Helmsley Holiday Cottages

Helmsley Holiday Cottages

Home to the biggest range at the lowest price

Check-in

{{checkInFormatted}}

Add dates

± {{flex}}
Check-out

{{checkOutFormatted}}

Add dates

± {{flex}}

Live availability

Live prices

Book instantly

Did you know? We have a dedicated site just for pet friendly holidays, take me to Dog Friendly Cottages >

Helmsley Cottages

  • Last Minute Cottages - 2 Bed Cottage in Helmsley
  • 2

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S228921

    2
    4
    Additional information and rules - 2 bedrooms – 1 king-size and1 double sofa bed in the second lounge - 1 bathroom with shower over bath and WC - 1 wet room - Kitchen with oven, hob, dishwasher, washer/dryer, microwave and fridge with small...

    From

    £94

    per night
    View

  • Last Minute Cottages - 3 Bed Cottage in Helmsley
  • North Yorkshire

    3 Bed Cottage in Helmsley

    Ref: S230806

    3
    6
    Additional information and rules No dogs allowed - 3 bedrooms - 1 super-king-size (can also be made up as a twin on request), 1 double and 1 twin - 3 bathrooms - 2 en-suite shower rooms with WC, 1 bathroom with Jacuzzi bath, plus 1 additional...

    From

    £131

    per night
    View

  • Last Minute Cottages - 4 Bed Cottage in Helmsley
  • 2

    North Yorkshire

    4 Bed Cottage in Helmsley

    Ref: S1296222

    4
    8
    Additional information and rules - 4 bedrooms – 3 super-king-size, 1 bunk bed - 3 bathrooms – 2 en-suite bathrooms with bath, walk-in shower and WC, 1 en-suite shower room with walk-in shower and WC, plus 1 additional WC - Induction hob,...

    From

    £227

    per night
    View

  • Last Minute Cottages - 2 Bed Cottage in Helmsley
  • 1

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S230564

    2
    3
    Additional information and rules - 2 bedrooms: 1 king-size bed, 1 single bedroom - 1 bathroom: wet room with walk-in shower and WC - Semi-detached property - Wood burner - Heated flooring - Welcome hamper upon arrival - Oven and hob,...

    From

    £94

    per night
    View

  • Last Minute Cottages - Ivy Cottage
  • North Yorkshire

    Ivy Cottage

    Ref: S75218

    Reviews 35

    3
    5
    Situated 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. There is excellent walking on the doorstep, the Cleveland Way starts...

    Check for price

    View
    Partner deal

  • Last Minute Cottages - Rosebeck
  • 3

    North Yorkshire

    Rosebeck

    Ref: S1013079

    2
    4
    Rosebeck, a property with a garden, is set in Helmsley, 39 km from York Minster, 39 km from York Railway station, as well as 39 km from York Train Station. The 4-star holiday home is 34 km from Dalby Forest. The property is non-smoking and is...

    From

    £82

    per night
    View
    Partner deal

  • Last Minute Cottages - The Annex - central Helmsley with parking
  • 3

    North Yorkshire

    The Annex - central Helmsley with parking

    Ref: S523226

    2
    4
    Situated 24 km from Flamingo Land Theme Park, The Annex - central Helmsley with parking features accommodation with free WiFi and free private parking. The property is around 38 km from York Minster, 39 km from York Railway station and 39 km from...

    From

    £156

    per night
    View
    Partner deal

  • Last Minute Cottages - The Old Post Office - Central Helmsley with Parking
  • North Yorkshire

    The Old Post Office - Central Helmsley with Parking

    Ref: S519372

    2
    6
    The Old Post Office - Central Helmsley with Parking in Helmsley provides accommodation with free WiFi, 24 km from Flamingo Land Theme Park, 34 km from Dalby Forest and 38 km from York Minster. The property is around 39 km from York Train Station,...

    From

    £143

    per night
    View
    Partner deal

  • Last Minute Cottages - The Nest
  • 3

    North Yorkshire

    The Nest

    Ref: S601027

    1
    2
    The Nest, a property with a garden, is set in Helmsley, 38 km from York Minster, 39 km from York Railway station, as well as 39 km from York Train Station. Featuring free private parking, the 4-star holiday home is 24 km from Flamingo Land Theme...

