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Popular Cottages
- Rosedale - Port Mulgrave
- Bear Lodge
- Meadowbank Lodge
- Bramble Retreat
- Stags Mount
- Lonsdale Villa
- Wayside Cottage
- Seascape Villa
- Foxes Den
- Lake View Lodge
- Old Station Farm
- Meadowsweet
- The Old Doghouse
- Thompson Rigg House
- Roe Deer Cottage
- Roe Deer Lodge
- Mels House
- Senna Rocks
- 315 Filey Road
- Wellington Lodge
- Silverwood Lodge
- Low Shipley Cottage
- High Croft
- Rising Sun
- Willow Breeze At Breeze Farm
- Peak View At Boots And Bubbles
- 23 Trafalgar Square
- Broad Bay Lodge
- Owen Well Barn
- Nuthatch Lodge Woodlands Collection
Helmsley Holiday Cottages
Rated Top 5 Most Popular Places in Vale of York 2026 by our visitors
Our curated collection of Helmsley cottages has something for everyone... Whether you're idea of a great holiday is a modern glamping pod, or a rustic thatched cottage that's a hundred years old, we've got you covered! Each of our rentals features a private hot tub and everything you need for your next family holiday, romantic retreat or that getaway with a group of friends. Discover find your perfect Helmsley holiday home today.
- Private hot tub in courtyard
- Working wood burner in lounge
- Two dogs welcome
- Steps from Helmsley town centre
- Cleveland Way from the door
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Visitor Rating
4.8
- Private hot tub in enclosed garden
- Three en-suite bedrooms sleep six
- Two dogs welcome with private field
- Tennis court and billiards room access
- Wood burner in 30-foot living area
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Visitor Rating
4.8
- Private hot tub with sea views
- Games room with pool table
- Homemade welcome treats
- Dog-friendly coastal location
- Luxury touches throughout
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Visitor Rating
5
- Private hot tub
- Spotlessly clean cabin
- Helpful attentive hosts
- Perfect peaceful location
- Cosy woodburning stove
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Visitor Rating
5
- Wood-fired hot tub
- Spotlessly clean modern interiors
- Walks from the doorstep
- Attentive helpful hosts
- Perfect romantic retreat
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Visitor Rating
4.8
- Private hot tub with countryside views
- Peaceful rural location
- Close to York and Castle Howard
- Thoughtful welcome hamper
- Comfortable and well-equipped accommodation
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Visitor Rating
4.8
- Four-poster beds
- Hot tub in private courtyard
- Huge dining table for gatherings
- Near Castle Howard and York
- Beautiful Georgian property with gardens
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- Luxury marble finishes
- Private hot tub
- Horse stables available
- Two woodburning stoves
- Near York and National Parks
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Visitor Rating
5
- Stunning countryside views
- Hot tub with pagoda
- Huge kitchen with two dishwashers
- Ground floor disabled access
- High-quality luxury furnishings
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Visitor Rating
5
- Private hot tub on sheltered patio
- Pub just 50 yards away
- Pizza oven and outdoor kitchen
- Wood burner in open-plan lounge
- Two dogs welcome
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Visitor Rating
5
- 15 minutes from historic York
- Private hot tub with countryside views
- Four-poster bed and luxury bathrooms
- Dog-friendly with enclosed garden
- High-quality finish throughout
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- Luxury hot tub with rural views
- Dual-aspect wood burner, two lounges
- Working farm, open countryside setting
- 2.5 miles from Flamingo Land
- Sleeps 6, dogs welcome
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- Private hot tub with countryside views
- Two en-suite bedrooms for privacy
- Bi-folding doors to enclosed patio
- Working farm with doorstep walks
- Near Flamingo Land and coast
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- Private hot tub on decking
- Three bedrooms sleeping six guests
- PlayStation 4 and Smart TVs
- Welcomes up to three dogs
- Near Flamingo Land theme park
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- Private hot tub on deck
- 20-acre enclosed dog field on site
- 2 miles from steam railway
- Sleeps 4 with king and twin
- PlayStation 4 and Smart TV
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- Private hot tub in enclosed garden
- Secure 20-acre off-lead dog field
- Stone cottage with rural views
- 2 miles from Moors Railway
- Wood-burner and hotel-style linen
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- Private hot tub with countryside views
- 20-acre enclosed dog walking field
- Sleeps 6 in 3 bedrooms
- PS4 and Smart TVs throughout
- 2 miles from Moors Railway
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- Private hot tub under canopy
- Secure 20-acre dog field
- Hypnos mattresses in both bedrooms
- PlayStation 4 in twin room
- 2 miles from steam railway
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- Private hot tub on enclosed patio
- Dogs welcome up to 3
- 1 mile from Pickering and Thornton-le-Dale
- Wood burner in open-plan lounge
- 5.5 miles from Flamingo Land
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- Private hot tub included
- Enclosed garden dogs welcome
- North York Moors National Park location
- Two en-suite bedrooms sleeping four
- 1 mile from Pickering
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- Private covered hot tub
- Up to 3 dogs welcome
- Scandinavian timber lodge
- 1 mile from Pickering
- North York Moors location
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- Private hot tub on decked terrace
- 20-acre on-site dog walking field
- Sleeps 6 across 3 bedrooms
- 1 mile from Pickering town
- Smart TVs in every bedroom
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- Private hot tub on the decking
- Next to private woodland
- Sleeps 4 family layout
- 3 dogs welcome
- 1 mile from Pickering
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- Private hot tub with canopy
- Up to 3 dogs welcome
- Hypnos beds in both rooms
- 5 miles from Flamingo Land
- 60-acre woodland site
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- Private hot tub on enclosed deck
- Up to three dogs welcome
- North Yorkshire Moors on the doorstep
- King-size en-suite bedroom
- Flamingo Land 5.5 miles away
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- Private covered hot tub included
- Up to 3 dogs welcome
- 60-acre woodland estate
- Under 1 mile from Pickering
- Scandi lodge sleeps 4
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- Sleeps 15 across six bedrooms
- Shared pool, hot tub and sauna
- North Yorkshire Moors National Park location
- Private parking for five cars
- Welcomes up to three dogs
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Visitor Rating
4.7
- Private secluded garden
- Hot tub under the stars
- Minutes from Malton town centre
- Comfortable king-size bed
- Easy access to York
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- Eight-seater private hot tub
- Working farm with countryside views
- Wood-burner and dual lounges
- 2.5 miles from Flamingo Land
- Sleeps 2 plus children's snug
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Visitor Rating
5
- Private hot tub
- Games room with pool table
- Accessible ground-floor bedroom
- Working farm location
- Perfect for family gatherings
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