Hot Tub
Luxury
Wifi
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
£1,885
Helmsley Cottages
This charming market town nestled in the rolling hills of North Yorkshire, offers a perfect blend of history, culture, and natural beauty. With its picturesque streets lined with historic buildings, quaint shops, and welcoming cafes, it's the ideal destination for a leisurely retreat. Whether you're exploring the imposing ruins of Helmsley Castle, strolling through the peaceful grounds of Duncombe Park, or indulging in a spot of retail therapy at the town's boutique shops, there's something for everyone to enjoy. Plus, with its proximity to the stunning North York Moors National Park, outdoor enthusiasts can take advantage of the numerous walking trails and scenic viewpoints nearby. And don't forget to sample some local delicacies at one of Helmsley's charming eateries before you leave. Looking for your next home away from home, then search our selection of Helmsley cottages for inspiration.
Popular Helmsley Cottages
Car parking on site
Garden / Patio
- Sleeps up to 3
- 1 bedroom
- 1 bathroom
- Up to 0 pets allowed
5
out of 5
7 nights
From
£325
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 8
- 4 bedrooms
- 3 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£679
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
4.7
out of 5
7 nights
From
£689
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
£895
Wifi
Car parking on site
Detached
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£565
Hot Tub
Luxury
Wifi
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.6
out of 5
7 nights
From
£649
Wifi
Car parking on site
Garden / Patio
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
4.4
out of 5
7 nights
From
£289
Hot Tub
Luxury
Wifi
- Sleeps up to 8
- 4 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
£2,015
Dog Friendly Helmsley Cottages
Hot Tub
Luxury
Wifi
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
£1,885
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 8
- 4 bedrooms
- 3 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£679
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
£895
Wifi
Car parking on site
Detached
- Sleeps up to 4
- 2 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
4.8
out of 5
7 nights
From
£565
Hot Tub
Luxury
Wifi
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.6
out of 5
7 nights
From
£649
Wifi
Car parking on site
Garden / Patio
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
4.4
out of 5
7 nights
From
£289
Hot Tub
Luxury
Wifi
- Sleeps up to 8
- 4 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
£2,015
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£685
Luxury Helmsley Cottages
Hot Tub
Luxury
Wifi
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
£1,885
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
£895
Hot Tub
Luxury
Wifi
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 2 pets allowed
4.6
out of 5
7 nights
From
£649
Hot Tub
Luxury
Wifi
- Sleeps up to 8
- 4 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
£2,015
Luxury
Car parking on site
Pub within 1 mile
- Sleeps up to 4
- 2 bedrooms
- 3 bathrooms
- Up to 0 pets allowed
3.9
out of 5
7 nights
From
£375
Hot Tub
Luxury
Wifi
- Sleeps up to 6
- 4 bedrooms
- 4 bathrooms
- Up to 2 pets allowed
4.3
out of 5
7 nights
From
£805
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 3 bathrooms
- Up to 1 pet allowed
4.4
out of 5
7 nights
From
£789
Romantic Helmsley Cottages
Hot Tub
Luxury
Wifi
- Sleeps up to 12
- 6 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.8
out of 5
7 nights
From
£1,885
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 8
- 4 bedrooms
- 3 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£679
Wifi
Car parking on site
Pub within 1 mile
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 0 pets allowed
4.7
out of 5
7 nights
From
£689
Luxury
Wifi
Car parking on site
- Sleeps up to 6
- 3 bedrooms
- 2 bathrooms
- Up to 1 pet allowed
4.7
out of 5
7 nights
From
£895
Hot Tub
Luxury
Wifi
- Sleeps up to 8
- 4 bedrooms
- 4 bathrooms
- Up to 3 pets allowed
4.9
out of 5
7 nights
From
£2,015
Luxury
Car parking on site
Pub within 1 mile
- Sleeps up to 4
- 2 bedrooms
- 3 bathrooms
- Up to 0 pets allowed
3.9
out of 5
7 nights
From
£375
Wifi
Car parking on site
Enclosed Garden / Patio
- Sleeps up to 5
- 3 bedrooms
- 2 bathrooms
- Up to 2 pets allowed
5
out of 5
7 nights
From
£685
Hot Tub
Car parking on site
Garden / Patio
- Sleeps up to 2
- 1 bedroom
- 1 bathroom
- Up to 2 pets allowed
5
out of 5
7 nights
From
£445
Wifi
Car parking on site
Garden / Patio
- Sleeps up to 4
- 2 bedrooms
- 1 bathroom
- Up to 1 pet allowed
7 nights
From
£469
Wifi
Car parking on site
Detached
- Sleeps up to 5
- 2 bedrooms
- 1 bathroom
- Up to 0 pets allowed
4.7
out of 5
7 nights
From
£389
Inspiration of things to see and do in our cottages in Helmsley
This picturesque market town in North Yorkshire offers a blend of history, natural beauty, and charming attractions. With the largest collection of Yorkshire cottages, we have the perfect home away from home for you.
