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Helmsley Holiday Cottages

Helmsley Holiday Cottages

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    Helmsley Cottages

  • Last Minute Cottages - 3 Bed Cottage in Helmsley

    • North Yorkshire

    3 Bed Cottage in Helmsley

    Ref: S230806

    3
    6
    Additional information and rules No dogs allowed - 3 bedrooms - 1 super-king-size (can also be made up as a twin on request), 1 double and 1 twin - 3 bathrooms - 2 en-suite shower rooms with WC, 1 bathroom with Jacuzzi bath, plus 1 additional...

    From

    £227

    per night
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  • Last Minute Cottages - 2 Bed Cottage in Helmsley
    • 2

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S228921

    2
    4
    Additional information and rules - 2 bedrooms – 1 king-size and1 double sofa bed in the second lounge - 1 bathroom with shower over bath and WC - 1 wet room - Kitchen with oven, hob, dishwasher, washer/dryer, microwave and fridge with small...

    From

    £127

    per night
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  • Last Minute Cottages - 2 Bed Cottage in Helmsley
    • 1

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S230564

    2
    3
    Additional information and rules - 2 bedrooms: 1 king-size bed, 1 single bedroom - 1 bathroom: wet room with walk-in shower and WC - Semi-detached property - Wood burner - Heated flooring - Welcome hamper upon arrival - Oven and hob,...

    From

    £127

    per night
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  • Last Minute Cottages - Cherry Tree House
    • 2

    North Yorkshire

    Cherry Tree House

    Ref: S84814

    Reviews 57

    4
    8
    Cherry Tree House is a beautiful luxury property near the centre of Helmsley. With stunning contemporary kitchen diner, quirky garden room, four double bedrooms and a garden with patio and outside seating, it is an ideal place for families and...

    From

    £204

    per night
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  • Last Minute Cottages - 2 Bed Cottage in Helmsley
    • 2

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S777440

    2
    4
    Additional information and rules - 2 bedrooms - 1 king-size, 1 twin (400TC Egyptian cotton) - 3 bathrooms - 1 en-suite with shower and WC, 1 en-suite with shower over bath and WC, 1 downstairs walk-in shower and WC - Electric range cooker with...

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

    North Yorkshire

    3 Bed Cottage in Helmsley

    Ref: S366423

    3
    4
    Additional information and rules - Sleeps 4 + 1 - 3 bedrooms – 1 double, 1 twin and 1 single - 1 shower room with shower and WC - Electric range-style oven and gas hob, microwave, fridge/freezer and dishwasher, please note there is no washing...

    From

    £117

    per night
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  • Last Minute Cottages - Castle View
    • 2

    North Yorkshire

    Castle View

    Ref: S3265

    Reviews 55

    4
    8
    On the southern edge of the North York Moors National Park is the prestigious market town of Helmsley. Lying in a sheltered corner of Upper Ryedale, this lovely settlement boasts a spacious market square surrounded by houses, hotels and shops as...

    From

    £254

    per night
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  • Last Minute Cottages - Cygnet Cottage

    • North Yorkshire

    Cygnet Cottage

    Ref: S479622

    Reviews 22

    3
    6
    Bright and fresh, three bedroom quality modern property, sleeping six, in a gated courtyard, in the heart of the historic market town of Helmsley * Size: Sleeps 6, 3 bedrooms* Nearest pub: Less than 0.2 miles.* Nearest amenities: Less than 0.2...

    From

    £161

    per night
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  • Last Minute Cottages - Linfitt - Helmsley
    • 2

    North Yorkshire

    Linfitt - Helmsley

    Ref: S881439

    Reviews 1

    4
    8
    Escape to this beautiful holiday home set in one of North Yorkshire’s prettiest towns, Helmsley, in the North York Moors National Park. Voted one of the best places to live in the UK in a Sunday Times survey, picture-postcard Helmsley offers a...

    From

    £283

    per night
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  • Last Minute Cottages - Fox Cottage
    • 2

    North Yorkshire

    Fox Cottage

    Ref: S1028684

    2
    4
    Fox Cottage is a dog-friendly holiday cottage sleeping up to four guests in the North Yorkshire market town of Helmsley with a good choice of amenities including eating establishments on the doorstep. Undergoing substantial refurbishment in early...

    From

    £114

    per night
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  • Last Minute Cottages - Ivy Cottage

    • North Yorkshire

    Ivy Cottage

    Ref: S75218

    Reviews 35

    3
    5
    Situated on the southern edge of the North York Moors National Park, Helmsley is a prestigious market town with a spacious market square surrounded by houses, hotels and shops. There is excellent walking on the doorstep, the Cleveland Way starts...

