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Helmsley Holiday Cottages

Helmsley Holiday Cottages

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    Helmsley Cottages

  • 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

    £138

    per night
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  • Last Minute Cottages - Pinfold Cottage
    • 1

    North Yorkshire

    Pinfold Cottage

    Ref: S121293

    Reviews 42

    3
    6
    With touches of elegance and style at every turn, Pinfold Cottage has been beautifully decorated and offers 5 star quality. This beautiful and luxurious newly built three bedroomed house is set in a secure and gated development in the historic...

    From

    £322

    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

    £145

    per night
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  • 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 - 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 - 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 - 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...

    From

    £296

    per night
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  • Last Minute Cottages - Castle View
    • 2

    North Yorkshire

    Castle View

    Ref: S3265

    Reviews 53

    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

    £300

    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

    £249

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

    North Yorkshire

    Linfitt - Helmsley

    Ref: S881439

    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 - Forge Cottage
    • 1

    North Yorkshire

    Forge Cottage

    Ref: S10818

    Reviews 15

    3
    6
    Forge Cottage is a charming stone-built detached property, situated in the beautiful market town of Helmsley, benefitting from a conservatory and a large enclosed garden with patio. Size: Sleeps up to 6, 3 bedrooms. Nearest beach: Less than 30...

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  • Last Minute Cottages - Orchard Cottage

    • North Yorkshire

    Orchard Cottage

    Ref: S84006

    2
    3
    Helmsley is a prestigious market town with a spacious market square surrounded by houses, hotels and shops. Helmsley has its own 12th century castle and English Heritage’s Rievaulx Abbey and Castle Howard are close by. Helmsley also boasts an arts...

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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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  • Last Minute Cottages - Mulberry Cottage

    • North Yorkshire

    Mulberry Cottage

    Ref: S364074

    Reviews 4

    3
    6
    High quality modern property in a gated courtyard, in the heart of the historic market town of Helmsley * Size:  3 bedrooms* Nearest pub: Less than 0.1 miles.* Nearest amenities: Less than 0.1 miles.* Short breaks: Available at this...

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  • Last Minute Cottages - Courtyard Cottage

    • North Yorkshire

    Courtyard Cottage

    Ref: S10889

    Reviews 5

    2
    5
    On the outskirts of the town of Helmsley is Courtyard Cottage a new building that is part of a quiet courtyard. There are interesting shops, restaurants and pubs in the market town and it is an ideal base for exploring the ancient city of York,...

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  • Last Minute Cottages - Osbourne Cottage

    • North Yorkshire

    Osbourne Cottage

    Ref: S84086

    4
    8
    Helmsley is a prestigious market town with a spacious market square surrounded by houses, hotels and shops. Helmsley has its own 12th century castle and English Heritage’s Rievaulx Abbey and Castle Howard are close by. Helmsley also boasts an arts...

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  • Last Minute Cottages - Coronation Cottage

    • North Yorkshire

    Coronation Cottage

    Ref: S260125

    At a Glance 2 bedrooms, 1 bathroom Dishwasher Garden / patio Pub / shop < 1 mile About this Holiday Cottage Coronation Cottage is a stone-built cottage tucked away in a central position in the market town of Helmsley, North Yorkshire. With...

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  • Last Minute Cottages - Little Manor Farm Cottage

    • North Yorkshire

    Little Manor Farm Cottage

    Ref: S248302

    1
    At a Glance 1 bedroom, 1 bathroom Garden / patio About this Holiday Cottage Situated just outside the pretty village of Nawton and a mere four miles from Kirkbymoorside and Helmsley is this delightful cottage - a cosy stone-built detached...

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  • Last Minute Cottages - Foxglove Cottage

    • North Yorkshire

    Foxglove Cottage

    Ref: S247759

    1
    At a Glance 1 bedroom, 1 bathroom Garden / patio Pub / shop < 1 mile About this Holiday Cottage Situated in the peaceful village of Harome and three miles from the market town of Helmsley is this charming, traditional cottage; a quaint,...

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  • Last Minute Cottages - Holly Cottage

    • North Yorkshire

    Holly Cottage

    Ref: S254151

    1
    At a Glance 2 bedrooms, 1 bathroom Garden / patio Pub / shop < 1 mile About this Holiday Cottage This 16th century thatched cottage in the picturesque rural village of Harome is a lovely example of such a property. Three miles from the market...

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  • Last Minute Cottages - Wethercote Cottage

    • North Yorkshire

    Wethercote Cottage

    Ref: S249590

    1
    At a Glance 2 bedrooms, 1 bath/ shower room 7 miles to Helmsley Great walking country About this Holiday Cottage Situated in a beautiful location in the North Yorkshire Moors National Park, Wethercote Cottage is surrounded by excellent...

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  • Last Minute Cottages - Ashberry Cottage

    • North Yorkshire

    Ashberry Cottage

    Ref: S264981

    About this Holiday Cottage An exceptionally pretty and romantic cottage (gable facing), peacefully set in a riverside location, just a mile walk from famous Rievaulx Abbey. With a cosy beamed interior, it offers an ideal location for exploring the...

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  • Last Minute Cottages - The Cottage

    • North Yorkshire

    The Cottage

    Ref: S260414

    1
    At a Glance 3 bedrooms, 1 bathroom Garden / patio Pub / shop < 1 mile About this Holiday Cottage The Cottage is an end-terraced stone cottage in the North Yorkshire village of Ampleforth. The cottage sleeps six people in three bedrooms - two...

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    Showing 1 - 24 of 52 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

    • Mr Foreman - Verified booking

      Pinfold Cottage is ideally located in the heart of Helmsley with all its attractions close to the door. We arrived in 3 cars and were initially concerned about parking but we found adequate spaces on Canons Garth Lane and Carlton Lane, in addition to the one allocated parking space in the courtyard. The Cottage is generally spacious, the only criticism being the ‘en-suite’ in one of the bedrooms which is very small. The downstairs toilet did become a substitute facility, especially when needing the use of a decent sized sink for shaving etc. The kitchen provides all the necessary requirements with a more than adequate quantity of cutlery, crockery and glasses. The property is warm with underfloor heating and the use of a wood burner in the lounge which we used as the outside temperature dropped to freezing. Two points to note 1) don’t follow the navigation instructions taking you up Elmslac Close at the side of the Black Swan, instead drive up Canons Garth Lane to the courtyard and 2) if using the back gate onto Elmslac Close to walk into town be careful of the 5 steps onto the lane. They weren’t well lit and a face plant was only just avoided. We had a great time and really enjoyed the Cottage.

      Read more less >

    • 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 >

    • Mr Chris Roche - Verified booking

      We have stayed in a fair few cottages over the years and though some were lovely many were extremely disappointing and a complete let down. Many have been period cottages but for some reason that resulted in quaint equals dingy and dirty, Pinfold cottage looked amazing on the website and the reality was a real treat. It was modern but cosy , clean and comfortable and had everything needed for a week away. Couldn’t fault it The cottage was situated in a great location too with everything a short walk away. Helmsley is la lovely town and obviously the area is beautiful We had a fantastic holiday and returning to Pinfold cottage after a days walking was a real luxury

      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 >

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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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