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Cottage vacation rentals in Helmsley

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Quick stats about cottage rentals in Helmsley

  • Total vacation rentals

    Explore 30 vacation rentals in Helmsley

  • Nightly prices starting at

    Helmsley vacation rentals start at ﺩ.ﺇ 624 per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Helmsley vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Helmsley rentals

  • 4.7 Average rating

    Helmsley stays receive an average rating of 4.7 out of 5 from guests

Top-rated cottage rentals in Helmsley

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite
The stone cottage exterior showcases charming details, including a wooden door painted in soft blue. Flower pots filled with pink and white blooms adorn the entrance, enhancing the inviting appeal of the home. A small window is framed by additional greenery.
Cottage in Castleton

Cheerful & Quaint 18th Century cottage

Pretty cottage situated on the village green in the heart of Castleton village. Open fire for creating a cosy night in & perfect for exploring the beautiful North Yorkshire Moors. Castleton is lucky to have two great pubs The Downe Arms with fabulous food and atmosphere right across the road and The Eskdale which serves lovely ‘fine dining food’ but also lovely just for a drink. There’s the Old Chapel Tearoom, a Londis & ‘Off the Scale’ shop We are also along the Esk Valley train line to Whitby

FamilyLocationPets

4.96 out of 5 average rating, 293 reviews
Top guest favorite
The exterior of a stone cottage is viewed, featuring a gabled roof and white window frames. A gravel parking area is present in front, with green hedges lining one side. A wooden door offers entrance, and a farm structure is partially visible to the left.
Cottage in Cawton

The Cake House

The Cake House is a cosy 3 bedroom country cottage situated in the picturesque village of Cawton, North Yorkshire. Perfect holiday location for stunning, rural walks, situated just a stones throw from The Ebor Way. Enjoy pub lunches and beautiful places to explore. York city Center- is a 30 min drive. Historic, market town Helmsley is 7 miles away, full of cosy coffee shops/ pubs/ restaurants and shops. Villages Hovingham and Gilling East (2-3 mile walk) both have great pubs and playgrounds

LocationFamilySleep quality

4.96 out of 5 average rating, 190 reviews
Top guest favorite
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

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

FamilyValuePets

4.98 out of 5 average rating, 348 reviews
Guest favorite
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.

FamilyLocationLaundry

4.94 out of 5 average rating, 104 reviews
Top guest favorite
The exterior of a charming stone cottage is visible, featuring a traditional roof with red tiles. Two entrances can be seen, framed by multiple windows that allow natural light to enter. The facade combines a rustic aesthetic with neighborhood characteristics.
Cottage in North Yorkshire

Lovely cottage for N. York Moors & Steam Trains

19 Burgate is in the popular market town of Pickering, minutes’ walk from shops, eating places, Castle & Steam Railway (seasonal) - ideal for exploring the Moors, coastline & historic sights. It offers contemporary comfort, with a cosy living room, modern kitchen-diner, luxurious bathroom (walk-in shower, bath) & quality bedrooms. The garden offers eating/drinks outside and access to private parking. Prices are for 2 guests, with a small extra charge for the 2nd bedroom and well-behaved pets.

ValueLocationTV

4.94 out of 5 average rating, 163 reviews
Top guest favorite
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

Located on a farm just outside of the market Town of Pickering, Swallow Cottage is a charming, pet friendly 3 bedroom cottage, complete with hot tub, sauna and games room. We’re well placed for visits to the stunning yorkshire coast, and have plenty of excellent walking and biking routes on the doorstep. Key features of the cottage include •hot tub •sauna •games room including pool table •farm setting •local pub within walking distance •3 en-suite bedrooms •pet friendly •WiFi and smart tv

LocationValueSleep quality

4.98 out of 5 average rating, 232 reviews
Top guest favorite
The charming brick cottage features a traditional red-tiled roof and white-framed windows. Lush greenery surrounds the property, with a small garden area visible in the foreground. A wooden gate leads to the entrance, giving a sense of privacy in this tranquil setting.
Cottage in Sessay