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    Partner deal

  • Last Minute Cottages - The Byre
    • 3

    North Yorkshire

    The Byre

    Ref: S1003993

    1
    2

    From

    £88

    per night
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    Partner deal

  • Last Minute Cottages - The Nest
    • 3

    North Yorkshire

    The Nest

    Ref: S601027

    1
    2

    From

    £54

    per night
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    Partner deal

  • Last Minute Cottages - The Old Back Kitchen At Bonfield Ghyll Farm
    • 3

    North Yorkshire

    The Old Back Kitchen At Bonfield Ghyll Farm

    Ref: S518997

    1
    2

    From

    £117

    per night
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    Partner deal

  • Last Minute Cottages - Bridge House

    • North Yorkshire

    Bridge House

    Ref: S377695

    2
    4

    From

    £67

    per night
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    Partner deal

  • Last Minute Cottages - The Annex - central Helmsley with parking
    • 3

    North Yorkshire

    The Annex - central Helmsley with parking

    Ref: S523226

    2
    4

    From

    £194

    per night
    View
    Partner deal

  • Last Minute Cottages - Rye Cottage
    • 3

    North Yorkshire

    Rye Cottage

    Ref: S381346

    3
    6

    From

    £164

    per night
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    Partner deal

  • Last Minute Cottages - The Old Post Office - Central Helmsley with Parking

    • North Yorkshire

    The Old Post Office - Central Helmsley with Parking

    Ref: S519372

    2
    6

    From

    £179

    per night
    View
    Partner deal

  • Last Minute Cottages - The Pheasant

    • North Yorkshire

    The Pheasant

    Ref: S940772

    3
    6

    From

    £288

    per night
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    Partner deal

  • Last Minute Cottages - Holly-Garth
    • 3

    North Yorkshire

    Holly-Garth

    Ref: S1016725

    4
    8

    From

    £265

    per night
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    Partner deal

  • Last Minute Cottages - Rye Court Cottage and Annex Central Hemsley
    • 3

    North Yorkshire

    Rye Court Cottage and Annex Central Hemsley

    Ref: S524778

    5
    13

    From

    £532

    per night
    View
    Partner deal

  • Last Minute Cottages - Bilsdale Cottage
    • 3

    North Yorkshire

    Bilsdale Cottage

    Ref: S323151

    2
    4

    Check for price

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    Partner deal

  • Last Minute Cottages - Rosebeck
    • 3

    North Yorkshire

    Rosebeck

    Ref: S1013079

    2
    4

    Check for price

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    Partner deal

  • Last Minute Cottages - Toad Hall

    • North Yorkshire

    Toad Hall

    Ref: S385511

    2
    4

    Check for price

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    Showing 1 - 24 of 28 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

    • Mrs Cross - Verified booking

      The key safe system worked perfectly and the owner stopped by to advise on lighting and with recommendations in Helmsley. The house is large with plenty of room to accommodate 8 people and you wouldn't need to meet each other during the week!. It is a lovely quirky house which instantly feels like home. The beds are comfy and the shower works excellent with good water pressure. Parking was good at the back of the house and most days there was parking at the front too. Its a 5 minute walk into Helmsley and my 82 year old parents with hip and knee issues both found it easily walkable. The owner, who lives next door, popped in most days to ask how things were going despite giving his number out to contact him if there were issues. A fantastic stay in a great house !

      Read more less >

    • Mr Knox - Verified booking

      Cherry Tree house is in a great location just a ten minute walk from the centre of picturesque Helmsley. The owner is onsite and popped in regularly with items we felt should have been there when we arrived. There is no welcome pack which would have been nice if only with some essentials in. The house is in need of some maintenance especially outside and upstairs as it is very tired and a lot of things didn’t work. We thought this house would suit a family with children better than a group of mature adults who want a bit more luxury accommodation. On the plus side the beds were very comfortable, lovely quality bed linen and bedding and the house was clean. The kitchen was a good size for a group and was adequately equipped.

      Read more less >

    • Stephen - Verified booking

      A totally stunning cottage in the most beautiful village location within walking distance of all the local amenities .

      We had a wonderful holiday and had the most amazing weather, we LOVED the outdoor village swimming pool!! Helmsley is lucky to have such a wonderful asset. The cottage has everything you could possibly need and suited out needs perfectly as the ground floor bedroom and shower room was ideal for elderly parents. The cottage was spotlessly clean, very well equipped and felt very homely. The lovely garden was great for a family bbq and we enjoyed looking out on to it from the fantastic conservatory. We will definitely return to this property as we had such a lovely time exploring North Yorkshire. Thank you for everything, we can tell a lot of thought, care and attention has gone into this holiday home.

      Read more less >

    • Miss Andrea Sellas - Verified booking

      The property was absolutely stunning. We were a party of 8 and spent the New Year in at Cherry Tree House. It was perfect. We had a fabulous dinner party in the gorgeous kitchen on NYE and then went into the lounge and played party games and then let the New Year in. Everything was done to a high specification even down to the crockery and kitchen utensils. Harry the owner is a great guy. I would definitely recommend you try this property. You won't be disappointed. We will be back. Helmsley is also such a lovely town. Handy for country walks with the dog and also not too far for a trip to the coast.

      Read more less >

    • Mr Martin Powell - Verified booking

      The house is equipped with lovely quirky old fittings, and family heirloom pieces of furniture, as well as brand new kitchen equipment, TVs etc, and is both comfortable and spacious. The friendly owner lives in an adjacent property, and was helpful when needed, but not intrusive. Helmsley has all the amenities needed in a picturesque setting, including its own castle, walled gardens, and nature reserve while being perfectly located for exploring the Moors, coast and York, plus within a decent walk of Rievaulx Abbey. We had a great time, and would definitely recommend this property.

      Read more less >

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    Best price guarantee

    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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