Cottage holiday rentals in Helmsley

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Quick stats about cottage rentals in Helmsley

  • Total holiday rentals

    Explore 30 holiday rentals in Helmsley

  • Nightly prices starting at

    Helmsley holiday rentals start at $217 SGD per night before taxes and fees

  • Verified guest reviews

    Over 890 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Helmsley holiday rentals include wifi 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 favourite
Cottage in Welburn

Luxury Country Cottage Hot Tub Spa Retreat | York

Snowdrop Cottage is a luxurious 5★ retreat nestled in the picturesque village of Welburn, surrounded by the breathtaking Howardian Hills, just minutes from the iconic Castle Howard, the city of York and the Yorkshire coastline. An idyllic escape, this beautifully styled boutique cottage features a private garden spa & hot tub, cosy log burner & romantic four-poster king-size bed - the perfect setting for couples, families and dog walkers to relax, reconnect and explore the Yorkshire countryside.

FamilyLocationKitchen

4.98 out of 5 average rating, 129 reviews
Top guest favourite
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

31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, steam railway, the coast and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

ValueLocationQuiet

4.92 out of 5 average rating, 391 reviews
Top guest favourite
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

FamilyValueWalkability

4.96 out of 5 average rating, 192 reviews
Top guest favourite
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

Manor House Cottage is located in the small hamlet of Holme-On-Swale 7 miles from the market town of Thirsk which is known for its connection to James Herriott and within easy reach of North Yorkshires National Parks. Set within the grounds of the Manor House, It is a quirky upside down cottage with a well appointed modern kitchen, two bedrooms and bathroom on the ground floor with sitting room upstairs, private garden with table and chairs. There are no other holiday cottages in the grounds.

FamilyValueAccess

4.99 out of 5 average rating, 170 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.

FamilyLocationAccuracy

4.94 out of 5 average rating, 104 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

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!

ValueFamilyAccuracy

4.98 out of 5 average rating, 349 reviews
Top guest favourite
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.

ValueFamilySolo travel

4.94 out of 5 average rating, 166 reviews
Top guest favourite
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."

FamilyValueHeating

4.99 out of 5 average rating, 119 reviews
Top guest favourite
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.

LocationFamilyLaundry

4.97 out of 5 average rating, 158 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.

LocationFamilyHiking

4.82 out of 5 average rating, 106 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.

LocationFamilyCheck-in

4.86 out of 5 average rating, 154 reviews
Top guest favourite
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

Husthwaite is a quaint village 17 miles North of York and just off the A19 . The cottage is tucked away on a private drive. We are close to the North York Moors perfect for scenic country walks. The village has a Church, St. Nicholas' dating from the twelfth century next to the Village Green which forms the centre of the village. Our local pub The Plum & Partridge is just 5 mins walk where they serve great beer and fabulous food.

ValueFamilyAmenities

5.0 out of 5 average rating, 101 reviews

Popular amenities for cottage rentals in Helmsley

Cottage rentals with a hot tub

Private cottage rentals

Top guest favourite
A charming stone cottage features roses climbing the walls under a clear blue sky. Well-maintained gardens include neatly trimmed shrubs and vibrant flowers, providing a welcoming entrance. Paved stones lead to the front door, enhancing the appeal of the outdoor space.
Cottage in Thorp Arch

Secluded country cottage with private gardens

LocationValueAccess

5.0 out of 5 average rating, 209 reviews
Top guest favourite
A well-appointed bedroom features a spacious bed adorned with neutral bedding and a soft quilt. A tray with fresh fruit and snacks rests on the bed. Light from a bedside lamp illuminates the cozy ambiance, while a dresser and neatly organized cabinets provide storage.
Cottage in North Yorkshire

Barn in North Yorkshire near York & Coast

LocationFamilyLong stay

4.95 out of 5 average rating, 430 reviews
Top guest favourite
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

FamilyValueLaundry

4.93 out of 5 average rating, 401 reviews
Top guest favourite
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

LocationFamilyHospitality

4.98 out of 5 average rating, 104 reviews
Top guest favourite
Cottage in North Yorkshire

Luxury Old Stone Cottage, Beautifully Presented

LocationValueGetting around

4.88 out of 5 average rating, 162 reviews
Top guest favourite
Cottage in Bewerley

The End Place - A romantic hideaway for two

ValueLocationNearby

5.0 out of 5 average rating, 391 reviews
Top guest favourite
A spacious bedroom is presented with a superking-sized bed, adorned with a decorative quilt and neatly arranged towels. Natural light enters through a window, framed by light blue curtains, highlighting the soft carpet and a wooden dresser beside a cozy armchair.
Cottage in Ryton

Peace & Luxury, stunning rural views near Malton

ValueLocationHeating

4.97 out of 5 average rating, 110 reviews
Top guest favourite
A charming stone pathway leads to a rustic brick cottage, surrounded by well-tended gardens featuring a variety of plants and flowers. Two wooden garage doors are visible beside the cottage, while a wrought iron railing adds a classic touch to the outdoor space.
Cottage in Stillington

Moxby Priory Cottage - An idyllic rural escape

ValueLocationAccuracy

4.93 out of 5 average rating, 131 reviews