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Family-friendly holiday rentals in Helmsley

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Quick stats about holiday rentals that are family-friendly in Helmsley

  • Total holiday rentals

    Explore 40 holiday rentals in Helmsley

  • Nightly prices starting at

    Helmsley holiday rentals start at $288 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,610 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Helmsley holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Helmsley rentals

  • 4.8 Average rating

    Helmsley stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated family-friendly rentals in Helmsley

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A living area is depicted featuring a plush red sofa adorned with floral cushions. A rustic wooden coffee table centers the room, while a potted plant adds a touch of greenery. Light streams in through a large window, with a staircase visible in the background.
Home in Helmsley

Central Fully Ensuite house sleeps 6 dog friendly

The house is in the Centre of Helmsley but located in a very quiet area with great views, close to the shops, galleries, restaurants and Duncombe Park. It is a lovely spacious house, that has 3 ensuite bathrooms and therefore is great for couples, families and small groups. It is ideal for exploring North Yorkshire. The adjacent property, 2 Stonegarth can be let with this property. It is ideal for two families that want privacy but can come together for meals etc. Well behaved dogs allowed.

4.98 out of 5 average rating, 118 reviews
Top Guest favourite
A stone cottage exterior is highlighted, featuring a white door and window. Pink flowering shrubs adorn the entrance. A wooden table with chairs is arranged on a stone patio, surrounded by a green fence and under a partly cloudy blue sky.
Apartment in Gilling East

Fairfax View - delightful annexe cottage, Gilling

Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

4.97 out of 5 average rating, 213 reviews
Top Guest favourite
A cozy suite is featured, with a spacious bed neatly made. A comfortable seating area contains a gray sofa with decorative pillows, a vintage trunk, and a piano. Natural light pours through two windows, illuminating the wooden floor and soft wall colors.
Guest suite in Nunnington

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

4.88 out of 5 average rating, 225 reviews
Guest favourite
The stone cottage exterior features a traditional design with a red-tiled roof and green door. Lush climbing plants adorn the front, complementing the nearby window boxes. The surrounding lawn is neatly maintained, enhancing the welcoming appearance of the cottage.
Cottage in Helmsley

Pretty Yorkshire Stone Cottage Harome

A charming stone cottage situated in the picturesque village of Harome, 3 miles from the market town of Helmsley.This characterful cottage is up to date with everything you need without losing original features of beamed ceilings & a cosy log burner. The cottage offers luxe accommodation with a spacious kitchen, two delightful bedrooms, a power shower, bath, well equipped kitchen & hotel grade linen. A cosy sitting room with open plan dining area. There is a little garden outside with a table.

4.94 out of 5 average rating, 104 reviews
Top Guest favourite
Home in North Yorkshire

Gorgeous country cottage, Nawton near Helmsley

A beautifully converted, luxury 3 bedroomed country cottage in a stunning village setting. Stunning Dark Skies of the North Yorkshire National Park AONB and all within easy reach of the the gorgeous East coast towns and beaches. A few minutes drive to the beautiful market town of Helmsley and Malton, with all amenitites, cafes/restaurants. Michelin starred restaurants The Pheasant, The Star, The Black Swan and Restaurant Myse are a few minutes drive away and The Yorkshire Spa Retreat.

4.98 out of 5 average rating, 232 reviews
Top Guest favourite
The three-storey town house features a classic stone facade with large windows that allow natural light to fill the interior. The entrance includes two white doors, each framed by decorative columns, with a small set of steps leading up to them.
Home in Kirkbymoorside

The Town House

This family and dog friendly three storey town house in the centre of Kirkbymoorside gives easy access to shops, pubs, the local market and childrens play area, and a 1 minute walk finds you in open fields with public footpaths. Stroll around the outskirts of town or head off on foot to explore the moors, woodlands and villages. The coast, Dalby and Cropton forest, North York Moors National Park, Pickering steam railway, Flamingoland, Malton and the city of York are in easy driving distance.

4.93 out of 5 average rating, 102 reviews
Guest favourite
An outdoor seating area is showcased, featuring two wicker chairs and a small table, situated on a stone patio. Surrounding flowers in bloom add color to the space. The rustic stone cottage stands in the background, complemented by a clear blue sky above.
Cottage in Laskill

Rievaulx is a delightful one-bedroom cottage with kitchen and lounge.

