Vacation rentals in Helmsley

4.99 out of 5 average rating, 150 reviews

A cozy living area features a comfortable sofa and a wooden coffee table. Large glass sliding doors open to a deck with outdoor seating and an umbrella, providing a view of the serene lake and surrounding landscape.

Cabin in Filey

Secret Of Eden Lake View Lodge - Pets/Beach/E.V

The Lake View Lodge is located on the new Meadows development. It is pet friendly and has a country theme inside. We have a log burner, two en-suites and an open planned kitchen/living space. We also have Wi-Fi, board games/Netflix/Disney+/Xbox Series S/Homepod. It’s a short walk to the beach. On site facilities include a leisure centre with gym & swimming pool, tennis court, wildflower meadow, children's play area, archery, pub, restaurant, pharmacy, beautician and more. Free E.V charging!

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

5 out of 5 average rating, 26 reviews

Home in Skipton

Craven Vue - Highly rated home with EV Charger

EV CHARGER IS AVAILABLE FROM 25/4/25 AT AN ADDITIONAL COST OF £10 PER NIGHT. In central Skipton, Craven Vue is a HIGHLY RATED, character 2 bedroom former mill workers cottage on a level street in the Middle Town conservation area of Skipton. The cottage is tastefully decorated and equipped with good quality furnishings and appliances to ensure that it is comfortable for your stay. Located 5 minutes walk from Skipton's historic High Street, Skipton Castle and the Leeds - Liverpool Canal.

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.

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, 188 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.

Apartment in North Yorkshire

An inviting open plan living area is featured, highlighted by a bright yellow wall and natural light streaming through skylights. A dining table is set for four, while two cozy settees and a coffee table create a comfortable space for relaxation. A television is positioned on a low media unit.

4.93 out of 5 average rating, 145 reviews

The Old Sweet Factory - Town Centre Apartment

Refurbished, spacious and characterful second floor two bedroom apartment, centrally located in the Spa town of Harrogate. The apartment has recently been renovated to a high and exacting standard, is completely self-contained and contains everything you might need for a comfortable break. Located in the beautiful Montpellier quarter, the Harrogate International Conference and Convention centre and The Royal Hall is within 1 minutes walk away.

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

Quaint homes, peaceful surroundings

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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, 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

4.83 out of 5 average rating, 12 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

4.93 out of 5 average rating, 29 reviews

Home in Seacroft

Elegant Home In Yorkshire: free parking & wifi.

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

4.96 out of 5 average rating, 157 reviews

An outdoor patio area features a curved seating arrangement made of wicker and a wooden dining table surrounded by multiple chairs. Lush greenery lines the space, with trees and shrubs providing shade. A clear blue sky completes the serene atmosphere.

Home in Runswick Bay

Outstanding detached holiday home ..

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