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Helmsley Holiday Cottages

Helmsley Holiday Cottages

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Did you know? We have a dedicated site just for pet friendly holidays, take me to Dog Friendly Cottages >

Helmsley Cottages

  • Last Minute Cottages - Bed in Nawton (93614)
  • 2

    York

    Bed in Nawton (93614)

    Ref: S810172

    2
    2
    Embrace a little bliss with your loved ones at this charming, traditional stone cottage hidden in the tranquil village of Nawton. Sleeping three people across two bedrooms, it s an ideal accommodation choice for couples or small families dreaming...

    From

    £85

    per night
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  • Last Minute Cottages - Bed in Helmsley (G0131)
  • 2

    North Yorkshire

    Bed in Helmsley (G0131)

    Ref: S228921

    2
    4
    converted church. Sleeping four guests and welcoming pups too, the two bedroom, Grade II listed abode is a sumptuous and unique place to base yourselves. Set just in beautiful gardens, just outside Helmsley and 25 miles from York, the property...

    From

    £115

    per night
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  • Last Minute Cottages - Foxglove Cottage
  • 1

    York

    Foxglove Cottage

    Ref: S376926

    Reviews 8

    1
    2
    Beadlam is a lovely village situated in the Ryedale district of North Yorkshire, resting on the edge of the North York Moors National Park, home to a farm shop and tea room, a local pub and a fish and chip shop. Helmsley market town is nearby...

    From

    £74

    per night
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  • Last Minute Cottages - Auburn House
  • York

    Auburn House

    Ref: S81850

    Reviews 66

    4
    8
    A village in the Ryedale district of North Yorkshire, Beadlam is directly joined onto another village, Nawton. The village offers a pub serving food and a local fish and chip shop. Nearby, about 3 miles away, is the market town of Helmsley,...

    From

    £93

    per night
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  • Last Minute Cottages - The Old Post Office
  • York

    The Old Post Office

    Ref: S591511

    Reviews 14

    5
    10
    The unspoiled village of Ampleforth, which is home to a few old homes, two pubs, a tearoom, and the neighbourhood store, is situated on the edge of the North York Moors National Park. There are several excellent restaurants nearby, and the market...

    From

    £126

    per night
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  • Last Minute Cottages - 29 Bondgate
  • 2

    York

    29 Bondgate

    Ref: S479191

    Reviews 32

    3
    6
    Helmsley is a prestigious market town in Upper Ryedale, on the southern edge of the North York Moors National Park. Helmsley has its own 12th century castle, and English Heritage's Rievaulx Abbey and Castle Howard are nearby. Helmsley also has an...

    From

    £82

    per night
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    LateRooms.com

  • Last Minute Cottages - Bellwether
  • North Yorkshire

    Bellwether

    Ref: S307894

    1
    2

    From

    £48

    per night
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    LateRooms.com

  • Last Minute Cottages - The Partridge
  • York

    The Partridge

    Ref: S936799

    2
    4

    From

    £210

    per night
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    LateRooms.com

  • Last Minute Cottages - Lawns Cottage
  • 3

    North Yorkshire

    Lawns Cottage

    Ref: S1023949

    2
    4

    From

    £64

    per night
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    LateRooms.com

  • Last Minute Cottages - 2 Bed in Helmsley G0131
  • 3

    York

    2 Bed in Helmsley G0131

    Ref: S959796

    2
    4

    From

    £131

    per night
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    LateRooms.com

  • Last Minute Cottages - Mill House
  • 3

    North Yorkshire

    Mill House

    Ref: S380754

    3
    5

    From

    £120

    per night
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    LateRooms.com

  • Last Minute Cottages - The Cart House
  • 3

    North Yorkshire

    The Cart House

    Ref: S417838

    3
    6

    From

    £149

    per night
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  • Last Minute Cottages - Beautiful North Yorkshire Stone Cottage
  • York

    Beautiful North Yorkshire Stone Cottage

    Ref: S988683

    3
    6

    From

    £157

    per night
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    LateRooms.com

  • Last Minute Cottages - The Pheasant
  • North Yorkshire

    The Pheasant

    Ref: S940772

    3
    6

    From

    £288

    per night
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    LateRooms.com

  • Last Minute Cottages - Auburn House
  • North Yorkshire

    Auburn House

    Ref: S292129

    4
    8

    From

    £108

    per night
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    LateRooms.com

  • Last Minute Cottages - The Old Post Office
  • York

    The Old Post Office

    Ref: S595801

    5
    10

    From

    £145

    per night
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  • Last Minute Cottages - Mason's Cottage
  • 3

