
Vacation rentals in Helmsley
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Top-rated vacation rentals in Helmsley
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Popular amenities for Helmsley vacation rentals
Other great vacation rentals in Helmsley

Luxurious dog friendly barn in Michelin food zone
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

Romantic Cottage with Hot Tub & Countryside Views
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.

Foxglove Cottage
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!

Fox Cottage in lovely Helmsley
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.

Woodland cabin with private lake, sauna + firepit
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

Mill House Annex, Oldstead
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.

Maltkiln House Annexe North Yorkshire moors
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!

charming semi-detached cottage with lovely views
A delightful cottage with all the necessary amenities to make you feel at home!
Quick stats about vacation rentals in Helmsley
Total rentals
40 properties
Nightly prices starting at
G$16,722 GYD 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
Frequently Asked Questions
How much does it cost to stay in house rentals in Helmsley?
Experience the best of Helmsley with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there cottage rentals with a dedicated workspace in Helmsley?
Yes! Work meets play with ease at over 20 cottage rentals in Helmsley featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Helmsley have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly cottage rentals in Helmsley?
Four-legged friends are welcome in Helmsley. Choose from more than 20 cottage rentals for guests traveling with pets.
Do house rentals in Helmsley have free parking?
Absolutely! We offer over 10 house rentals with free parking in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Helmsley have wifi?
Absolutely! We offer over 20 cottage rentals with wifi in Helmsley. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Helmsley?
Helmsley has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Helmsley?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
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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