
Cottage vacation rentals in Helmsley
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Helmsley
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Helmsley cottage rentals
Cottage rentals with a hot tub

Holly Cottage, hidden gem in the Yorkshire wolds

Highbury Farm Cottage with Hot Tub. Pet friendly

Jenson Cottage - Env Friendly & Private Hot Tub

3 Railway Cottage Pickering , Hot Tub, Pets all'd

Salt water hot tub, dog friendly & village pub

1700 Period cottage in the Heart of Old Addingham

Orchard House, luxury cottage retreat.

The Little Secret 8 sleeps 2-4 with Hot tub
Pet-friendly cottage rentals

Charming two bedroom cottage

Superb conversion with spectacular views

Preston Mill Loft, with outstanding views.

Romance or a rest at The Nest Castleton,Whitby!

Cosy two-bed cottage. Sleeps 4. Pets welcome.

Amber Cottage ( with parking)

Cottage on the Green next to historic castle

Forge Cottage - cosy beach cottage
Private cottage rentals

Curlew Cottage, Near Ripon, Yorkshire sleeps 4

Willow Cottage nestled twixt coast and moorland

charming 2 bed cottage located on small farm

Idyllic and stylish private cottage by the stream

Autumn Cottage

Cargate Cottage

Sun Cottage, a romantic couples retreat.

Secluded rural 2 bedroom cottage near York
Quick stats about cottage rentals in Helmsley
Total rentals
20 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
700 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Yorkshire Dales national park
- Flamingo Land Resort
- Harewood House
- Durham Cathedral
- North Yorkshire Water Park
- Fountains Abbey
- Royal Armouries Museum
- York Castle Museum
- Scarborough Beach
- The Bowes Museum
- Saltburn Beach
- Locomotion
- Cayton Bay
- Scarborough South Cliff Golf Club
- Filey Beach
- National Railway Museum
- Hartlepool Sea Front
- Malham Cove
- Studley Royal Park
- Ryedale Vineyards
- York Art Gallery
- Ganton Golf Club
- Whitby Beach
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
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- Kid-friendly state parks Check out these family-friendly hikes