    From

    £56

    per night
    View
    Partner deal

  • Last Minute Cottages - Rye Court Cottage and Annex Central Hemsley
  • 3

    North Yorkshire

    Rye Court Cottage and Annex Central Hemsley

    Ref: S524778

    5
    13
    Rye Court Cottage and Annex Central Hemsley, a property with a garden and a terrace, is located in Helmsley, 34 km from Dalby Forest, 38 km from York Minster, as well as 39 km from York Railway station. This property offers access to a patio, free...

    From

    £447

    per night
    View
    Partner deal

  • Last Minute Cottages - Riccal Dale Cottage
  • 3

    North Yorkshire

    Riccal Dale Cottage

    Ref: S323146

    2
    4
    Set in Helmsley in the North Yorkshire region and Flamingo Land Theme Park reachable within 27 km, Riccal Dale Cottage offers accommodation with free WiFi, barbecue facilities, a garden and free private parking. The property is around 37 km from...

    Check for price

    View
    Partner deal

  • Last Minute Cottages - Toad Hall
  • North Yorkshire

    Toad Hall

    Ref: S385511

    2
    4
    Toad Hall, a property with a garden, is located in Helmsley, 34 km from Dalby Forest, 38 km from York Minster, as well as 39 km from York Railway station. The property is situated 39 km from York Train Station, 47 km from Lightwater Valley Theme...

    Check for price

    View
    Partner deal

  • Last Minute Cottages - Bilsdale Cottage
  • 3

    North Yorkshire

    Bilsdale Cottage

    Ref: S323151

    2
    4
    Set in Helmsley in the North Yorkshire region and Flamingo Land Theme Park reachable within 27 km, Bilsdale Cottage offers accommodation with free WiFi, barbecue facilities, a garden and free private parking. The property is around 37 km from...

    Check for price

    View
    Partner deal

  • Last Minute Cottages - Kirkdale Cottage
  • 3

    North Yorkshire

    Kirkdale Cottage

    Ref: S323150

    3
    5
    Set in Helmsley in the North Yorkshire region and Flamingo Land Theme Park reachable within 27 km, Kirkdale Cottage offers accommodation with free WiFi, barbecue facilities, a garden and free private parking. The property is situated 37 km from...

    Check for price

    View

  • Last Minute Cottages - Fox Cottage
  • 2

    North Yorkshire

    Fox Cottage

    Ref: S1028684

    2
    4
    Fox Cottage is a dog-friendly holiday cottage sleeping up to four guests in the North Yorkshire market town of Helmsley with a good choice of amenities including eating establishments on the doorstep. Undergoing substantial refurbishment in early...

    From

    £71

    per night
    View

  • Last Minute Cottages - 3 Bed Cottage in Helmsley
  • 2

    North Yorkshire

    3 Bed Cottage in Helmsley

    Ref: S366423

    3
    4
    Additional information and rules - Sleeps 4 + 1 - 3 bedrooms – 1 double, 1 twin and 1 single - 1 shower room with shower and WC - Electric range-style oven and gas hob, microwave, fridge/freezer and dishwasher, please note there is no washing...

    From

    £88

    per night
    View

  • Last Minute Cottages - 3 Bed Cottage in Helmsley
  • 1

    North Yorkshire

    3 Bed Cottage in Helmsley

    Ref: S1294750

    3
    6
    Additional information and rules - 3 bedrooms – 1 double, 2 king -size - 3 bathrooms – 1 en-suite wet room with shower, 2 en-suites with baths and showers over - 1 separate WC - Electric oven, induction hob, microwave, fridge, freezer and...

    From

    £129

    per night
    View

  • Last Minute Cottages - 4 Bed Cottage in Helmsley
  • 2

    North Yorkshire

    4 Bed Cottage in Helmsley

    Ref: S1292607

    4
    8
    Additional information and rules - 4 bedrooms – 1 king-size, 1 queen-size, 2 twins - 3 bathrooms – 1 shower room with walk-in shower and WC, 2 en-suite bathrooms with bath and WC, plus additional ground-floor WC - AGA, induction hob,...

    From

    £231

    per night
    View

  • Last Minute Cottages - 1 Bed Cottage in Helmsley
  • North Yorkshire

    1 Bed Cottage in Helmsley

    Ref: S1297449

    1
    2
    Additional information and rules No dogs allowed - 1 king-size bedroom - 1 en-suite shower room with WC - Electric hob/oven, fridge and dishwasher - Smart TV in living space - Wood burner in living space (starter pack of logs...