The Cobbler's Cottage

Nestled in the scenic North Yorkshire village of Sessay, this charming former cobbler's cottage offers a spacious retreat. Inside, you'll find a wood-burning stove, TV, Blu-ray player, and a modern kitchen equipped with an oven, microwave, dishwasher, fridge freezer, Nespresso coffee maker, and a washing machine. Step outside to a private patio complete with a dining area and barbecue. Plus, we warmly welcome one well-behaved pet, so you can bring your furry friend along if you desire.

FamilyValueHeating

4.96 out of 5 average rating, 376 reviews
Top guest favorite
Cottage in Brandsby

Seaves Mill luxury cottage Brandsby north of York.

Seaves Mill situated on the edge of The Howardian Hills in the North Yorkshire village of Brandsby 13.5 miles from the city of York. Seaves Mill has been converted into this beautiful living space by avid gardeners and architectural antique dealers Phil and Jo. The space has been designed with quality and decorative design in mind. It is set within beautifully landscaped gardens along side the picturesque Mill stream. Described by guests as "more of an experience than just a stay."

ValueLocationCondition

4.99 out of 5 average rating, 118 reviews
Top guest favorite
A scenic view of a cottage by the River Seven is presented, with a backdrop of lush greenery and blooming daffodils adorning the riverbank. The charming stone building features a red-tiled roof and multiple windows reflecting the serene countryside.
Cottage in Sinnington

Goose End Cottage, North Yorkshire

Take a break and unwind in a characterful cottage set in beautiful countryside. This 18th century grade-II listed property is right beside the River Seven, in the picturesque village of Sinnington, and the North York Moors National Park. The cottage is full of original character, whilst having all the amenities needed for a relaxing break. Many amazing walks can be enjoyed from right outside the door and the wonderful village pub and restaurant is only a few minutes walk away.

FamilyValuePets

4.97 out of 5 average rating, 158 reviews
Top guest favorite
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

Characterful and quaint 3 bedroom Grade II listed cottage, built in 1800 with open plan living. Within easy walking distance of many shops, tea rooms, restaurants, pubs and the castle, there is parking very close by. Castlegate cottage is a perfect base for exploring the many local attractions and places of interest, such as The Steam railway, Beck Isle museum, The North Yorkshire Moors, Whitby, Scarborough, Flamingo Land, Eden Camp, Dalby Forest and York.

LocationFamilyView

4.93 out of 5 average rating, 417 reviews
Guest favorite
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.

FamilyLocationView

4.82 out of 5 average rating, 105 reviews
Guest favorite
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.

FamilyValueQuiet

4.86 out of 5 average rating, 154 reviews

Popular amenities for Helmsley cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favorite
The exterior of the historic limestone cottage is showcased, featuring a charming blue door framed by elegant brickwork. Two large windows allow natural light to illuminate the front. Lush greenery surrounds the property, with neatly trimmed hedges leading to a paved path.
Cottage in Langton

Historic 18th Hussars Cottage with a Modern twist

ValueLocationGetting around

4.89 out of 5 average rating, 284 reviews
Top guest favorite
A charming bedside table is positioned next to a spacious bed, featuring an antique scale as a unique lamp. The textured sandstone wall provides a warm backdrop, complementing the soft hues of the furniture and bedding.
Cottage in Burythorpe

Historic cottage, wood-fired hot tub + village pub

ValueLocationHiking

4.98 out of 5 average rating, 219 reviews
Superhost
A hot tub is positioned on a paved area, surrounded by gravel and wooden fencing. Lush greenery is visible in the background, with a cloud of steam rising from a passing steam locomotive, creating a unique view. Outdoor seating can be seen nearby.
Cottage in Newbridge

