Vacation rentals in Helmsley

Cottage in North Yorkshire

The exterior of Bancroft Cottage is highlighted by a charming entrance with wooden doors and a pitched roof. A small outdoor seating area with two chairs and a table sits on gravel, surrounded by greenery. The welcoming façade is complemented by clear blue skies.

4.99 out of 5 average rating, 160 reviews

Bancroft Cottage: Luxury Holidays Yorkshire

Bancroft Cottage is a luxury, self-contained holiday cottage set within the grounds of Bancroft, the main house. It is a hidden jewel found within the historic Yorkshire market town of Bedale, commonly referred to as the ‘Gateway to the Dales’ The property is perfectly situated to offer guests the ease of walking to shops, restaurants and pubs via its own private access whilst being only a short ride away from the magnificent Yorkshire Dales, North York Moors, Harrogate and the city of York.

4.98 out of 5 average rating, 82 reviews

Home in Staithes

Beautifully Renovated Cottage next to Beach

Bay Tree Cottage is located in a peaceful location a stones throw away from the beach and the Cod & Lobster with the other village amenities only a short stroll away. The spacious cottage has been fully renovated throughout to a high standard. It features a wood burning stove, a great outside area and the sea views from the master bedroom are breathtaking. It is suitable for couples & families alike, ideal for both relaxing or a more energetic break, for example walking the Cleveland Way.

4.99 out of 5 average rating, 136 reviews

Home in Burton Leonard

Luxury 3 bedroom house - hot tub & amazing view!

Yoredale House is a stone-built 3 bedroomed detached property with amazing views set in its own grounds with a 5-person hot tub - just outside the beautiful village of Burton Leonard. Furnished to the highest standards with panoramic views towards the North Yorks Moors. Easy access to two National Parks, Fountains Abbey, Herriot country, Ripon, Harrogate, York etc. Two village pubs and shop within walking distance. Great base for walking, cycling and exploring beautiful North Yorkshire.

Cottage in Robin Hood's Bay

4.88 out of 5 average rating, 178 reviews

Cosy 2 Bed Seaside Cottage, Robin Hoods Bay Whitby

A cracking home from home, The Old Bakehouse Cottage in Sunny Place, Robin Hoods Bay, is a curl-up-with-a-book sort of place with the North Sea just round the corner crashing against the sea walls. But when the tide retreats the beach is a world of rock pools, fossil hunting and numerous coastal walks will await. Yorkshire Holiday Cottage 4 star accommodation" exceptional standard of cleanliness, décor and historic feel to the place”. Fast WIFI, Car Parking permit included. Beach 250 yards

Farm stay in North Yorkshire

4.93 out of 5 average rating, 28 reviews

Sunset Retreat, Fabulous Farm Stay

Get away from it all when you stay under the stars. Take it easy at this unique and tranquil getaway. Sunset Retreat with views over luscious, open countryside and a superb location for exploring the Moors, Heritage Coast and all the Seaside amenities of Scarborough. This Luxury Glamping Pod has quality fixtures and fittings to get you through your holiday in Yorkshire. It is well-suited to Couples looking to get away and explore the beautiful walking country surrounding the area.

4.98 out of 5 average rating, 42 reviews

A compact sleeping area features a cozy bed adorned with a patterned duvet. Two bedside lamps are positioned on either side of the bed, while checkered curtains frame a window high on the wall, allowing natural light to fill the space.

Apartment in Scarborough

Southcliff Retreat

Bring the whole family to this spacious retreat with lots of room a whole family to relax in plenty of space. This quiet first floor apartment is located minutes off the idyllic Esplanade. Beautiful walks are on your doorstep, the serene Italian gardens are a couple of minutes away. The beach is a short walk through the south cliff gardens. The Town centre is within your reach making this a perfect base for a relaxing holiday. Parking outside the apartment is ample and free.

Apartment in North Yorkshire

A narrow street features traditional buildings with a mix of storefronts and residential spaces. People can be seen walking along the cobblestone path, while chimney stacks rise above the rooftops, contributing to the charming atmosphere of the area.

4.96 out of 5 average rating, 251 reviews

17a Grape Lane, Whitby

17a Grape Lane offers the very best in holiday accommodation - a central location, a beautiful listed building, harbour views and a comfortable and stylish home from home. It’s a tasteful, luxurious and comfortable self-catering holiday apartment set out over two floors. With a huge lounge, a fitted kitchen with dining area and two generous bedrooms, two bathrooms and a downstairs toilet and fantastic harbour views, you’ll have space to really relax and enjoy your stay.

Shepherd’s hut in Goathland

A private hot tub sits under the shade of a canopy, surrounded by natural greenery. In the background, two outdoor chairs face a scenic view of rolling hills and trees, offering a tranquil setting for relaxation.

