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Pet-friendly vacation rentals in Helmsley

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Helmsley

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Cottage in Staithes

4.81 out of 5 average rating, 160 reviews

17th Century fisherman's cottage + stunning view

Wake up to this stunning view, relax, and enjoy your morning coffee, afternoon tea or early evening G&T sitting outside our traditional cottage gazing at the fishing boats in the beck, higgledy-piggledy rooftops or out to sea. Regularly stayed in and painted by artists, this charming 17th Century cruck-beamed fisherman's cottage is quaint and cosy + open fire-ideal for a romantic getaway or walking holiday. Mortimer & Whitehouse stayed and filmed their Gone Fishing Christmas Special here 2020.

Rental unit in Gilling East

4.96 out of 5 average rating, 156 reviews

Fairfax View - delightful annexe cottage, Gilling

Situated in the picturesque village of Gilling East on the edge of the North York Moors national park, Fairfax View offers the perfect base to explore this beautiful corner of Yorkshire. This one bedroom cottage has en-suite shower room, well equipped kitchen and large lounge with double sofa bed (available for use by prior request). Located directly opposite the highly-acclaimed Fairfax Arms and on the edge of the Ampleforth Abbey and College campus, with a 9 hole golf course in the village.

Tiny home in North Yorkshire

4.92 out of 5 average rating, 315 reviews

Diamond Den- a quiet, peaceful and private haven.

Situated in the extremely peaceful village of Butterwick, just a few moments walk to the river rye and bridge, Diamond Den is the perfect retreat. Being at the foot of the Howardian Hills provides a wealth of walking opportunities and we are just a short drive away from some spectacular market towns, including Helmsley (8m) Malton( 5.4m), Ampleforth (9.7m) and Pickering (8.5m). You will have your own private garden space and parking. ACCESS TO THE SLEEPING AREA IS UP A LADDER- PLEASE SEE IMAGES

Cottage in East End

4.99 out of 5 average rating, 269 reviews

The Owlets, Ampleforth

A luxury self-catering holiday cottage nestled on the edge of the North York Moors National Park in the pretty village of Ampleforth. The Owlets is a 19th century single storey stone outhouse that has been recently renovated to a high standard with brand new fixtures and fittings, as well as traditional features such as solid oak floors and beams. We are located just 1 mile from Ampleforth College, and 4 miles from Helmsley. All welcome, including children of all ages and well behaved pets!

Cottage in North Yorkshire

4.99 out of 5 average rating, 110 reviews

Charlie’s barn. A stunning barn conversion

Unwind in our stunning 18th century, 1 bed barn conversion with beamed ceilings and open plan living space. Outside there is a south facing secure court yard with your own private access. Situated in a tranquil village within an area of outstanding natural beauty. The village boasts a fine dining pub with other local pubs within a short distance or even visit Malton the food capital. A perfect base for biking , walking or visiting Castle Howard, the North Yorkshire moors , East coast or York.

Cottage in North Yorkshire

4.91 out of 5 average rating, 242 reviews

Cosy character cottage in heart of Pickering

31 Eastgate is a cosy and well equipped cottage in a fantastic central location in the market town of Pickering. It's ideally located for exploring the North Yorkshire Moors, Scarborough, Whitby and the historic walled city of York. Located on one of the main roads in Pickering (sometimes there will be traffic noise) the tree lined street of Eastgate is beautiful in all seasons and the town centre is a 5 minute walk away. Visit one of the fantastic pubs or catch a steam train to Whitby.

Guest suite in Rosedale Abbey

4.99 out of 5 average rating, 169 reviews

Cosy rural cottage in National Park

Come and stay in the beautiful village of Rosedale Abbey in the spectacular North Yorkshire Moors National Park. Moo’s is our converted stone cottage with a lovely living kitchen with cast iron stove and a vintage country feel. A handmade turned staircase leads up to the en-suite bedroom with metal bed stead and roll top bath. Adjacent there is a spacious covered patio area with seating, dining and storage, which looks across to an outdoor patio with fruit trees seating and parking space.

Barn in Aislaby, Pickering

4.96 out of 5 average rating, 263 reviews

Stunning views, 4 acres, dog friendly, Yorkshire

Owl House is an Elizabethan barn conversion designed by architects Bramhall Blenkharn Leonard. It sits on the edge of North York Moors National Park and features a glazed wall offering far reaching countryside views across the vale of pickering with the Howardian Hills visible in the distance. Former farm set in 4 acres of peaceful gardens, paddock, woodland & chickens. Dog friendly. Open plan sitting room/kitchen, bathroom w shower,mezzanine bedroom,pizza oven,parking, walkable pub.

Home in Kirkbymoorside

4.9 out of 5 average rating, 354 reviews

Oakforge Cottage, a spacious home from home.

