Self Catering Holiday Cottages in Helmsley

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.

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.

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.

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.

"Peep o' Day" is a 1 bed holiday Lodge sleeping up to 2 guests in York. North York Moors National Park borders Kirkbymoorside, a beautiful old market town located between Helmsley and Pickering. Located in the heart of the countryside, it exudes a distinct sense of place that can only be found in a site like this...

"Westfield Lodge" is a 1 bed holiday Lodge sleeping up to 2 guests in York. The tranquil village of Sheriff Hutton is nestled among gently sloping hills between York and Malton. The village is charming, with a green and two pubs that serve meals, one of which dates back to the 1600s. The North York Moors Steam Railway...

"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...

"Cartwheel Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Yearsley is a delightful small village resting in North Yorkshire, in the heart of the Howardian Hills aonb. Yearlsey is near to the village of Ampleforth where you can find the nearest amenities including a village shop and a pub, with more...

"Daisy cottage" is a 3 bed holiday Cottage sleeping up to 5 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...

"12 Castlegate" 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...

"Ghyll Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Perfectly positioned for touring both the Moors and the Coast, the picturesque village of Rosedale Abbey is situated in the heart of the North York Moors National Park. Located in Rosedale, a beautiful valley of sweeping hillsides and...

"Ducky's" is a 3 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. This old market town, with its complete variety of services and traditional shops, cafes, pubs, and restaurants, serves as the official entry to the stunning North York Moors National Park, where the Heartbeat landscape is located. Enjoy a ride...

"Sheep Cote Shepherds Hut" is a 1 bed holiday Lodge sleeping up to 2 guests in Middlesbrough. Stokesley is an attractive, elegant, historic market town which was mentioned in the Domesday Book of 1086, with many interesting Georgian and Victorian buildings. The River Leven flows through the town and is crossed by the ancient Pack Horse...

"Sixpence 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...

"Brewers Cottage" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Middleton is a small, rural village settled between the market towns of Kirkbymoorside and Pickering in Ryedale. The village rests just south of the North York Moors National Park, meaning a wealth of walks and cycling routes are just a stone's...

"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 Old Post Office" is a 5 bed holiday Cottage sleeping up to 10 guests in York. The unspoiled village of Ampleforth, which is home to a few old homes, two pubs, a tearoom, and the neighbourhood store, is situated on the edge of the North York Moors National Park. There are several excellent restaurants nearby, and the...

"The Green, Castle Howard, Coneysthorpe" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. This delightful 18th Century stone cottage brings you a beguiling mix of contemporary comforts with timeless elegance, thanks to carefully-chosen modern fixtures and fittings that blend perfectly with period furniture taken from Castle Howard...

"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 - Ornate wrought iron double high bed - 1 bathroom - Electric oven and hob, microwave, dishwasher, washing machine and fridge/freezer - Wood...

"Holly Cottage" is a 3 bed holiday Cottage sleeping up to 6 guests in York. A small characteristic village in the Ryedale district of North Yorkshire, Beadlam is unusual in that it is directly joined onto another village, Nawton, together commonly known as Nawton Beadlam. The village offers a pub serving food and a...

"Rose Lodge" is a 3 bed holiday Lodge sleeping up to 6 guests in York. Sheriff Hutton is a small village resting between the hills of York and Malton. The village is steeped with history, with ruins of a 14th century castle, housing Richard III in 1483, and a medieval church with Norman tower dating from 1100....

"2 Bed Cottage in Pickering" is a 2 bed holiday Cottage sleeping up to 4 guests in North Yorkshire. Additional information and rulesNo dogs allowed - 2 bedrooms – 1 king-size, 1 twin zip-and-link (can be a super-king-size on request) - 1 family bathroom with a shower over bath and WC - Electric oven and hob,...

"Webstone House" is a 3 bed holiday Cottage sleeping up to 6 guests in North Yorkshire. Osmotherley is a picturesque village, tucked inside the North York Moors National Park, nestled between the Cleveland Hills and the Yorkshire Dales. Osmotherley is very popular with cyclists and walkers, with the Cleveland Way, the Coast to...

"Ghyll Crest" is a 6 bed holiday Cottage sleeping up to 12 guests in North Yorkshire. Osmotherley is a picturesque North Yorkshire conservation village, with grass and tree lined streets set on a small hillside on the western edge of the North York Moors National Park, nestling between the Cleveland Hills to the east and the...

"Providence Court" is a 1 bed holiday Cottage sleeping up to 2 guests in York. This small, historic market town lies within the Vale of York between the City and the Hambleton Hills, on the edge of the North York Moors National Park. Picturesque and peaceful, it is a perfect introduction to Herriot Country. The town's...

"St Gregory’s Cottage" is a 1 bed holiday Cottage sleeping up to 2 guests in York. Lying in a sheltered corner of Upper Ryedale, on the southern edge of the North York Moors National Park, Helmsley is a prestigious market town with a spacious market square surrounded by houses, hotels and shops. The area is important...

"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...

"Station View" is a 1 bed holiday Apartment sleeping up to 2 guests in North Yorkshire. The market town of Pickering, with its range of amenities and traditional shops, cafes, pubs and restaurants, serves as the official gateway to the North York Moors National Park. The Beck Isle Museum is certainly worth a visit and walkers can...