    York

    Mason's Cottage

    Ref: S941702

    1
    2

    From

    £136

    per night
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  • Last Minute Cottages - Sunflower Cottage
  • York

    Sunflower Cottage

    Ref: S941262

    3
    6

    From

    £184

    per night
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    LateRooms.com

  • Last Minute Cottages - The Old Bank
  • 3

    York

    The Old Bank

    Ref: S942563

    5
    10

    From

    £402

    per night
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    LateRooms.com

  • Last Minute Cottages - Fairview
  • North Yorkshire

    Fairview

    Ref: S595126

    2
    3

    From

    £86

    per night
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    LateRooms.com

  • Last Minute Cottages - Fairview 2
  • York

    Fairview 2

    Ref: S980828

    1
    2

    From

    £86

    per night
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    LateRooms.com

  • Last Minute Cottages - Foxglove Cottage
  • York

    Foxglove Cottage

    Ref: S393626

    1
    2

    Check for price

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    LateRooms.com

  • Last Minute Cottages - Swiss Cottage
  • 3

    North Yorkshire

    Swiss Cottage

    Ref: S381868

    2
    4

    Check for price

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    LateRooms.com

  • Last Minute Cottages - Grange Cottage
  • North Yorkshire

    Grange Cottage

    Ref: S383532

    3
    6

    Check for price

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    Showing 1 - 24 of 31 properties

    Helmsley Holiday cottages

    Nestled in the heart of Ryedale, on the edge of the North Yorkshire Moors, is the pretty market town of Helmsley. A historic settlement with a Norman castle at its centre, Helmsley is well worth a visit for its medieval charm. Take a walk around the town walls, explore the local shops and stop for a bite to eat in one of the many quaint cafés.

    If you’re looking for somewhere to stay on your break, holiday cottages in Helmsley are the perfect option. With plenty of space for everyone, choose from large houses with private gardens, cosy cottages with open fires, or modern dwellings with stunning views.

    Holiday cottages in Helmsley can be booked through Snaptrip, with our best price guarantee ensuring you get the best deal on your break. With thousands of properties to choose from throughout the UK, we’ve got something to suit everyone. With our best price guarantee, you're sure to be getting the best deal on your holiday cottage. If you need a little extra hand finding the perfect holiday cottage, our friendly customer service team can help you find the perfect property - complete with hot tubs, private gardens and more.

    Other places to visit

    If you’re staying in Helmsley, why not explore some of these nearby towns and villages:

    Read more > less >

    Reviews

    What our customers say about their holidays

    • Janet - Verified booking

      We really enjoyed our stay at this wonderful, comfy and characterful cottage.

      it was spotlessly clean, excellently equipped and felt like a home from home. All the bedrooms were spacious and welcoming, and having the ground floor bedroom and adjacent shower room was ideal and much appreciated by our 80+ year old aunt. The location in a quiet village is great for local walks and relaxing and it made a great base to explore the North York Moors, local gardens and historic sites as well as bustling market towns. There's a pub and 2 eateries but no shop in the village, but there is a fantastic farm shop just 5 minutes drive away. Our only suggestions to make it even better are to provide a few more cereal and dessert bowls (we kept running out), and to provide some alternative lighter weight duvets or blankets as we were lucky enough to visit during the heatwave when 12tog duvets were far too hot! The listing could also be clearer about the patio and garden access. We enjoyed using the paved patio area up a few steps and OK for our elderly aunt to reach. But we were a bit disappointed that there is not yet any better access and no sitting area in the pretty side lawn - but appreciate that this may be to minimise any risk of disturbance to neighbours. Overall Auburn House is a delightful cottage that we'd happily recommend to others in search of a relaxing and cosy base for exploring wonderful North Yorkshire.

      Read more less >

    • Danielle - Verified booking

      Sykes Staff have been nothing but friendly and accommodating, they were not to fault for our unsatisfactory stay.

      The property however had dust webs left in corners (despite cleaners) and offered no QR code/Covid guidelines, no antibacterial hand wash or sanitiser (good job we took our own). We were greeted by a wasps nest by the front door obviously using the property’s roof. The door with its large double glass windows offered no privacy from passers by using the shared drive and communal laundry room given the fact the shower and toilet were right behind it which resulted in us having to hang a towel over the door. The pictures of the garden were misleading. It clearly shows a grass area which had been cordoned off and belonged to another property which only left the stoned area you see in the pictures which would have been fantastic if it weren’t for the fact they are not friendly to the paws of our fury friends which meant our pet friendly get away wasn’t in fact so pet friendly at all and his off lead play time went out the window. The directions to the property are not clear, even using ‘what four words’ we had difficulty. In the end we were forced to contact Sykes which then had to contact the owners who added another couple of steps to the directions. Frankly if it weren’t for the fact we had to rely on a family member for travel and our signal was so spotty we never would have stayed.