3 Railway Cottage Pickering , Hot Tub, Pets all'd

LocationValueHospitality

4.9 out of 5 average rating, 197 reviews
Top guest favorite
A well-maintained garden area is featured, with a private hot tub and seating under an umbrella. Flowering lavender lines the path, and the wooden fence provides privacy. A decorative window accentuates the space, contributing to a serene outdoor environment.
Cottage in Welburn

Luxury Cottage close to Castle Howard with hot tub

ValueFamilyPets

4.99 out of 5 average rating, 124 reviews
Guest favorite
A comfortable bedroom features a king-sized bed with a decorative patterned headboard. Soft pillows and a green throw blanket are arranged neatly on the bed. Two bedside lamps provide gentle lighting, and a large window offers views of the countryside beyond.
Cottage in Ainderby Steeple

Luxury Farm Cottage with Hot Tub in Yorkshire

FamilyLocationCheck-in

4.98 out of 5 average rating, 110 reviews
Top guest favorite
An inviting living area is showcased with a leather Chesterfield sofa adorned with plaid cushions. A wooden dining table is surrounded by chairs, positioned against a warm brick wall, while a well-equipped kitchen with granite countertops is partially visible.
Cottage in Skirpenbeck

Morgan Cottage - Env Friendly - Private Hot Tub

FamilyLocationNearby

4.93 out of 5 average rating, 214 reviews
Superhost
An outdoor courtyard is presented with a hot tub, framed by greenery and stone walls. A wooden table holding a teapot and cups adds a cozy touch. Decorative elements like pinecones and flowers enhance the space, inviting relaxation in this private setting.
Cottage in North Yorkshire

La Fenetre Holiday Cottage

FamilyValueGetting around

4.81 out of 5 average rating, 534 reviews
Top guest favorite
The stone exterior of Gable End Cottage features a charming combination of textures, with large windows allowing natural light to flood in. A well-maintained garden with a gravel pathway leads to the entrance, creating a welcoming approach surrounded by greenery.
Cottage in Scotton

Dog friendly cottage & hot tub

LocationFamilyHiking

4.95 out of 5 average rating, 232 reviews

Pet-friendly cottage rentals

Top guest favorite
A cozy living area features two sofas in yellow and green, arranged around a wooden coffee table. A log burner is positioned in the corner, and a large TV is mounted on the wall. Natural light filters in from the high window adorned with a patterned blind.
Cottage in Husthwaite

The Stable, Husthwaite

ValueFamilyQuiet

5.0 out of 5 average rating, 101 reviews
Top guest favorite
The exterior of a characterful Yorkshire longhouse is displayed, showcasing stone walls and a tiled roof. Flower baskets hang from the front, adding a touch of color. The entrance features a light-colored door framed by two potted plants. Windows reflect a welcoming ambiance.
Cottage in North Yorkshire

Spacious character historic cottage

LocationFamilyTV

4.95 out of 5 average rating, 139 reviews
Top guest favorite
The cottage is constructed of traditional stone, showcasing a quaint exterior with a pitched roof and chimney. Two large windows with flower boxes frame the entrance, which features a light-colored door. The surroundings include a peaceful street lined with other characterful buildings.
Cottage in North Yorkshire

Cosy character cottage in heart of Pickering

LocationFamilyParks

4.91 out of 5 average rating, 387 reviews
Guest favorite
A comfortable lounge area features a pink sofa, a red chair, and wooden flooring. A staircase with wooden banisters leads to the upper level. A dining table with white chairs sits in the background, complemented by a simple wall decoration and a standing lamp.
Cottage in Kirkbymoorside

Fuchsia Cottage- a cosy getaway

ValueFamilyBeach

4.87 out of 5 average rating, 522 reviews
Top guest favorite
A cozy sitting room is presented with a large mirror reflecting warm light from a chandelier. A television is positioned across from a log burner, surrounded by two armchairs and a comfortable sofa. Soft gray tones and decorative cushions contribute to the welcoming ambiance.
Cottage in Stokesley

Apple Tree Cottage. Stokesley.North Yorkshire.

