Cottages in Helmsley

REFINE SEARCH

Your search returned 98 cottages.

All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

View on map
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • tripadvisor rating Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon half
    • Sleeps3
    • Bedrooms1
    • PetsNo

    Delightful conversion of old cow byre in centre of Wrelton. Exposed timbers, wooden floors. Quality cottage, very high standard. Excellent walking and touring base. Pickering 3 miles. (Ref. 1577)

    7 nights from £241

    Book Now
  • 1 / 10
    • Cow Byre Cottage - 1577 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • tripadvisor rating Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full
    • Sleeps4
    • Bedrooms2
    • PetsYes

    Delightful stone cottage in courtyard, set in open countryside. Character, quality accommodation. Oak floors, exposed beams. Kirkbymoorside 1.5 miles, Pickering 6 miles. (Ref. 929319)

    Last booked 2 hours ago

    7 nights from £296

    Book Now
  • 1 / 12
    • Grouse Cottage - 929319 - photo 1
    • Sykes Cottages Rating Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon Tourist Board ratings icon
    • Sleeps2
    • Bedrooms1
    • PetsNo

    A charming barn conversion located near the village of Thirsk, North Yorkshire. Breakfast bar. Open-plan. High ceilings. Ripon 11 miles; York 23 miles. (Ref. 19934)

    7 nights from £221

    Book Now
  • 1 / 16
    • Kitchen Cottage - 19934 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • Sleeps6
    • Bedrooms3
    • PetsYes

    Country detached cottage located in the village of Lastingham. Woodburning stove and piano. Countryside views. Kirkbymoorside 5.3 miles. (Ref. 947541)

    7 nights from £399

    Book Now
  • 1 / 18
    • The Green - 947541 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • Sleeps5
    • Bedrooms3
    • PetsYes

    Charming, stone, period cottage in pretty village of Hutton-le-Hole. Open fire, cosy, comfortable accommodation. Private rear garden, lovely views over village green. Walkers' delight. Kirkbymoorside 3.5 miles. (Ref. 22745)

    7 nights from £384

    Book Now
  • 1 / 9
    • Brookleigh - 22745 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • tripadvisor rating Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full
    • Sleeps4
    • Bedrooms2
    • PetsNo

    Wonderful, semi-detached, barn conversion near Thirsk. Eco-friendly central heating. WiFi. Open plan living area. Ideal touring location. Thirsk 4 miles. (Ref. 15032)

    Last booked yesterday

    7 nights from £271

    Book Now
  • 1 / 12
    • Calf House - 15032 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • Sleeps4
    • Bedrooms2
    • PetsNo

    A stunning ground floor barn conversion five miles from Malton in North Yorkshire. Open-plan living. En-suites. Countryside views. Near North York Moors National Park. (Ref. 943576)

    7 nights from £347

    Book Now
  • 1 / 24
    • Cow Byre - 943576 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • tripadvisor rating Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full
    • Sleeps8
    • Bedrooms4
    • PetsYes

    Superb stone-built semi-detached house with wonderful views over Rosedale Valley. Character accommodation, open fire, picture window, conservatory. Pickering 10 miles. (Ref. 1438)

    7 nights from £426

    Book Now
  • 1 / 24
    • Woodlea - 1438 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • Sleeps4
    • Bedrooms2
    • PetsNo

    Ideal for a family holiday in the heart of market town. Front garden and rear courtyard. WiFi. Thirsk 14 miles. (Ref. 956799)

    7 nights from £462

    Book Now
  • 1 / 11
    • 8 Pottergate Mews - 956799 - photo 1
    • Sykes Cottages Rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes
    • tripadvisor rating Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full Trip Advisor rating icon full
    • Sleeps2
    • Bedrooms1
    • PetsNo

    Charming semi-detached Kirkbymoorside cottage set in a popular town. Traditionally furnished. Ideal area for walking and exploring the North York Moors. Pickering 6 miles. (Ref. 8501)

    7 nights from £239

    Book Now
  • 1 / 8
    • Pound Cottage - 8501 - photo 1
View on map
All cottages available for only £20 Deposit!*

For a limited time only, all our cottages can be reserved for only £20 Deposit. Don't miss out!

*Applicable to holidays commencing at least 6 weeks in the future. Full balance due 6 weeks prior to departure. Please refer to Book Now Pay Later Terms and Conditions for further information.

Just show me Helmsley Cottages

Please find below a selection of self catering holiday cottages to rent in Helmsley, Yorkshire.

On the borders of the North York Moors National Park, this lovely little market town is a haven for walkers as it's the starting point of the Ebor Way, a long distance trail that connects the Cleveland Way and Dales Way.

Of course, the National Park is a playground for all kinds of other outdoor activities too like cycling, horse riding, fishing and golf. Plus it's only a short distance from our Helmsley cottages to the coast if you fancy a day on the beach.

Fresh air and exercise create healthy appetites and Helmsley's pubs, tearooms and restaurants are extremely inviting - worth a mention is the Black Swan for fine food amid swish surroundings. There are also stylish shops selling everything from gifts and crafts to country wear, along with a weekly street market.

Attractions include the beautiful Parish Church, a thriving Arts Centre and Helmsley Castle, a magnificent ruined Norman keep overlooking the town, with displays of archaeological treasures and a fascinating interactive exhibition. In the shadow of the castle, just a short distance from the town centre, lies the estate of Duncombe Park and its National Nature Reserve. Spend a day here admiring ancient trees and colourful birdlife and look out for the five-acre Helmsley Walled Garden, a working kitchen garden brimming with special collections of Yorkshire apple trees, Victorian vines and numerous varieties of clematis.

And don't miss a trip to Rievaulx Abbey, an amazing Gothic ruin just a couple of miles away; or Nunnington Hall, a stunning 17th Century manor house.

Sounds appealing? Then book a Helmsley cottage.