4.99 out of 5 average rating, 186 reviews

Escape into Nature - Owl

Stay in one of our two shepherds huts and enjoy the splendour of the national park. Situated alongside walking routes & the 'Rail Trail' former railway of 1836 which takes you on a wonderful adventure around the beauty of the park across rivers, streams, waterfalls & all that nature provides. We offer a piece of country life in our Shepherd huts. Ideal for those who want to escape, we are completely off the beaten track! Switch off & relax back to nature.

4.89 out of 5 average rating, 126 reviews

An outdoor play area is equipped with green turf, featuring a small pond surrounded by rocks and tropical plants. Large shaded canopies provide relief from the sun, creating a comfortable environment for relaxation and fun.

Home in Cayton Bay

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

Beautiful and brand new, fully equipt, high-end, luxury caravan. A perfect place to relax or bring the whole family. 5 minutes walk to the sea. Parkdean onsite entertainment for children and adults. swimming onsite, high ropes, arcades, and many more activities. With Cayton Bay minutes away from the caravan, Filey, Scarborough and Bridlington are not far away via car or Park & Ride, again minutes away from the caravan.

4.95 out of 5 average rating, 20 reviews

A spacious living area is presented with two comfortable sofas facing a coffee table. A large window allows natural light to fill the room, while decorative curtains frame the view. A flat-screen TV is positioned on an elegant stand, and a stylish mirror enhances the ambiance.

Home in Middlethorpe

No. 1 - Laurel Cottage

This gorgeous, two bedroom cottage is located in a beautiful, peaceful area of York. Having been finished to a very high standard with nothing but comfort in mind, this lovely home away from home boasts a country feel while still located within York. Featuring all new amenities, this beautiful Airbnb provides the perfect base from which to explore this city.

Apartment in North Yorkshire

The view from the interior shows an outdoor terrace with wooden decking and various potted plants. Steps lead from the terrace to a garden area with a decorative railing. Large glass doors open the space to the outdoor setting.

5 out of 5 average rating, 3 reviews

Seadream 1 bedroomed with Private HOT TUB

Stunning location views accommodation a beautiful place for a romantic getaway for 2 guests ( 1 fully housetrained small breed dog may be allowed on request only prior to booking you must request prior to booking as its a request only basis it is not guaranteed thank you

Vacation rentals for every style

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Cottages

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A space thats all yours, with room for everyone

Hotels

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Popular amenities for Helmsley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Helmsley's top sights

Helmsley Walled Garden21 locals recommend

Duncombe Park14 locals recommend

Feversham Arms Hotel & Verbena Spa9 locals recommend

The Helmsley Arts Centre8 locals recommend

The Feathers Hotel8 locals recommend

Mannion & Co8 locals recommend

Other great vacation rentals in Helmsley

5 out of 5 average rating, 24 reviews

An enclosed outdoor area features a garden furniture set that accommodates up to eight people. An umbrella provides shade over the rectangular table, while artificial grass and paved stone flooring contribute to the space's comfort and practicality.

Home in Bempton

Chance Escapes

5 out of 5 average rating, 3 reviews

The living area is furnished with comfortable, soft seating arranged around a central coffee table. A flat-screen television is mounted on the wall, and a decorative electric fireplace adds warmth. Natural light filters in through the windows, framed by light curtains.

Cabin in Wilberfoss

Elckys Lodge - Hot Tub Retreat Near York

4.95 out of 5 average rating, 20 reviews

A balcony view is presented, showcasing a serene estuary framed by lush greenery. Two seating areas made of dark wicker are visible, complemented by the blue sky. The patio doors open outward, allowing natural light to fill the space.

Home in North Yorkshire

Riverside Cottage

4.82 out of 5 average rating, 11 reviews

The exterior of a rustic brick building is featured, showcasing a charming entryway with a dark wooden door. Surrounding greenery adds a touch of nature, while the cobblestone driveway leads to a welcoming entrance. Large windows hint at the interior's natural light.

Barn in Green Hammerton

The Barn Gowlands Farm

Camper/RV in Blackhall Colliery

A comfortable outdoor seating area is displayed, featuring a wicker sofa adorned with decorative pillows. A glass-topped table sits beside a potted plant, offering a clear view of the sea in the background. Bright yellow gorse flowers add color to the landscape.

4.86 out of 5 average rating, 22 reviews

Seaview Retreat Crimdon Dene

4.89 out of 5 average rating, 28 reviews

Cottage in Filey

Prospect Cottage - The Bay Filey - 2 bedrooms

4.88 out of 5 average rating, 8 reviews

A living area features two beige sofas arranged around a light-colored rug. A small side table, a television, and a decorative mirror are also present. Black-and-white photographs adorn the walls, while a modern chandelier provides overhead lighting.

Home in Eaglescliffe

Home and away