Rievaulx is a delightful one-bedroom cottage with your own kitchen, lounge, and bathroom. We stand proudly in beautiful Bilsdale, six miles north of Helmsley, in the stunning North Yorkshire Moors National Park. It is surrounded by hills and open countryside which fringe the unique open moors. Traditionally built of Yorkshire stone in the seventies Laskill has its own private spring water supply that runs down from the hillside - definitely worth a sample.

4.82 out of 5 average rating, 105 reviews
Guest favourite
A cozy living room features a light wooden floor and a plush red area rug. A comfortable sofa is complemented by an armchair, with a coffee table positioned centrally. Artwork adorns the walls, and a modern fireplace sits at one corner. Natural light brightens the space.
Cottage in Helmsley

Cliff Stud Retreat, Helmsley - Cecil Cottage

Book Direct - 15% saving - Cliff Stud Retreat Cecil cottage is a 3 bed cottage set on a horse stud farm surrounded by 220 acres with stunning countryside views you’re sure to feel relaxed from the minute you arrive. Cecil cottage sleeps up to 5 guests and has a fully equipped kitchen, modern bathroom which has a shower/bath located downstairs. There is also a wood burner and an enclosed garden. The cottage is close to the centre of Helmsley, 5 min drive.

4.86 out of 5 average rating, 154 reviews
Top Guest favourite
Multiple paned windows frame a pleasant view of greenery and colorful trees outside. A decorative bowl and two ceramic jugs rest on the windowsill, allowing natural light to fill the space.
Apartment in Helmsley

The Flat @ 2 Castlegate

Situated right in the heart of the market town of Helmsley, this flat boasts views of Helmsley Castle, just a stone's throw from the rear of the garden. A perfect hub for those wanting to soak up some Yorkshire scenery with the home comforts of local conveniences. Helmsley has been noted as a major food destination with excellent cafés and highly acclaimed restaurants in the town and three Michelin starred restaurants a short drive away.

4.98 out of 5 average rating, 229 reviews
Top Guest favourite
A charming cabin is shown with a unique curved design, featuring two open doors that invite entry. The exterior is made of wood and is set against a backdrop of lush greenery and blooming bushes. A picnic bench and flat seating area are visible in the foreground.
Cabin in North Yorkshire

Cosy Rural Cabin with Private Hot Tub

Water Hall Farm by Wigwam Holidays is part of the UK's No1 glamping brand that has been providing guests with 'great holidays in the great outdoors' for over 20 years! Our site has 6 ensuite cabins with private hot tubs. Water Hall Farm by Wigwam Holidays is tucked away on the edge of the North Yorkshire Moors. Surrounded by beautiful countryside, there’s always something to do on this bustling working farm.

4.91 out of 5 average rating, 398 reviews
Guest favourite
A comfortable living room features a brown sofa and an armchair, positioned on a light brown area rug. A flat-screen TV is mounted on the wall above a decorative media console. Natural light enters through two large windows, adorned with patterned curtains.
Cottage in Helmsley

Clothes Prop Cottage, a Helmsley hideaway

Clothes Prop Cottage is located in the heart of Helmsley, just a couple of minutes walk from the shops, tea rooms, pubs and restaurants in this beautiful North Yorkshire market town. The property is available for 3 night weekend and 4 night mid week stays as well as full 7 night breaks. The property suits couples looking for a relaxing stay in the Yorkshire countryside, with their beloved pets welcome!

4.93 out of 5 average rating, 316 reviews
Top Guest favourite
A warm sitting area features two plush, teal armchairs and a comfortable sofa with vibrant cushions. Natural light streams through multiple windows, accentuating the wooden interior. Deep floral drapes frame the views, inviting a sense of tranquility within the cozy space.
Place to stay in North Yorkshire

Boutique log cabin with spectacular moorland views

Commanding panoramic views over Newton Dale and the North York Moors Steam Railway, High Kingthorpe Lodge is a boutique-style holiday retreat set in two and a half acres of private woodland. This lovely lodge and its stunning location are a haven of comfort and tranquility and yet only a short trip away from some of North Yorkshire's most popular attractions.

