
Holiday rentals in Helmsley
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Top-rated holiday rentals in Helmsley
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Helmsley
Top guest favourite

Barn in Stearsby
5 out of 5 average rating, 44 reviewsLuxurious dog friendly barn in Michelin food zone
NicolaRating, 5 stars1 day ago
Absolutely beautiful converted barn in a peaceful location with stunning views & walks on the doorstep. Barn was spotless, comfortable and tastefully decorated with everything you could need. Really appreciated the personal touches. We were welcomed with freshly baked bread and homemade cake. Lots of recommendations for places to visit and eat. We loved Castle Howard and the stunning countryside. Highly recommended and we can’t wait to come back
Top guest favourite

Cottage in Helmsley
5 out of 5 average rating, 25 reviewsRomantic Cottage with Hot Tub & Countryside Views
PaulRating, 5 stars1 week ago
One of the best Airbnb cottages we have stayed in…recently decorated, tasteful furnishings, lovely gardens and everything we needed for our stay. It is a 30min walk into town, but is a flat walk along the old railway track so an easy stroll. We went to Beadlam Grange Cafe for breakfast which is a 5-10min stroll from the cottage too.
Guest favourite

Cottage in Laskill
4.82 out of 5 average rating, 79 reviewsFoxglove Cottage
JordanRating, 5 stars1 week ago
We had a wonderful short stay at the Foxglove Cottage in Laskill to celebrate our first wedding anniversary. The cottage was cosy, clean, and perfectly placed. Peaceful countryside views and a truly relaxing atmosphere. Our dog loved it too, very pet-friendly with great space to explore. A perfect little getaway, and we’d love to return!
Superhost

Cottage in Helmsley
4.8 out of 5 average rating, 20 reviewsFox Cottage in lovely Helmsley
NatalieRating, 5 stars5 months ago
The Cottage is idyllic and in an excellent location in the heart of Helmsley. It felt private and the cottage was very cosy with lots of amenities, it really is the little things, plenty of tea towels, bathroom towels, dishwasher tablets etc. It was a real treat to have such a large bathroom and a surprise in a cottage. It was just a nice short walk to all the lovely shops, pubs, cafes and restaurants. Ben was very responsive and had left lots of recommendations. I would definitely recommend staying here.
Top guest favourite

Cabin in Kennythorpe
5 out of 5 average rating, 56 reviewsWoodland cabin with private lake, sauna + firepit
TheresaRating, 5 stars2 weeks ago
We have just got home, after a lovely 2 night stay at the Kingfisher cabin. The cabin is beautiful and in the most relaxing setting - set in the middle of the woods, over looking a small lake. Very peaceful and surrounded by wildlife ❤️ The cabin was modern, clean and everything was to a high standard. The sauna and hot bath (lovely and warm) were fantastic and like a mini spa in the middle of the forest. We would love to come back for another stay x x
Top guest favourite

Guest house in Oldstead
5 out of 5 average rating, 80 reviewsMill House Annex, Oldstead
JuliaRating, 5 stars1 week ago
We had a lovely two-night stay at this well appointed Airbnb. The space is light, spacious, and very restful – ideal for a peaceful break. Set in a lovely, location, it had a gorgeous view of the garden and a charming little patio area to enjoy it from. It’s slightly off the beaten track but there’s plenty of interesting walks and places to visit in the surrounding area. The hosts were extremely welcoming. There were thoughtful touches throughout, including welcome items of bread, milk, eggs, and fresh flowers that made the place feel inviting. I would highly recommend this place to anyone looking for a quiet and comfortable getaway in a beautiful setting.
Top guest favourite

Tiny home in Urra
4.97 out of 5 average rating, 79 reviewsMaltkiln House Annexe North Yorkshire moors
SimonRating, 5 stars5 days ago
We had an amazing couple of nights here for a joint wedding anniversary and birthday. The place itself is fantastic and very nicely decorated. The setting itself is perfect for a countryside getaway. It was spotless and Laura and her husband were so accommodating and helped us with anything we needed including picking us up when we got slightly lost walking back! We will be coming back again at some point as the walks nearby are incredible. Thank you for having us and we would recommend to anyone especially people who have a dog, ours loved it there!
Top guest favourite

Cottage in Oswaldkirk
4.98 out of 5 average rating, 44 reviewscharming semi-detached cottage with lovely views
CharlesRating, 5 stars3 weeks ago
A delightful cottage with all the necessary amenities to make you feel at home!
Quick stats about holiday rentals in Helmsley
Total rentals
40 properties
Nightly prices starting at
₹6,942 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Yorkshire Holiday rentals
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- Yorkshire Dales national park
- The Bay Filey
- Flamingo Land Resort
- yorkshire dales
- Durham Cathedral
- Harewood House
- Fountains Abbey
- Filey Beach
- North Yorkshire Water Park
- National Railway Museum
- Royal Armouries Museum
- Cayton Bay
- Scarborough Beach
- York Castle Museum
- Scarborough South Cliff Golf Club
- Hartlepool Sea Front
- Malham Cove
- Saltburn Beach
- Studley Royal Park
- Locomotion
- Ganton Golf Club
- The Bowes Museum
- Ryedale Vineyards
- York Art Gallery