    From

    £96

    per night
    View

  • Last Minute Cottages - 2 Bed Cottage in Helmsley
  • 2

    North Yorkshire

    2 Bed Cottage in Helmsley

    Ref: S777440

    2
    4
    Additional information and rules - 2 bedrooms - 1 king-size, 1 twin (400TC Egyptian cotton) - 3 bathrooms - 1 en-suite with shower and WC, 1 en-suite with shower over bath and WC, 1 downstairs walk-in shower and WC - Electric range cooker with...

    From

    £156

    per night
    View
    Partner deal

  • Last Minute Cottages - Bridge House
  • North Yorkshire

    Bridge House

    Ref: S377695

    2
    4
    Offering a garden and river view, Bridge House is situated in Helmsley, 38 km from York Minster and 39 km from York Railway Station. Providing free private parking, the 5-star holiday home is 24 km from Flamingo Land Theme Park. The property is...

    Check for price

    View
    Partner deal

  • Last Minute Cottages - The Cart House
  • 3

    North Yorkshire

    The Cart House

    Ref: S417838

    3
    6
    The Cart House, a property with a garden, is situated in Helmsley, 38 km from York Minster, 39 km from York Railway station, as well as 39 km from York Train Station. Providing free private parking, the 4-star holiday home is 24 km from Flamingo...

    From

    £132

    per night
    View
    Partner deal

  • Last Minute Cottages - Holly-Garth
  • 3

    North Yorkshire

    Holly-Garth

    Ref: S1016725

    4
    8
    Holly-Garth, a property with a garden, is located in Helmsley, 38 km from York Minster, 39 km from York Railway station, as well as 39 km from York Train Station. Featuring free private parking, the 4-star holiday home is 24 km from Flamingo Land...

    From

    £116

    per night
    View
    Partner deal

  • Last Minute Cottages - Borough Beck Cottage
  • 3

    North Yorkshire

    Borough Beck Cottage

    Ref: S419751

    3
    5
    Borough Beck Cottage, a property with a garden, is located in Helmsley, 39 km from York Minster, 39 km from York Railway station, as well as 39 km from York Train Station. The 4-star holiday home is 34 km from Dalby Forest. The property is...

    From

    £135

    per night
    View
    Showing 1 - 24 of 28 properties

    Helmsley Holiday cottages

    Nestled in the heart of Ryedale, on the edge of the North Yorkshire Moors, is the pretty market town of Helmsley. A historic settlement with a Norman castle at its centre, Helmsley is well worth a visit for its medieval charm. Take a walk around the town walls, explore the local shops and stop for a bite to eat in one of the many quaint cafés.

    If you’re looking for somewhere to stay on your break, holiday cottages in Helmsley are the perfect option. With plenty of space for everyone, choose from large houses with private gardens, cosy cottages with open fires, or modern dwellings with stunning views.

    Holiday cottages in Helmsley can be booked through Snaptrip, with our best price guarantee ensuring you get the best deal on your break. With thousands of properties to choose from throughout the UK, we’ve got something to suit everyone. With our best price guarantee, you're sure to be getting the best deal on your holiday cottage. If you need a little extra hand finding the perfect holiday cottage, our friendly customer service team can help you find the perfect property - complete with hot tubs, private gardens and more.

    Other places to visit

    If you’re staying in Helmsley, why not explore some of these nearby towns and villages:

    Read more > less >

    Best price guarantee

    No one can beat our prices

    Best price guarantee

    Our cottages are professionally managed by our partners and payments are taken by them, but rest assured, by booking via Snaptrip you'll pay the lowest possible price for your trip.

    We never charge you more than you would pay booking directly on the partner's site and if you become a member you can save even more. If you find a property priced lower anywhere else on the internet (we’d be amazed if you do), simply email us at marketing@snaptrip.com and we'll refund you the difference.

    We bring it all together

    Biggest range of self-catering holiday properties

    We connect you to a range of great suppliers with a huge selection of properties. We've done the research, so that you don't have to.

    View properties >

    We get you
    the lowest price

    We help you to complete your booking whilst giving you discounts, member only prices and our best price guarantee.

    A marketplace
    you can trust

    We connect you with the best professionally managed properties and our marketing leading customer services can help you every step of the way.

    Start your journey >

    Join for free to get access to exclusive prices on thousands of properties.

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    Sign up to see

    Login to see

    • Discounts exclusive to members
    • Save & share your favourite properties
    • See your previously viewed properties

    Did you mean {{ suggestedEmail }}?

    or

    Already a member login here

    Not a member?

    By entering my email address, I agree to Snaptrip's Terms of service, Privacy policy and to receive email updates, news, & offers from Snaptrip.

    Welcome, member discounts are now available.