4.98 out of 5 average rating, 184 reviews

Popular amenities for Helmsley family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
The exterior of the property is shown, featuring a charming facade with a tiled roof. A patio area includes seating arrangements surrounded by lush greenery, offering a cozy space for relaxation. Large windows allow for ample natural light, enhancing the inviting atmosphere.
Home in Shipton

The Stables with Jacuzzi & tennis court

4.95 out of 5 average rating, 317 reviews
Top Guest favourite
A historic building is set against a backdrop of blue sky, with seasonal flowers blooming in the foreground. Crocuses and small yellow flowers create a vibrant carpet of color across the lush, green lawn, inviting relaxation and appreciation of the natural surroundings.
Home in Langton

North Wing of Langton Hall - Grade 2 listed

4.94 out of 5 average rating, 197 reviews
Top Guest favourite
Tiny home in North Yorkshire

Magical A-Frame Wooden Cabin Nestled in Woodland

4.97 out of 5 average rating, 118 reviews
Top Guest favourite
A stone cottage with a red-tiled roof is visible behind a dry-stone wall. Brightly colored flowers and greenery surround a playful pig statue in the foreground. The sunny sky provides a clear view of the welcoming farmhouse and its charming surroundings.
Cottage in Newton-on-Rawcliffe

Charming farm based cottage with hot tub/sauna

4.98 out of 5 average rating, 232 reviews
Top Guest favourite
A woodfired hot tub is set in a private outdoor area, surrounded by warm lighting and a rustic wooden structure. The evening sky deepens to twilight, enhancing the tranquil ambiance. Logs are neatly arranged nearby, providing easy access for fueling the hot tub.
Farm stay in Pockley

Couple's Bothy near Helmsley in the National Park

4.97 out of 5 average rating, 237 reviews
Top Guest favourite
A large tree trunk is visible in the foreground, with a bud on a branch. In the background, a wooden structure resembling a cabin is surrounded by a grassy field, fenced areas, and greenery, set against an overcast sky.
Cabin in Low Dalby

Dalby Forest Luxury Lodge

4.98 out of 5 average rating, 120 reviews
Guest favourite
An aerial view captures the cabin surrounded by lush greenery and open fields. The setting sun casts a warm light over the landscape, highlighting the peaceful atmosphere. A wooden hot tub is visible nearby, nestled among the trees, with picturesque countryside views extending beyond.
Farm stay in York

Farm Glamping Cabin with Hot Tub - amazing views.

4.77 out of 5 average rating, 503 reviews
Top Guest favourite
A wooden lodge is nestled within lush green woodland, surrounded by trees. The structure features a spacious deck with outdoor seating, and a Scandinavian style wood-fired hot tub is situated nearby, blending seamlessly into the natural setting.
Cabin in Rivendell

2 bedroom lodge with hot tub in private woodland

4.94 out of 5 average rating, 168 reviews

Family- and pet-friendly home rentals

Guest favourite
A bright bedroom features a spacious bed with soft bedding, complemented by a decorative chest of drawers. Natural light floods the room, highlighting the neutral decor. A doorway leads to an en-suite bathroom, and a comfortable seating area is visible in the background.
Home in Kirkbymoorside

Oakforge Cottage, a spacious home from home.w

4.9 out of 5 average rating, 476 reviews
Top Guest favourite
Place to stay in Urra

Maltkiln House Annexe North Yorkshire moors

4.98 out of 5 average rating, 283 reviews
Top Guest favourite
The open-plan space features a spacious bed with plush bedding and two leather armchairs positioned beside a wooden dining table. Natural light enters through a window with checked curtains, creating a cozy ambiance. A flat-screen TV is mounted on the wall nearby.
Guesthouse in Kilburn

The Little House Peaceful & self-contained

4.99 out of 5 average rating, 206 reviews
Guest favourite
A large floor-to-ceiling window offers expansive views of the countryside and sunlight filtering through trees. A warm wooden bench is adorned with a welcoming sign and small plants. A cozy coffee table with decorative items can be seen in front, enhancing the inviting space.
Barn in Aislaby