      Read more less >

    • Patricia - Verified booking

      The kitchen of Auburn House is well equipped.

      the house is clean but those are the only good points. Problems: The house is cold and it is impossible to heat it to a normal 20C as the thermostat, in a tiny, unlit passage has been set so that it goes off & returns to 9C after a short interval. There is a woodturner in the kitchen, 4 logs, 4 pieces of coal, firelighters & 3 pieces of kindling were supplied.3 uninsulated outer doors, one with gaps do not help. Sittingroom with gas fire but single glazed windows!. Dated decor, with old furniture (from sale room?) tarmac outside space, no usable garden for summer guests. General air of meaness & lack of welcome - lots of locked cupboards, information sheets telling guests not to put sticky hands on the sofas !No welcome pack. Warn winter guests to bring lots of logs, hot water bottles and winter clothes! This was by far the worst of Sykes properties that we have booked over the years. Auburn House - never again!

      Read more less >

    • Bart - Verified booking

      We really loved our stay in this little cottage, the cottage has been finished to a high level with comfortable furniture.

      It is in a great location to relax for a long weekend. We enjoyed dinner at the nearby Pheasant Hotel and walks along the river to Nunnington and chilled in the yard in front of the cottage. A couple of things that could be improved... the check-in and check-out times are not great, 6 pm check-in is very late. The dining table is not very usable and it would be great to be able to use some of the gardens of Holly Cottage as sitting in the sun on a bench is not the same as a bit of soft grass. But overall a great experience with some small improvements to make the stay even better.

      Read more less >

    • Ed - Verified booking

      We had a good time in the house.

      Two things only would have improved things. 1 Better signage to say Auburn House as photo view provided from side of house only visble looking back not forwards as went up road. As no number satnav unable to locate place accurately and bigger swinging sign in garden would have helped. It was only visible high up in brickwork! (2)The weather was cold at times and central heating only came on in middle of night or very late anyway, so needed better timings on it as these were locked away! Nevertheless, a really excellent place nice and clean that we hope to return to another time.

      Read more less >

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    Our cottages are professionally managed by our partners and payments are taken by them, but rest assured, by booking via Snaptrip you'll pay the lowest possible price for your trip.

    We never charge you more than you would pay booking directly on the partner's site and if you become a member you can save even more. If you find a property priced lower anywhere else on the internet (we’d be amazed if you do), simply email us at marketing@snaptrip.com and we'll refund you the difference.

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    Things to do near Helmsley

    • Activity Activity

    Mathewsons Classic Cars

    Mathewsons is a family run classic car, motorbike and memorabilia auction house based at Roxby Garage, Thornton Le Dale. It was brought to light by the TV series Bangers & Cash which follows the Mathewsons family Derek, Paul and Dave, plus their team running the auction business. . Gift Shop and ability to view auction lots.

    Rievaulx Abbey

    Iconic English abbey ruins in the North York Moors - explore the history of the mediaeval monks at Rievaulx Abbey with onsite cafe, exhibition and tours.

    Flamingo Land

    Flamingo Land in North Yorkshire is a thrilling theme park and zoo, offering an action-packed day out for all ages. With over 100 rides and attractions, including roller coasters, water rides and a zoo with over 140 species, it’s a must-visit destination. The park also offers accommodation, making it perfect for a weekend getaway. Address: Kirby Misperton, Malton, North Yorkshire YO17 6UX

    World of James Herriot

    Family friendly 1950's themed farm with activities including trying your hand in the TV studios and test the variety of vets equipment. Gift shop, toilets.

    Nunnington Hall

    Elegant 17th century manor house from the stylish oak-panelled hall to the haunted room and attics. Free parking, pet friendly, groups welcome, National Trust.

    Eden Camp Modern History Theme Museum

    A true WW2 experience for those who want to immerse themselves in the sights and sounds of the war in a former World War 2 Prisoner of War Camp. Dog friendly - well behaved dogs on a lead are allowed. Family friendly.

    Ryedale Folk Museum

    A great North Yorkshire family day out where you can explore the history and the traditions of the area from an Iron Age hut to a 1950s village shop.

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