Oakforge Cottage is a 3 storey house in the Market Town of Kirkbymoorside. It offers comfortable accommodation for up to 5 people (and up to 2 well behaved dogs).PLEASE NOTE: WE HAVE NO OUTSIDE SPACE FOR THE EXERCISING OF DOGS. With a fully equipped kitchen, living room with realistic simulated log burner and two bathrooms, guests will instantly feel at home in our warm, well furnished, self-catering holiday cottage. Check-in time is after 3PM, Check out is now 10.00AM.

Barn in North Yorkshire

4.92 out of 5 average rating, 200 reviews

Delightful Barn with log burner near Pickering

A tranquil, 19th century converted barn with private garden and outdoor fire overlooking the local countryside. A short drive from Pickering and close to the Moors, Whitby and York, the barn is great for a relaxing break. Inside, you will find a renovated living area, with a wood burning stove, Smart TV and fully fitted kitchen complete with oven, fridge washing machine and dish washer, the barn offers everything you will need for a relaxing getaway in Yorkshire.

Home in Hovingham

4.89 out of 5 average rating, 133 reviews

The Shed, Hovingham, York

An exquisite quaint barn conversion tucked away in the breathtaking Howardian Hills Area of Outstanding Natural Beauty. Take a look at this exquisite bijou barn conversion tucked away in the Howardian Hills - an Area of Outstanding Natural Beauty. Located 17 miles north of York, this romantic cottage ticks every box in terms of interiors, location and charm. It's the perfect choice for couples looking to escape to the country in style. Dogs are welcome.

Home in Helmsley

4.94 out of 5 average rating, 242 reviews

Clothes Prop Cottage, a Helmsley hideaway

Clothes Prop Cottage is located in the heart of Helmsley, just a couple of minutes walk from the shops, tea rooms, pubs and restaurants in this beautiful North Yorkshire market town. The property is available for 3 night weekend and 4 night mid week stays as well as full 7 night breaks. The property suits couples looking for a relaxing stay in the Yorkshire countryside, with their beloved pets welcome!

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Popular amenities for Helmsley pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Masham

4.99 out of 5 average rating, 169 reviews

Cosy & charming 2 bedroom home with roof terrace

Home in Malton

4.95 out of 5 average rating, 124 reviews

Luxury one bedroom cottage with log burning hot tu

Home in Burton Leonard

4.99 out of 5 average rating, 128 reviews

Luxury 3 bedroom house - hot tub & amazing view!

Home in North Yorkshire

4.93 out of 5 average rating, 294 reviews

Narnia

Home in High Hawsker

4.91 out of 5 average rating, 237 reviews

Hawthorn Cottage - delightful and welcoming

Home in Hinderwell

4.95 out of 5 average rating, 116 reviews

Crabapple Cottage close to Runswick Bay & Staithes

Home in Westerdale

4.96 out of 5 average rating, 139 reviews

Beautiful, quiet and private historic Coach House

Home in Guisborough

4.91 out of 5 average rating, 187 reviews

Stoney Nook Cottage

Pet-friendly home rentals with a pool

Home in The Bay

4.94 out of 5 average rating, 141 reviews

Sandy Toes, The Bay, Filey

Rental unit in Langton

4.79 out of 5 average rating, 179 reviews

Jubilee Apartment 1

Home in North Yorkshire

4.9 out of 5 average rating, 73 reviews

three bedroomed house with stunning sea views

Rental unit in North Yorkshire

4.86 out of 5 average rating, 152 reviews

Filey Bay Cove The Bay Filey Wifi Pets Pool Gym

Condo in North Yorkshire

4.92 out of 5 average rating, 170 reviews

Yorkshire Coast Retreat The Bay Filey Wifi Pets

Home in North Yorkshire

4.95 out of 5 average rating, 125 reviews

Lobster Pot -Award Winning Complex- The Bay, Filey

Home in Cayton Bay

4.9 out of 5 average rating, 117 reviews

Brand new 2021 ABI WINDERMERE STATIC Cedar 1

Cabin in Filey

4.99 out of 5 average rating, 136 reviews

Secret Of Eden Lake View Lodge - Pets/Beach/E.V

Private, pet-friendly home rentals

Loft in Whitby

4.88 out of 5 average rating, 560 reviews

Incredible views, Central Location, Whitby

Barn in Scagglethorpe

4.98 out of 5 average rating, 108 reviews

Cosy Stable in Scagglethorpe

Cottage in Commondale

4.93 out of 5 average rating, 104 reviews

Winnow Cottage . in the Heart of the NY Moors

Cottage in Danby

5 out of 5 average rating, 466 reviews

Farm Cottage with Stunning Views.

Cottage in North Yorkshire

4.93 out of 5 average rating, 534 reviews

Entire Home Cozy little cottage with log burner

Guest suite in Sutton-on-the-Forest

5 out of 5 average rating, 241 reviews

Countryside location near to York

Cottage in North Yorkshire

4.94 out of 5 average rating, 354 reviews

Castlegate Cottage

Cottage in East Riding of Yorkshire

4.97 out of 5 average rating, 362 reviews

The Hayloft at Bainton - 2 bedroom cottage.

Quick stats about vacation rentals that are pet-friendly in Helmsley

Total rentals
20 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
860 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore