Vacation rentals in Helmsley

Apartment in West Yorkshire

A bright and airy living area features a large window with patterned curtains, providing natural light. A dining table with chairs sits alongside a cozy seating arrangement, which includes two sofas and a TV stand. Neutral tones create a calming environment.

5 out of 5 average rating, 3 reviews

Penthouse In The Heart of City

Forget your worries in this spacious and serene space. Situated in the Heart of Wakefield, Rhubarb Loft, has the space, peace and quiet of a country apartment, yet just two minutes from the hustle and bustle of a vibrant City Centre. Rhubarb Loft is a Penthouse in a former home of the Lord Mayor of Wakefield. The building is full of character, so unfortunately no elevators. With its own entrance, your privacy is assured and there's plenty of space inside as well. Two bedrooms with up to 4 beds.

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, 83 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, 137 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

4.87 out of 5 average rating, 179 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.

5 out of 5 average rating, 26 reviews

Home in Skipton

Craven Vue - Highly rated home with EV Charger

NEW for 2025 is a Hypervolt Home 3 Pro EV Charger for guests to use. 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.

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, 189 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, 129 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.

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

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Helmsley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Helmsley's top sights

Helmsley Walled Garden36 locals recommend

Duncombe Park8 locals recommend

Feversham Arms Hotel & Verbena Spa4 locals recommend

The Feathers Hotel4 locals recommend

Hunters of Helmsley4 locals recommend

La Trattoria4 locals recommend

Other great vacation rentals in Helmsley

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.

4.83 out of 5 average rating, 23 reviews

Seaview Retreat Crimdon Dene

4.93 out of 5 average rating, 30 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

5 out of 5 average rating, 11 reviews

A decorative tray is arranged on a bed, featuring a lantern, a candle, and small vases with neutral-toned flowers. Soft linens are displayed on the bed, with natural light filtering through sheer curtains, creating a serene and calming atmosphere.

Home in Stockton-on-Tees

Modern large home for families and contractors

4.96 out of 5 average rating, 158 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 ..

4.98 out of 5 average rating, 55 reviews

A narrow cobbled street is lined with historic timber-framed buildings, featuring charming shopfronts. Signs for local businesses hang from the structures, while visitors stroll along the walkway. The area captures the essence of York's medieval architecture and vibrant atmosphere.

Home in York

Beautiful 2-Bed Home Close to the Centre of York