Holiday rentals in Helmsley
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Top-rated holiday rentals in Helmsley
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Popular amenities for Helmsley holiday rentals
Other great holiday rentals in Helmsley
Tiny home in Newton-on-Rawcliffe
4.98 out of 5 average rating, 196 reviewsThe Hide NYM National Park Cosy Cabin with hot tub
Apartment in North Yorkshire
4.98 out of 5 average rating, 224 reviews2 Chiltern Place Malton-Stylish boutique apartment
Barn in Aislaby, Pickering
4.97 out of 5 average rating, 234 reviewsStunning views, 4 acres, dog friendly, Yorkshire
Home in Kirkbymoorside
4.9 out of 5 average rating, 303 reviewsOakforge Cottage, a spacious home from home.
Cottage in North Yorkshire
4.9 out of 5 average rating, 206 reviewsCosy character cottage in heart of Pickering
Cottage in Bewerley
5.0 out of 5 average rating, 285 reviewsThe End Place - A romantic hideaway for two
Cottage in Sessay
4.95 out of 5 average rating, 226 reviewsThe Cobbler's Cottage
Cottage in North Yorkshire
4.87 out of 5 average rating, 83 reviewsLuxury Old Stone Cottage, Beautifully Presented
Quick stats about holiday rentals in Helmsley
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.7K reviews
Nightly prices starting at
£55 before taxes and fees
Your guide to Helmsley
Welcome to Helmsley
Nestled amid the 554 square miles of the North York Moors National Park, Helmsley — located on the banks of the River Rye — is the quintessential English market town, boasting cobbled market squares, honeyed-stone cottages, historic inns, and 51 listed buildings, all looked over by the ancient ruins of the 12th-century Helmsley Castle. Circled by the most wondrous countryside, Helmsley really is the perfect place to base yourself as you explore the glories of the surrounding landscape: Two of the finest trails in the United Kingdom, The Cleveland Way and the Ebor Way, both start in the town. The town comes to life on market day (Friday), when hundreds of independent traders descend to peddle their wares. But if the hustle and bustle gets to be too much, there’s also a heated outdoor community pool to enjoy in the summer months.
The best time to stay in a holiday rental in Helmsley
There really isn’t a bad time to visit the North York Moors. During summer and early autumn, the area’s famous heather moorland is at its most spectacular, and a good reason to plan some extended walking trips. Though always pack plenty of layers and waterproofs, as the weather can change instantly in this part of the world. Also in late summer, the World Jam Festival descends on Helmsley, involving tea duelling, costume competitions, and lots of delicious jam. The town was also recently voted one of the best places in the United Kingdom to spend Christmas break, with all the independent shops attempting to exude as much seasonal cheer as possible. So if you’re looking for somewhere different to spend the holiday season, then Helmsley is sure to get you feeling festive.
Top things to do in Helmsley
Helmsley Castle
First built around 1120, this castle has lived many lives. Initially designed as a defensive fortress, it became an elaborate Tudor mansion, then a Civil War stronghold, and later a romantic Victorian ruin. Now you can enjoy a hands-on exhibition illustrating its many guises and an audio tour of the site. Beside the castle is Helmsley Walled Garden, a beautifully restored 18th-century garden that is an oasis of tranquility.
Rievaulx Abbey
Just a couple of miles from Helmsley Castle (there’s a trail taking you on a scenic route from one site to the other) are more impressive ruins, though of a more ecclesiastical nature. Rievaulx Abbey was once one of England’s most powerful Cistercian monasteries before being dissolved by Henry VIII in 1538. A detailed audio tour highlights the fascinating history of this very special place.
Nunnington Hall
One of the finest manor houses in the United Kingdom is only 6 miles southeast of Helmsley. Erected in the 17th century and now maintained by the National Trust, Nunnington Hall features a delightful walled garden where peacocks stroll. As well as the wonderful period rooms and an astonishing collection of miniature rooms, the Hall also stages contemporary art and photography exhibitions.
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