Self Catering Holiday Cottages in Helmsley

Enjoy the beauty of the North York Moors National Park and the Howardian Hills National Landscape from the comfort of Ryedale Cottage. The pretty stone cottage is one of four at Sproxton Hall Cottages, just two miles from Helmsley. There is space for four guests to sleep in two bedrooms, making it perfect for couples and families who want a peaceful location that is close to some of the region's favourite attractions such as Helmsley Castle, Pickering steam railway, Castle Howard, York, Whitby and Herriot Country. Ryedale Cottage is single-storey and has floor to ceiling windows in the living area, old beams and historic stonework. A log burner makes for a cosy stay.

Bilsdale Cottage is a hidden gem on the edge of the North York Moors National Park and within the Howardian Hills National Landscape. This historic stone cottage, which is one of four at Sproxton Hall Cottages, is set back from a private road on the edge of a quiet hamlet, only two miles south of the tourist friendly market town of Helmsley.  With space to sleep four people in two bedrooms, Bilsdale Cottage is ideal for families and couples. The cottage welcomes 3 dogs and has its own enclosed garden. Dogs can also enjoy the onsite dog exercise paddock and the bridleway at the end of the drive. Guests can wake up to beautiful far reaching views, knowing that their day is full of spectacular scenery and memorable experiences which could include walking around the ancient city walls of York, savouring the splendour or Castle Howard, strolling by the seaside at Whitby or feeling nostalgic in Herriot Country. Helmsley and its surrounding villages has a growing reputation for high quality restaurants, as well as plenty of traditional dog friendly country pubs.

Set back from a quiet road in the peaceful village of Harome, Overdale Cottage is close to the border of the North York Moors National Park and within easy reach of Helmsley, Pickering and York. The pet-friendly cottage has recently been refurbished to offer very comfortable accommodation for couples and families. There is space for four people to stay in two bedrooms, and pets are welcome. The cottage has lovely views of the surrounding countryside and is close to fantastic walks and cycle trails. There are even two excellent pubs within walking distance - the Star Inn and the Michelin-starred Pheasant, or stay in for dinner and enjoy a glass of wine in front of the open fire.

Spacious and full of character, this welcoming holiday retreat for two sits on a small dales hill farm in the North York Moors National Park. Low Crossett Cottage offers the opportunity of peace and tranquility, lovely walks, spectacular views and a comfy self-catering base for exploring the areas many attractions.

A cosy welcoming holiday cottage with immense character, ideally placed on the edge of the North York Moors in the popular market town of Helmsley with its castle and superb walks, shops, pubs and restaurants on the doorstep. Offering a high standard of dog-friendly self-catering accommodation all year round.

Old Bald Peg is a cottage with a pedigree as impressive as its Thoroughbred namesake. The Victorian terraced former estate cottage has been refurbished to provide a charming holiday home sleeping four guests in two bedrooms, with two well-behaved dogs welcome by prior arrangement. Situated in the quiet village of Wass, in the North York Moors National Park, within an easy stroll of two great gastropubs and the ancient ruins of Byland Abbey and close to the market towns of Helmsley, Thirsk and the historic city of York. Other local attractions include Rievaulx Abbey, Castle Howard, Sutton Bank and the Kilburn White Horse. Explore the Cleveland Way, the North Yorkshire Heritage Coast and the wild beauty of the moors.

Welcome to The Helmsley Retreat Nestled in the picturesque market town of Helmsley, The Helmsley Retreat is the perfect base for exploring North Yorkshire. This charming cottage offers modern comforts, including a private hot tub and sauna, ensuring a relaxing and memorable stay. Just a short walk from the vibrant market square with its independent shops, pubs, and cafes, the cottage combines convenience with tranquility. Ideal for couples or small families, The Helmsley Retreat provides the perfect blend of comfort, charm, and adventure.

"Rising Sun" is a 1 bed holiday Lodge sleeping up to 2 guests in York. With Helmsley and Pickering just across the North York Moors National Park, Kirkbymoorside is a lovely historic market town. It's a wonderful spot, bursting with quintessential Yorkshire charm, and the hub of all the surrounding farms and...

"Peg's Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. On the southern edge of the North York Moors National Park is the prestigious market town of Helmsley. Lying in a sheltered corner of Upper Ryedale, this lovely settlement boasts a spacious market square surrounded by houses, hotels and shops...

"Foxglove Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Beadlam is a lovely village situated in the Ryedale district of North Yorkshire, resting on the edge of the North York Moors National Park, home to a farm shop and tea room, a local pub and a fish and chip shop. Helmsley market town is nearby...

"1 Bed Cottage in Kirkbymoorside" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 bedroom - king-size - 1 En-suite shower and WC - Electric induction hob, two microwaves and fridge - Parking for 1 car - Pub and shop...

"Chapel Cottage" is a 2 bed holiday Cottage sleeping up to 3 guests in York. The small, pretty village of Stillington is situated between York and Helmsley and has a Post Office/shop, pubs, Indian restaurant, fish and chip shop and antiques showroom. From the village, footpaths and bridleways lead to the surrounding...

