House vacation rentals in Helmsley

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Top-rated house rentals in Helmsley

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Top guest favorite
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
4.98 out of 5 average rating, 107 reviews

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.

Top guest favorite
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
4.96 out of 5 average rating, 104 reviews

Little Hillside

A cosy cottage nestled in the hills of the North Yorkshire Moors, on the edge of Ampleforth village. An ideal place to go off grid, listen to the wildlife and enjoy the beautiful countryside. York is 20 miles away with countless tourist attractions and less than 10 minutes drive is the pretty market town of Helmsley with lots to explore. There is an abundance of great walks from your doorstep, excellent cycling routes and you will be spoilt for choice with fantastic cafes, pubs and restaurants.

Top guest favorite
A spacious living area features a green sectional sofa and a complimentary armchair. A coffee table is centered on a woven rug, with a decorative ladder parallel to a shelf adorned with plants. Large windows allow ample natural light, framed by green accents.
Home in North Yorkshire
4.97 out of 5 average rating, 112 reviews

The Bothy

Adults only/no pets..our Ethos ..to make your visit relaxing, recharge your batteries, revisit..all in a peaceful setting but don’t take our word for it..read our Reviews! We may not have cooking facilities but Pickering has some great eateries and pubs…what we do have is a kettle/coffee machine/fridge/BBQ Discounts for sun-thurs and early bookings…don’t delay book today! Come to beautiful North Yorkshire so much to see and do you may never want to leave! A warm welcome awaits you at The Bothy

Top guest favorite
A cozy snug room is presented with a blue sofa featuring decorative cushions, accompanied by a striped armchair with an orange accent pillow. Two lamps provide soft lighting, and a round mirror is mounted on a green accent wall, enhancing the inviting ambiance.
Home in North Yorkshire
4.98 out of 5 average rating, 202 reviews

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.

Top guest favorite
The exterior of Granary Lodge is displayed, featuring a traditional stone façade with a red door. A sloped roof and multiple windows complement the building, surrounded by well-maintained landscaping and a gravel driveway leading to the entrance.
Home in Thirsk
4.99 out of 5 average rating, 117 reviews

Spacious two bedroom country property

Granary Lodge is situated on a quiet lane, yet less than two miles from Thirsk; a busy, attractive market town. It is spacious with a large lounge, kitchen, a double bedroom (ensuite bathroom) and a twin room. Also, a shower room with basin and toilet. Enjoy the use of your private patio seating area with views over the owners garden and pond. A larger garden area and further seating is also available for guest use. Local good pub (15 mins walk). N York Moors National Park: 15 mins drive.

Top guest favorite
A private courtyard garden features a gravel path surrounded by lush greenery and various potted plants. French doors, framed by climbing foliage, open to the cottage, inviting natural light. A small table and chairs are visible, creating a serene outdoor space for relaxation.
Home in West Yorkshire
4.89 out of 5 average rating, 247 reviews

Garden Cottage - Central Wetherby

This delightful, characterful three bedroomed cottage is located in the very heart of the beautiful market town of Wetherby. It is situated close to all local amenities, tastefully furnished with onsite parking and a mature, private courtyard garden Wetherby town centre with its extensive range of coffee shops, restaurants, bars and shops is only 2 minutes from your front door. Also gorgeous river walks, beautiful riverside parks and local cinema and indoor pool are just on your doorstep.

Guest favorite
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
4.9 out of 5 average rating, 438 reviews

Oakforge Cottage, a spacious home from home.

Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.

Top guest favorite
A dining area is visible below, featuring a glass table set for two with plates and utensils. Two elegant chairs frame the setting, complemented by a nearby decorated Christmas tree. Exposed wooden beams above add character to the space, enhancing the modern design.
Home in North Yorkshire
4.88 out of 5 average rating, 214 reviews

Cosy Yet Spacious Home. Short Stroll To Centre

Enjoy a clean, comfortable, cosy yet spacious, experience at this peacefully located, budget friendly holiday home. Just a very short stroll away from Pickering town centre with a whole host of shops, cafes, bars, pubs and restaurants. Offering a stylish, comfortable space with all you need. Ideal as a base to enjoy and explore all great North Yorkshire has to offer. Free on street parking subject to availability or car park with ev chargers less than 300 meters away.

Guest favorite
An elegant freestanding bathtub sits against a rustic stone wall featuring exposed wooden beams. A potted plant is positioned nearby, adding a touch of greenery to the serene setting. The smooth tile floor enhances the bathroom's spacious feel.
Home in Malton
4.93 out of 5 average rating, 185 reviews

Luxury one bedroom cottage with log burning hot tu

Relax and unwind in the newly refurbished one bed Irishman's Cottage. The cottage retains many old features and is surrounded by the rolling hills of the Yorkshire Wolds. The living space is open plan with ample space for a couples retreat or family break away. In the summer months dine al fresco and enjoy a BBQ on the private patio besides the wood burning hot tub. A short walk away is our private lake, where you might catch site of a resting deer or hare!

Top guest favorite
The cottage exterior showcases a charming brick facade with a sloped red roof. Bright flowering plants in various colors surround the entrance, enhancing the natural setting. Two skylights are visible on the roof, allowing light into the interior.
Home in Pilmoor
4.98 out of 5 average rating, 448 reviews

The Salt House Cottage, Pilmoor

Guests have a small private grassed area with a table and chairs. The cottage has dishwasher, washing machine and wood burning stove, all logs included. We do not accept pets. In summer, when the swing seat is out, guests have access to the main garden. The cottage has no internet connection but depending on your network, a good 3G or 4G signal can be accessed. We do not accept bookings from people who smoke or vape. Check in from 2pm, check out 10am.

Guest favorite
A charming stone barn features a warm terracotta roof and large windows allowing natural light to enter. The outdoor space includes a small metal table with two chairs, set on the green lawn, ideal for enjoying a pleasant morning or afternoon.
Home in Hovingham
4.92 out of 5 average rating, 237 reviews

The Shed, Hovingham, York

An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.

Guest favorite
The exterior of a stone cottage is framed by two lush trees, with a clear blue sky overhead. A gravel path leads to a wooden front door, flanked by large windows. A bistro-style chair and table are positioned on the lawn, which is spacious and well-maintained.
Home in North Yorkshire
4.88 out of 5 average rating, 233 reviews

Rural homely cottage in North York Moors

Cosy cottage located in the North York Moors National Park with gorgeous big skies! A super base for exploring castles, abbeys, villages and the Heritage coast. Spoilt for choice in eateries from great local pubs to Michelin starred restaurants all with a 10 mile radius. Many guests comment on how peaceful and calm their stay has been. My place is good for couples, solo adventurers, families with children and pets (one, well behaved dog only).

Popular amenities for Helmsley house rentals

Quick stats about house rentals in Helmsley

  • Total vacation rentals

    Explore 10 vacation rentals in Helmsley

  • Nightly prices starting at

    Helmsley vacation rentals start at G$29,282 GYD per night before taxes and fees

  • Verified guest reviews

    Over 550 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    10 of Helmsley vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Helmsley rentals

  • 4.9 Average rating

    Helmsley stays are highly rated by guests—averaging 4.9 out of 5!

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