Stunning views, 4 acres, dog friendly, Yorkshire

4.94 out of 5 average rating, 382 reviews
Top Guest favourite
The exterior of a charming stone cottage is displayed, featuring a distinctive red pitched roof. Flower pots with blooming plants adorn the entrance. A well-maintained gravel pathway leads to the door, surrounded by lush greenery and shrubbery.
Home in Ampleforth

Little Hillside

4.97 out of 5 average rating, 145 reviews
Guest favourite
A cozy bedroom features a king-size bed dressed in a floral-patterned blanket. Soft lighting from the window enhances the calm atmosphere, with two bedside tables and lamps on either side. Wall art and a radiator add character to the space, complemented by neutral tones.
Guest suite in Ampleforth

Lovely self-contained hillside village Annexe

4.91 out of 5 average rating, 312 reviews
Top Guest favourite
The exterior of the cottage showcases a charming stone facade with a red-tiled roof. A staircase leads to the entrance, and a large parasol shades a wooden table and chairs on a gravel patio. Lush greenery and trees surround the property.
Cottage in East End

The Owlets, Ampleforth

4.98 out of 5 average rating, 348 reviews
Top Guest favourite
The exterior of the cottage displays a charming stone facade with a red-tiled roof. A large window with multiple panes is positioned at the front, while two dormer windows are set into the roof, providing additional natural light to the upper levels.
Cottage in North Yorkshire

Castlegate Cottage

4.93 out of 5 average rating, 417 reviews

Family-friendly home rentals with a pool

Guest favourite
A heated indoor swimming pool is seen, featuring clear water reflecting natural light. Large windows provide views of the surrounding garden. A pink float is positioned in the water, adding a touch of color to the serene setting.
Bungalow in York

Ellerburn Lodge

4.88 out of 5 average rating, 241 reviews
Top Guest favourite
An aerial view captures the rustic cabin surrounded by expansive green fields, with rolling hills visible in the background. The property features a red-tiled roof and a spacious gravel area for parking. Fencing encloses the garden, offering a sense of privacy and openness.
Farm stay in Broxa

The View Broxa - Luxury Lodge - Yorkshire Coast

4.99 out of 5 average rating, 187 reviews
Guest favourite
A cozy lounge area is furnished with a blend of comfortable seating, including a tufted blue sofa and a brown leather couch. A small wooden table displays a tea set, while a chessboard is ready for play. Natural light filters through a large window, offering a view of greenery.
Home in North Yorkshire

Cosy 2 bedroom river/coastal retreat. Heated pool.

4.81 out of 5 average rating, 132 reviews
Top Guest favourite
A light blue beach house is featured, set against a clear blue sky. A spacious deck is adorned with a white umbrella, while a comfortable seating area invites relaxation. Lush green grass surrounds the property, contributing to a cheerful outdoor setting.
Cabin in Filey

Secret of Eden Beach House - Pet friendly WiFi E.V

4.97 out of 5 average rating, 442 reviews
Top Guest favourite
A wooden table set with plates and glasses is positioned beside the outdoor seating area. Two stylish chairs are placed nearby, and the inviting entrance of the tree cabin is visible in the background, surrounded by lush greenery and the tranquil mill pond.
Treehouse in West Yorkshire

The Tree Cabin

4.99 out of 5 average rating, 352 reviews
Top Guest favourite
The exterior of a two-story brick cottage is presented, showcasing a modern architecture with white window trims. A well-maintained lawn and hedges frame the property, while a clear blue sky with scattered clouds provides a bright backdrop.
Cottage in Filey

Willow Cottage: 3 Bed, 3 Bath, Pool, WiFi, dogs

4.97 out of 5 average rating, 132 reviews
Guest favourite
A balcony railing offers a clear view of the expansive green landscape that leads to the sea. Gentle slopes and distant coastline are visible under a bright blue sky, creating a serene outdoor atmosphere.
Cottage in North Yorkshire

3 bedroom cottage with fabulous sea views.

4.85 out of 5 average rating, 102 reviews
Top Guest favourite
The exterior of a modern cabin is surrounded by a gravel terrace, featuring two black chairs and a table. A hot tub is positioned nearby. Large glass sliding doors invite natural light into the interior while showcasing views of the surrounding landscape.
Cabin in Ferryhill

Luxury Cabin with Hot Tub & Spa Facilities

4.97 out of 5 average rating, 120 reviews

Destinations to explore