"1 Bed Cottage in Kirkbymoorside" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Additional information and rules. Please enquire if you wish to bring more than 1 dog - 1 bedroom: super-king-size bed - 1 bathroom: freestanding bath, walk-in shower, WC - Electric oven and hob, dishwasher, fridge/freezer,...

"2 Bed Cottage in York" is a 2 bed holiday Cottage sleeping up to 2 guests in York. Additional information and rules. Please enquire if you wish to bring more than 1 dog - Sleeps 2 + 1 - 2 bedrooms – 1 super-king-size and 1 single - 1 shower room with shower and WC - Electric oven and hob, microwave, fridge...

"Beacon Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. This historic market town, with its full range of amenities and traditional shops, cafes, pubs and restaurants, serves as the official gateway to the beautiful North York Moors National Park, home of the Heartbeat countryside. Enjoy a ride on...

"Black Eagle Cottage, Harome" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Step inside to discover a spacious couples retreat where a stunning vaulted ceiling creates a light and airy atmosphere. The inviting sitting room has a comfortable sofa, making it an idyllic spot to curl up after a day exploring the moors. The...

"Keldy Golden Oak Hideaway" is a 1 bed holiday Lodge sleeping up to 2 guests in North Yorkshire. Nestled within the enchanting woodlands of Keldy, the Golden Oak Hideaway offers an idyllic retreat on the edge of the breathtaking North York Moors National Park. This serene area is a nature lover's paradise, where the whisper of the trees...

"Elm Tree Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. The sleepy little rural village of Dalton, four miles from Thirsk, sits in a perfect touring location for discovering North Yorkshire. With the gateway to the North York Moors National Park to the east and Yorkshire Dales National Park to the...

"The Stables, Crayke Lodge" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Easingwold is a small, historic market town situated close to the city of York. The town centre boasts a large market square surrounded by splendid Georgian buildings and there are a good selection of shops, pubs and cafes on offer. York,...

"The Bothy, 21 West Street" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. The market town of Malton has a weekly market, a range of amenities and a cinema. The Yorkshire Moors are to the north, and the Yorkshire Wolds are to the south, perfect for walkers and cyclists. The coastline is 24 miles away with Scarborough,...

"Castle Lodge - UK50987" is a 1 bed holiday Cottage sleeping up to 2 guests in York. A cosy, pet friendly lodge for an off grid escape for two in the shadow of Sheriff Hutton Castle and a short walk from the village centre and local pub.. 1 step to entrance. All on the Ground Floor: Open plan living...

"Bluebell - UK51767" is a 1 bed holiday Apartment sleeping up to 2 guests in North Yorkshire. Bluebell at Stape Head Farm is a beautifully converted stone barn, all on one level, offering a peaceful and authentic rural escape in the heart of the North York Moors National Park.. 1 step to entrance. All on the Ground Floor:...

"The Rams Rest - UK48823" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. Hand crafted on site by the owner this shepherds hut is unique, thoughtfully designed and really cosy. Ideally placed to explore the North Yorkshire Moors National Park and historic York.. 3 steps to entrance. All on the Ground Floor:...

"Wren Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. A charming detached cottage in a beautiful setting, a perfect romantic retreat.. 2 steps to entrance. All on the Ground Floor: Living/dining room: 32" Freeview TV, Woodburner Kitchen:...

"Blacksmiths Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Blacksmiths Cottage is an ideal base for walking, touring and relaxing anytime of the year.. All on the Ground Floor: Open plan living space. Living area: Freeview TV,...

"Ewe Lodge - UK48824" is a 1 bed holiday Apartment sleeping up to 2 guests in North Yorkshire. Great location for exploring the North Yorkshire Moors National Park and Dalby Forest. This is a gem for a romantic break away.. 3 steps to entrance. All on the Ground Floor: Open plan living...

"The Granary - UK45696" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. This beautifully furnished barn conversion is nestled in the North York Moors National Park, in a quaint rural village.. 1 step to entrance. All on the Ground Floor: Open plan living space. Living...

"Hindburn" is a 1 bed holiday Cottage sleeping up to 2 guests in North Yorkshire. With 42 acres of landscaped natural and wooded areas surrounding the property this is the ideal romantic retreat.. All on the Ground Floor: Open plan living space. Living area: Freeview TV,...

"Ash Lodge" is a 1 bed holiday Lodge sleeping up to 2 guests in York. New for 2022. Fabulous one bedroom lodge with super king-size bed. en suite shower room. Private south facing decking area with large hot tub.. Nestling in a secluded peaceful setting, these stunning lodges are surrounded by the beautiful open...

"Grosmont Lodge" is a 1 bed holiday Lodge sleeping up to 2 guests in North Yorkshire. Luxury lodge with one double, ideal for couples. Bath with overhead shower. Stylish living area with verandah overlooking the lake. Outdoor hot tub. No pets.. Pickering Lodges is part of our Evermore Lodge Holidays Collection, a luxurious haven...

"Thornton Le Dale Lodge" is a 1 bed holiday Lodge sleeping up to 2 guests in North Yorkshire. Luxury lodge with open plan bedroom with king-size double and roll top bath with overhead shower. Stylish open-plan living area with verandah overlooking lake. Outdoor hot tub. No pets.. Pickering Lodges is part of our Evermore Lodge Holidays...