cottage, is set solely over the ground floor in a little hamlet just tw …see more

from $48 / night

$332 - $634 / week

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from $48 / night

16

Helmsley Vacation home rental

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Pet friendly
This barn conversion is in the hamlet of Chop Gate, ten miles from Helmsley and sleeps four people in two bedrooms. Clack Cat Cottage is a Grade II listed barn conversion, one of three, in the hamlet of Chop Gate, ten miles from Helmsley which sleeps four people in two …see more

from $64 / night

$442 - $1115 / week

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from $64 / night

6

Helmsley Vacation home rental

North Yorkshire / Helmsley

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Pet friendly
This ground floor barn conversion is located in the hamlet of Chop Gate between Helmsley and Stokesley in North Yorkshire and can sleep two people in one bedroom. Owl Cottage is a terraced barn conversion cottage on a working farm in the tiny hamlet of Chop Gates, ten …see more

from $49 / night

$340 - $792 / week

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from $49 / night

11

Helmsley Vacation home rental

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Pet friendly
This ground floor barn conversion is located in the hamlet of Chop Gate between Helmsley and Stokesley in North Yorkshire and can sleep four people in two bedrooms. Witches Cottage is a terraced barn conversion cottage on a working farm in the tiny hamlet of Chop Gate …see more

from $62 / night

$424 - $1065 / week

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from $62 / night

15

Helmsley Vacation home rental

North Yorkshire / Helmsley

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
This end-terrace cottage is located in Helmsley and can sleep five people in three bedrooms. Ivy Cottage is a delightful end-terrace cottage overlooking a village green close to the centre of Helmsley in the North York Moors National Park. The cottage sleeps five peopl …see more

from $64 / night

$441 - $1263 / week

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from $64 / night

(2) Good 

15

Vacation home in Helmsley

North Yorkshire / Helmsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
This stone-built mews cottage is situated in a quiet part of Helmsley in the North York Moors National Park and can sleep four people in two bedrooms. Mews Cottage is a stone-built mews cottage situated in a quiet part of Helmsley in the North York Moors National Park …see more

from $62 / night

$424 - $978 / week

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from $62 / night

(22) Excellent 

23

Vacation home in Helmsley

North Yorkshire / Helmsley

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Child friendly
  • Pet friendly
With four spacious, sunny bedrooms – able to sleep a total of eleven people – this property is best suited to larger groups and families. Just a few minutes walk from the centre of the pretty market town of Helmsley is this charming property - a superb, semi-detached h …see more

from $99 / night

$683 - $2155 / week

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from $99 / night

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