FamilyLocationBiking

4.91 out of 5 average rating, 330 reviews
Top guest favorite
An open dining area is filled with natural light from skylights and large windows. A table set for dining is surrounded by several light-colored chairs. A view of a private deck can be seen through the patio doors, accompanied by vibrant floral arrangements on the table.
Cottage in Commondale

Winnow Cottage . in the Heart of the NY Moors

LocationValueCondition

4.94 out of 5 average rating, 161 reviews
Guest favorite
Cottage in North Yorkshire

Cosy ‘Cobblers Cottage’ - Pickering

FamilyLocationCheckout

4.82 out of 5 average rating, 345 reviews
Top guest favorite
A cozy sitting room is featured with a log burning stove as the focal point, flanked by built-in shelves displaying books and decorative items. Gentle lighting from lamps enhances the calming ambiance, while a patterned area rug adds texture to the stone floor.
Cottage in Sheriff Hutton

English country cottage on village green

LocationFamilyDecor

4.93 out of 5 average rating, 213 reviews

Private cottage rentals

Top guest favorite
The exterior of Manor House Cottage is framed by lush greenery and colorful flower beds. A well-kept lawn stretches in front, leading to the brick facade of the cottage, which features multiple windows and a welcoming entrance surrounded by trees.
Cottage in Thirsk

Manor House Cottage self catering rural location

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 166 reviews
Top guest favorite
A detached holiday cottage features a red front door and distinctive round window, set against a backdrop of textured brick walls. The surrounding area is landscaped with greenery, and gravel provides off-road parking in front of the building.
Cottage in North Yorkshire

APRICOT COTTAGE - A LUXURY HOLIDAY COTTAGE

FamilyLocationCleanliness

4.93 out of 5 average rating, 398 reviews
Top guest favorite
The exterior of Rowans Cottage is showcased with a traditional stone façade and a red-tiled roof. A wrought-iron fence surrounds the property, complemented by greenery. Large windows allow natural light to illuminate the inviting entrance, presenting a charming rural setting.
Cottage in Lockton

Rowans Cottage - distinctive 1 bed restoration

ValueFamilyBathroom

4.98 out of 5 average rating, 103 reviews
Top guest favorite
The entrance to Fernbeck Cottage is framed by a stone facade, with a wooden door painted in a calm green hue. A brass mailbox is mounted beside the door, and a small sign identifying the cottage hangs above. Lush plants are arranged beside the entrance.
Cottage in Darley

Country cottage in the Yorkshire Dales

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 416 reviews
Superhost
The exterior of a charming cottage is displayed, featuring a warm stone façade and a blue front door. Small windows with lace curtains frame the entrance, while planters with greenery enhance the inviting look. The quiet street is lined with neighboring houses of similar architecture.
Cottage in Kirkbymoorside

Cosy Country Cottage Sleeps 4

FamilyValueOutdoor spaces

4.78 out of 5 average rating, 140 reviews
Top guest favorite
The exterior of the building is showcased, featuring stone walls and a traditional red tile roof. Windows are framed in white, reflecting a classic style. A small bench is visible near the entrance, and a stone wall borders the pathway leading to the welcoming entrance.
Cottage in Danby

Farm Cottage with Stunning Views.

ValueFamilyLaundry

4.99 out of 5 average rating, 586 reviews
Top guest favorite
A charming cottage is seen, featuring a red brick exterior with white window frames. Lush greenery surrounds the property, which is set back from a well-maintained lawn. Climbing plants adorn the front wall, contributing to a serene outdoor landscape.
Cottage in Ripon

Matchbox Cottage Grade II listed building -Ripon

LocationValueBathroom

4.94 out of 5 average rating, 230 reviews
Top guest favorite
Cottage in North Yorkshire

Katiann's Cottage

ValueFamilyLaundry

4.98 out of 5 average rating, 189 reviews

Destinations to explore