Pet-friendly vacation rentals in Helmsley

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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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Guest favorite

Apartment in Gilling East

4.95 out of 5 average rating, 130 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.

Oct 17 – 24

R2,123 ZAR per night

Guest favorite

Home in Helmsley

4.93 out of 5 average rating, 111 reviews

Holiday at 44 - wonderfully situated for all

This spacious accommodation comprising of two lounge areas housing charm-filled woodburners and underfloor heating, a large conservatory used as a dining room, the kitchen has a large american style fridge freezer with a breakfast bar and large rangemaster cooker. Upstairs there are four bedrooms two doubles, one twin and bunk beds, there is also a separate shower room, a separate WC and a fully fitted bathroom. The garden can be accessed via patio doors from the lounge, or the conservatory.

Nov 17 – 24

R5,111 ZAR per night

Guest favorite

Guest suite in Boltby

4.98 out of 5 average rating, 108 reviews

Boltby, Cosy North York Moors Snug with Log Burner

Barn Owl Snug is tucked away in the pretty village of Boltby in the North York Moors National Park. The perfect space to recharge and have a relaxing break. The snug is self-contained. Downstairs is the living, dining and full kitchen area with a log burner for those cosy evenings. Up a spiral staircase is a large, bright bedroom with king size bed and separate full family bathroom. Double doors open onto a private decked area. Washing machine / freezer / bike storage. Wi-Fi and parking.

Nov 14 – 21

R2,042 ZAR per night

Guest favorite

Cottage in East End

4.99 out of 5 average rating, 241 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!

Feb 24 – Mar 3

R3,433 ZAR per night

Guest favorite

Guest suite in Nunnington

4.86 out of 5 average rating, 176 reviews

Renovated 16th century haven in North Yorks Moors

Located 3 miles away from two award winning restaurants with Michelin accolade; The Star Inn & The Pheasant Hotel at Harome. Nunnington is a beautiful village in the North Yorkshire Moors. Overlooking the National trust property and gardens, Nunnington Hall, from your bedroom window. Great location for walking, biking but equally York city center is only 19 miles away. Accommodation is a self contained ground floor suite with direct outdoor access, part of a 16th century almshouse renovation.

Mar 10 – 17

R1,744 ZAR per night

Guest favorite

Guest suite in Rosedale Abbey

4.98 out of 5 average rating, 131 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.

Apr 19 – 26

R2,208 ZAR per night

Guest favorite

Barn in Aislaby, Pickering

4.97 out of 5 average rating, 231 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.

Nov 15 – 22

R4,384 ZAR per night

Guest favorite

Cottage in Sessay

4.95 out of 5 average rating, 222 reviews

The Cobbler's Cottage

Nestled in the scenic North Yorkshire village of Sessay, this charming former cobbler's cottage offers a spacious retreat. Inside, you'll find a wood-burning stove, TV, Blu-ray player, and a modern kitchen equipped with an oven, microwave, dishwasher, fridge freezer, Nespresso coffee maker, and a washing machine. Step outside to a private patio complete with a dining area and barbecue. Plus, we warmly welcome one well-behaved pet, so you can bring your furry friend along if you desire.

Aug 5 – 12

R2,256 ZAR per night

Guest favorite

Guest suite in Skewsby

4.98 out of 5 average rating, 197 reviews

The Lodge, country location in the Howardian Hills

Our Lodge is a complete labour of love. A lovely relaxing space in a rural setting. We are a family of 4 with 2 dogs and chickens amongst other things! Our lovely Lodge is in our garden, up some steps before you enter your own private area with large fenced garden. The Lodge has a kitchen area, log burning stove, 2 comfy armchairs, table and 2 chairs and a double bed. A small door leads to the bathroom, lovely warm towels and underfloor heating. We look forward to welcoming you.

Nov 2 – 9

R2,442 ZAR per night

Guest favorite

Home in Kirkbymoorside

4.9 out of 5 average rating, 299 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.

Dec 9 – 16

R2,202 ZAR per night

Guest favorite

Guest suite in Sutton-on-the-Forest

5.0 out of 5 average rating, 225 reviews

Countryside location near to York

Nestled in the countryside just outside York, 'The Kennel' is a relaxing and peaceful retreat. This small but perfectly formed self-contained annex is set in three acres of newly planted woodland in which you can often see the Barn, Tawny and Little Owls visiting to be fed from the feeding posts, garden, small orchard, wildlife pond and apiary housing up to 8 beehives which provide us with some delicious honey. To the rear of the property is a Whisky and Gin Distillery.

Oct 29 – Nov 5

R1,902 ZAR per night

Guest favorite

Cottage in Helmsley

4.91 out of 5 average rating, 134 reviews

Cliff Stud Retreat, Helmsley, Frankel Cottage

Our 3 bedroom cottage has stunning countryside views due to its location. With a wood burner and cosy decor it's the perfect bolt hole for couple and families alike. Frankel cottage sleeps up to 5 guests (it’s advised 4 adults maximum) and has a fully equipped kitchen inc wm/microwave. The bathroom fully refurbished (shower/bath)is located downstairs. The cottage is close to the centre of Helmsley where you can find many tearooms, pubs & independent shops

Oct 9 – 16

R4,744 ZAR per night