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37 Holiday homes in Helmsley

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37 Results  |  
12 Photos

Cottage | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £52 /night

£359 - £557 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
Detached barn conversion in rural location within the stunning valley of Bilsdale in the North York Moors. Private south facing garden. Romantic get away for couples. Wood burning stove and vaulted beam ceilings add to the charm. Short breaks available all year. WiFi provided free of charge. Garden has a patio area and wooden table and 4 chairs.  …see more

15 Photos

Townhouse | 3 Bedrooms | sleeps 7

Excellent 5/5 

3 Nights min stay

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from £88 /night

£610 - £928 / week

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Key info:

  • Nearest beach 48 km
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
A beautiful spacious Grade II Listed 3/4 storey Georgian Town House, just off the market square in the delightful 12th century market town of Helmsley, on the edge of the North Yorkshire Moors National Park. The property has 3 bedrooms and 3 bathrooms - sleeping 2-7 WIFI included  …see more

6 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

3 Nights min stay

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from £72 /night

£504 - £557 / week

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Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
  • Private garden
The cottage is decorated to a high standard and is situated in a "honey pot" position within this beautiful historic town. You can enjoy log fires in the winter and beautiful gardens in the summer to soak up your day. Rosebeck provides you with comfort and location. The accommodation is set to suit both families and couples having 2 beds and baths. There is wifi if needed  …see more

Featured properties

8 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £37 /night

£259 - £670 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Standing peacefully in a small development, this stone mews holiday cottage enjoys a light, airy open plan living area, contemporary furnishings, small enclosed garden and private parking. Within easy walking distance of Helmsley's market square and its wealth of qua...  …see more

7 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £39 /night

£273 - £624 / week

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Key info:

  • Not suitable for children
  • No pets allowed
An 18th-century beamed holiday cottage with lawned private garden situated in a quiet backwater of this pretty bustling little market town noted for its castle ruins. Visit the gardens of Duncombe Park (open June-August). Helmsley lies on the edge of the North York M...  …see more

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £41 /night

£286 - £636 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well-equipped holiday cottages (refs W43183, W43184 and W43185) stand in a landscaped courtyard, close to the own...  …see more

15 Photos

House | 2 Bedrooms | sleeps 4

Short stays welcome

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from £38 /night

£265 - £598 / week

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Key info:

  • Suitable for children over
  • No pets allowed
  • Private garden
This charming cottage sits in the market town of Helmsley in North Yorkshire, sleeping four people in two bedrooms.  …see more

23 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £108 /night

£754 - £1804 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Garth Cottage is one of five stone-built properties in an exclusive development, forming a delightful crescent in the picturesque market town of Helmsley. Situated behind the Church of All Saints and opposite Cannon Garth, an old religious house dating back to mediev...  …see more

18 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £65 /night

£451 - £995 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well equipped holiday cottages stand in a landscaped courtyard, close to the owners' farmhouse. Guests can enjoy ...  …see more

16 Photos

Cottage | 4 Bedrooms | sleeps 11

Excellent 5/5 

Short stays welcome

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from £69 /night

£483 - £1257 / week

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Key info:

  • Suitable for children over
  • Car advised
  • Pets welcome
  • Private garden
With four spacious, sunny bedrooms – able to sleep a total of eleven people – this property is best suited to larger groups and families.  …see more

10 Photos

Cottage | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £34 /night

£234 - £580 / week

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Key info:

  • Nearest beach 0 km
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
This two bedroom house is able to sleep up to four people and is located close to the village of Helmsley.  …see more

9 Photos

House | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £45 /night

£312 - £902 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Set within a large private garden with country views, this detached stone house lies at the edge of the village, within the North York Moors National Park. An excellent area for walking, cycling or riding, with a wide network of footpaths. Market town of Helmsley, 4 ...  …see more

15 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £89 /night

£623 - £1429 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Birchglow lies in the heart of the delightful market town of Helmsley. One of five stone-built homes, it is adjacent to the renowned Feversham Arms Hotel and Verbena Spa where day passes are available, beautifully furnished with good quality fittings and appliances. ...  …see more

17 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £55 /night

£381 - £765 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well equipped holiday cottages stand in a landscaped courtyard, close to the owners' farmhouse. Guests can enjoy ...  …see more

7 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £47 /night

£324 - £606 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This character holiday cottage, situated in a village between the market towns of Helmsley and Kirbymoorside, both 3 miles, is in a perfect location for enjoying the North York Moors. Whitby, 22 miles, with sandy beach and harbour. York, 26 miles. Pickering, home of ...  …see more

11 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £45 /night

£314 - £643 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This mid 17th-century terraced holiday cottage offers spacious comfortable accommodation of a very good standard. It is ideal for a break at any time of year having a pleasant south facing garden and bright conservatory for the summer, and a cosy living room with a w...  …see more

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £41 /night

£286 - £636 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well-equipped holiday cottages (refs W43183, W43184 and W43185) stand in a landscaped courtyard, close to the own...  …see more

6 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £44 /night

£307 - £640 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Set on a quiet village lane, this semi-detached cottage with courtyard garden and small sun room provides very comfortable holiday accommodation. Set between Helmsley and Kirkbymoorside, both 3 miles, it is ideally placed to explore the North York Moors. Take a trip ...  …see more

9 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £44 /night

£307 - £560 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Peacefully located in this idyllic village, this holiday cottage dates back to the 1800s, 50 yards from Nunnington Hall. Ampleforth Abbey and college, 4 miles. Surrounded by country walks and excellent eating hostelries, the market towns of Helmsley, Easingwold and M...  …see more

6 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £43 /night

£295 - £680 / week

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Key info:

