House holiday rentals in Helmsley

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Top-rated house rentals in Helmsley

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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
4.98 out of 5 average rating, 108 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 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
4.96 out of 5 average rating, 108 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 favourite
A charming Victorian stone cottage stands against a backdrop of greenery. The cottage features a mix of dark stone and light brick, with a small front porch and a sloped garden area. Two large windows allow natural light to enter the welcoming interior.
Home in Pickering
4.97 out of 5 average rating, 117 reviews

Stationmaster's Cottage

A detached Victorian stone cottage in the shadow of Pickering Castle and overlooking North York Moors Railway station, this characterful property with real fire is only 3 minutes walk away from town centre amenities, the castle and a ten minute walk to the start of the Tabular Hills way and gateway to the North York Moors National Park. Free parking is provided in the Platform 3 Car Park diagonally opposite the property 70 yards away (dashboard pass provided). Please note: steep stepped access.

Top guest favourite
Home in Beadlam
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 favourite
The exterior of a rustic brick building is surrounded by lush greenery and vibrant flowering plants. A spacious wooden dining table sits on a patio, inviting outdoor meals. The entrance features double doors, framed by wisteria and climbing roses, enhancing the welcoming appeal.
Home in Alne
4.99 out of 5 average rating, 104 reviews

The Old Post Office pretty village 20min from York

The Old Post Office, providing a lovely 3 bedroom character suite, with private, off road parking and a sunny private courtyard to enjoy outside eating and relaxation.. Situated in the beautiful village of Alne, 10 miles from York and access to Harrogate, the Dales, the North York Moors and the Coast. The Area has just been awarded "one of the Best Places to Live in the UK" by The Sunday Times. Stylish, Egyptian cotton bedding on all beds and providing everything you will want for your stay.

Top guest favourite
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 South Kilvington
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 favourite
A dual aspect lounge showcases large windows framing scenic countryside views. A stylish desk and chairs are set beside a low coffee table, inviting work or relaxation. The space is complemented by warm lighting and rich wooden furniture, creating a calming environment.
Home in Richmond
4.98 out of 5 average rating, 153 reviews

Treetops Cottage @ Treetops Hideouts

Treetops Cottage is a luxury country retreat just one mile from bustling Richmond nestled in a private, stunning setting. The newly refurbished property boasts exceptional far reaching views across the rolling countryside and the south facing patio is a fantastic space to watch the wild deer that come up from Sandy Beck. Ideally located alongside Brokes giving direct access to the beautiful surrounding countryside, the property offers luxury living with great days out on your doorstep.

Top guest favourite
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 Pickering
4.88 out of 5 average rating, 217 reviews

Short stroll to pubs, cafés & shops. Free Parking

Enjoy a clean and comfortable, cosy yet spacious, experience at this peacefully located holiday home. Just a very short stroll from Pickering town centre where you’ll be spoilt for choice 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 or free parking permit for Eastgate car park which is less than 300 meters away.

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
4.9 out of 5 average rating, 439 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.

Guest favourite
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 Coulton
4.91 out of 5 average rating, 244 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 favourite
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 Oldstead
4.88 out of 5 average rating, 236 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).

Guest favourite
Home in Sutton-under-Whitestonecliffe
4.92 out of 5 average rating, 231 reviews

Lovely cottage with sunny garden sleeps 6

A lovely cottage with a large oak floored living area with 360 degree turning log burner with double sets bi fold oak doors to an enclosed patio with seating, bbq and fire pit and grassed enclosed garden. There is another log burner in the snug sitting room. Bedroom 3 has an en-suite and bedrooms 1 and 2 share a bathroom with a walk in shower. Parking for 2 cars - self check in.

Popular amenities for house rentals in Helmsley

Quick stats about house rentals in Helmsley

  • Total holiday rentals

    Explore 10 holiday rentals in Helmsley

  • Nightly prices starting at

    Helmsley holiday rentals start at $179 SGD per night before taxes and fees

  • Verified guest reviews

    Over 550 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Helmsley holiday rentals include wifi 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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