Here are the top five things to see and do in our cottages in Helmsley:
Helmsley Castle
Explore Helmsley Castle, a medieval fortress with well-preserved ruins. Climb to the top of the tower for panoramic views of the town and the surrounding countryside.
Rievaulx Abbey
Visit Rievaulx Abbey, a stunning Cistercian monastery located just a short drive from Helmsley. Walk among the atmospheric ruins and appreciate the tranquillity of this historic site.
Duncombe Park
Discover Duncombe Park, a magnificent stately home surrounded by beautiful gardens and parkland. Take a leisurely stroll through the landscaped grounds and enjoy the peaceful atmosphere.
Helmsley Walled Garden
Enjoy the beauty of Helmsley Walled Garden, a five-acre site restored to its former glory. The garden features a wide variety of plants, flowers, and themed areas to explore.
North York Moors National Park
Explore the stunning landscapes of the North York Moors National Park, which surrounds Helmsley. Go for scenic walks, enjoy cycling routes, or simply appreciate the beauty of this expansive national park.
More Popular Holiday Destinations
Explore
Inspiration
Collections
2025 Holiday CottagesAccessible Holiday CottagesChristmas Holiday BreaksCity BreaksCoastal HolidaysCottages with PoolCycling BreaksDog friendlyEV Charging Holiday CottagesFamily HolidaysFebruary Half Term BreaksFishing HolidaysGlamping in the UKGolf BreaksHoliday Cottages with Games RoomHot tub breaksLarge Holiday Cottages & Group AccommodationLast Minute DealsLuxury Holiday CottagesMay Half Term HolidayNew Years Eve BreaksOctober Half Term BreaksQuality CottagesRomantic GetawaysShort Breaks & Weekends AwaySpring Breaks in the UKSummer Holidays in the UKSustaibable & Eco Friendly CottagesUnique CottagesValentines BreaksWaterside BreaksWinter Breaks in the UK
Destinations
Countries
Regions
All West MidlandsBedfordshireBerkshireBlackdown HillsBuckinghamshireCambridgeshireCheshireConstable CountryCornwallCotswoldsCounty DurhamCranborne Chase and West Wiltshire DownsCumbriaDartmoorDerbyshireDevonDorsetEssexExmoorForest of BowlandForest of DeanGloucestershireGreater LondonHampshireHerefordshireHertfordshireHigh WealdHowardian HillsIsle of WightKentKent DownsLake DistrictLancashireLeicestershireLincolnshireLincolnshire WoldsMalvern HillsMendip HillsNew ForestNidderdaleNorfolkNorfolk BroadsNorfolk CoastNorth Devon CoastNorth PenninesNorth Wessex DownsNorthamptonshireNorthumberlandNorthumberland CoastNottinghamshireOxfordshirePeak DistrictRutlandShakespeare CountryShropshireShropshire HillsSomersetSouth DownsStaffordshireSuffolkSuffolk Coast and HeathsSurreySussexWarwickshireWiltshireWorcestershireWye ValleyYorkshireYorkshire DalesYorkshire Moors
Areas
BedaleBeverleyBridlingtonBromptonCaytonClaxtonDanbyDriffieldFileyFlamboroughGlaisdaleGoathlandGrassingtonHarrogateHarwood DaleHawesHaworthHelmsleyHolmfirthIngletonKettlewellKirkbymoorsideLeyburnMalhamMaltonMukerNorthallertonPateley BridgePickeringReethRichmondRiponRobin Hoods BayRosedale AbbeySaltburn-by-the-SeaScarboroughSelbySettleSkiptonStaithesThirskWhitbyYork
Sign up for a chance to win £500!
Stay updated on the latest deals, exclusive offers and new holiday destinations by joining the cottages.com newsletter! Register today and automatically be entered into our prize draw to win a £500 voucher. Click here for terms and conditions.
You can opt out anytime by using the unsubscribe link in our emails. We will use your information as per our Privacy Notice.