  • Not suitable for children
  • No pets allowed
In the North Yorkshire Moors National Park, this detached character holiday cottage sits peacefully in a picture postcard village, nestling in the unspoilt valley of the River Rye. Comfortable and well equipped with a secluded, enclosed sunny garden and superb views,...  …see more

8 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £44 /night

£303 - £608 / week

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Key info:

  • Not suitable for children
  • No pets allowed
This stone built former granary, attached to the owners' home, has been sympathetically converted to offer first floor holiday accommodation of a very good standard, within the stunning countryside of the Howardian Hills. A designated AONB, between the North York Moo...  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £97 /night

£674 - £1025 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Dating back to 1643 this former stone barn has been lovingly renovated by the present owners. Adjoining the original farmhouse, rustic features and exposed beams add to the holiday property's charm and character. Nestled peacefully on the moorside above the tiny haml...  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £47 /night

£327 - £893 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated in the picturesque market town of Helmsley, this imposing detached house with large gardens is comfortably furnished. An ideal holiday location for exploring coastal resorts such as Runswick Bay, Robin Hoods Bay and Whitby. Enjoy walks through the forests an...  …see more

12 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £43 /night

£298 - £804 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Situated on a working farm, this detached holiday cottage has far reaching countryside views over the Hovingham Estate in the Howardian Hills, an Area of Outstanding Natural Beauty. Enjoy dining alfresco on the patio area in the ¼-acre lawned garden, or relax beside ...  …see more

11 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £65 /night

£453 - £895 / week

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Key info:

  • Not suitable for children
  • No pets allowed
In the heart of the delightful market town of Helmsley, this cottage, one of a row, which originally formed part of the Duncombe Park Estate, has been lovingly renovated. Furnished to a high standard and full of character with exposed beams and stonework, and a south...  …see more

12 Photos

Cottage | 3 Bedrooms | sleeps 5

Very Good 4/5 

7 Nights min stay

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from £43 /night

£298 - £712 / week

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Key info:

  • Nearest beach 0 km
  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
This attractive Edwardian semi-detached house offers comfortable and spacious accommodation for up to five people.  …see more

7 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £62 /night

£428 - £892 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Pleasantly and peacefully situated, this beautiful property has been converted from a granary and boasts its own large, private walled garden. Set in the grounds of the owner's home, visitors enjoy shared use of a hard tennis court. Only a mile from the historic mark...  …see more

6 Photos

House | 1 Bedroom | sleeps 3

7 Nights min stay

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from £35 /night

£240 - £566 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Fully refurbished and with outstanding views over the Howardian Hills, in an AONB, this holiday cottage offers very comfortable accommodation for a couple at any time of the year. Situated on the edge of the National Park, there is excellent walking right from the do...  …see more

12 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £51 /night

£353 - £403 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Fox Cottage is situated just a short stroll from Helmsley's picturesque market square. Retaining its original character, this terraced holiday cottage features beamed ceilings, cruck beams and an open fire in a cast iron surround. Holidaymakers will enjoy the proximi...  …see more

14 Photos

Cottage | 2 Bedrooms | sleeps 4

Very Good 4/5 

7 Nights min stay

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from £51 /night

£352 - £738 / week

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Key info:

  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
This charming, sixteenth century thatched cottage includes two sitting rooms, two comfy bedrooms – one double and one twin, with limited head-room - and a stone flagged terrace.  …see more

19 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £56 /night

£387 - £848 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well equipped holiday cottages stand in a landscaped courtyard, close to the owners' farmhouse. Guests can enjoy ...  …see more

12 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £64 /night

£443 - £1115 / week

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Key info:

  • Not suitable for children
  • No pets allowed
With its own secluded garden leading down to the banks of the River Rye, this Grade II listed house is set just off the market square of the picturesque town of Helmsley. One of a pair, it is within easy walking distance of a selection of excellent shops, inns and re...  …see more

11 Photos

Cottage | 1 Bedroom | sleeps 2

Very Good 4.5/5 

7 Nights min stay

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from £36 /night

£249 - £465 / week

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Key info:

  • Not suitable for children
  • Car advised
  • No pets allowed
  • Private garden
As a one bedroom property, this lovely little cottage makes a great romantic getaway.  …see more

8 Photos

House | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £48 /night

£336 - £952 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Home Cottage is a Grade II listed Georgian house with its own enclosed cottage garden, with two sitting areas. Set in the heart of Hovingham, it is close to the village shop, two pubs with restaurants and two tea rooms. There is excellent walking in the Howardian Hil...  …see more

6 Photos

House | 1 Bedroom | sleeps 2

7 Nights min stay

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from £40 /night

£277 - £583 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Adjacent to the owners' home, this cosy, detached, single storey holiday cottage enjoys views across the Vale of York and a decked area which is perfect for alfresco dining. The village of Crayke, with an award-winning pub, provides an ideal base for exploring the ar...  …see more

9 Photos

House | 2 Bedrooms | sleeps 5

7 Nights min stay

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from £43 /night

£299 - £551 / week

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Key info:

  • Not suitable for children
  • No pets allowed
A charming 1700s property which has retained many original features, and is situated on the edge of the North York Moors National Park in a beautiful rural setting. The holiday cottage is full of character, with a cartwheel window in the former barn, open fireplace a...  …see more

16 Photos

House | 2 Bedrooms | sleeps 4

7 Nights min stay

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from £52 /night

£359 - £766 / week

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Key info:

  • Not suitable for children
  • No pets allowed
Within the North York Moors National Park, in a sheltered wooded valley close to the magnificent ruins of Rievaulx Abbey, these spacious, comfortable and well equipped holiday cottages stand in a landscaped courtyard, close to the owners' farmhouse. Guests can enjoy ...  …see more