Cottage vacation rentals in Helmsley

We had a fantastic stay at Tim’s place! The location was perfect – just around the corner from local amenities and right in the heart of town. It was also only about 10 minutes to the forest and around 30 minutes to Whitby, which made day trips really easy. The hot tub was spotless and ready to use as soon as we arrived, and we were greeted with a lovely bottle of Prosecco – such a thoughtful touch. Tim was an incredibly responsive and understanding host throughout our stay. We’ll definitely be back in the future

Had a lovely weekend at this cottage for my partner’s birthday. Hot tub was gorgeous, even better in the rain. House was beautiful and having the chickens running around outside was fabulous. Marisa was the perfect host. Answered questions quickly and was very accommodating. Would definitely recommend a stay in this lovely cottage.

3 Railway Cottage is a fantastic base to explore the amazing beauty of North Yorkshire. The cottage is located a 20 minute walk from the centre of Pickering but is in a really quiet and private location. The only exception of course is the opportunity to wave at the heritage railway trains that pass at the back of the cottage a few times a day which is really amazing, especially if you wave from the comfort of the hot tub! I can’t recommend this location highly enough, it is a really comfortable and well equipped cottage in a fantastic location - what more could you ask for?

We had a fantastic stay here for 4 nights. It was beautifully clean and had everything and more we needed. Such lovely hosts, very responsive should you need them. Great location! Such an easy drive to a lot of places. We visited Whitby, Scarborough, Pickering, Thornton Le Dale and more! All under 1 hours drive away. Cottage is so homely and very welcoming 😊 Amazing that each room has their own en-suite. Beds are so comfy! Downstairs bedroom was great for us with someone in the party having mobility issues. Games room is a fabulous touch! Sauna and hot tub both very clean. Highly recommend to stay here. Thanks for a wonderful stay 🥰

what an absolutely amazing place to visit, with one of the moat picturesque views of the Yorkshire Dale anyone could wish from right in the backgarden. the cottage is spotless and has everything you could want for a break away.

Lovely cottage in a great location. Walking the surrounding area from the house was great and very near to a pub and tearoom which both served great food. The hot tub was an added bonus!

Really enjoyable stay. Everything was perfect, and I would return if I were back in the area. The location was peaceful, private, and surrounded by beautiful nature — exactly what I was hoping for. The space was spotless, cozy, and thoughtfully designed, with all the amenities I needed for a comfortable and relaxing getaway.

We have just returned from a few nights away staying at this little piece of paradise. If you’re after a tranquil, relaxing holiday then this is the place to stay. From the house itself, to the spectacular views , the amazing pool house and the lovely, friendly neighbours, this place ticks all the boxes and more. Highly recommend visiting The Queens Arms for a meal (or just a cheeky drink), the staff are so friendly and just made our time away extra special. Malham is only a 20 min (ish) drive away and is stunning (a must see). The only thing I would advise is to make sure you take plenty of supplies (or do an online shop for delivery as we did) as the local shop is a 20min drive away. Thankyou again David, we will definitely be back.

We had such a beautiful stay, Sarah's property was just what we needed. We will be back again for certain. The property smelt beautiful the moment you entered the door, it is finished beautifully. The beds are comfortable. The views are magnificent. Local pubs, restaurants and amenities are welcoming and delicious.

A beautiful cottage in a fantastic setting. The complementary eggs,bread and milk were much appreciated and the kitchen was stocked with everything you might need. Will definately be back

Had a fabulous stay in lovely place. Brilliant location for travelling to other places. The house is situated a few mins walking distance out of the town centre, castle and Museum. We had a few stop offs at the Sun Inn on our way back and enjoyed the atmosphere. The house is well equipped and clean. We loved the main living room with its open beams and ceiling. Gill was always available and very helpful 😊

The cottage was perfect for our weekend doing a bike event. It was clean and tidy. We liked the fact we could get the cars off the road.

Such comfy beds. A bed upstairs and a sofa bed downstairs both great. Excellent.

Just had the cosiest stay at Triangle Cottage! Very tastefully decorated, the comfiest bed and the dreamy rolled top bath with the views made it all the more relaxing! It had everything I needed for a wee retreat with my dog in the countryside. Perfect walkable distance to the city centre and various hikes around. Strongly recommend!

We are a family of 3 generations and the property suited us perfectly. Excellent location for Ampleforth College and beyond. Helmsley Pickering and further afield. Very easy to communicate with Marian who gets straight back to you when contacted. An excellent property and lovely and warm in winter. Good parking space directly outside the property.

Warm and comfortable cottage. It was obvious the Jenny had given a lot of thought into how the cottage was set up. The kitchen had all the basics needed for preparing meals. Tea, coffee and some nice biscuit and a welcome bottle of wine. The lounge was cosy and there were files of useful information about the house and the local area. The bed was comfortable. The bathroom had lots of essentials, the shower was great and lots of hot water….there was also a bath. We had taken our bikes and it was great to have a summer house to store them in. The area was really quiet. We really enjoyed our weeks stay.

What a lovely place this is. Thank you so much David 😊 would definitely recommend this place, it's so cute. We'd also recommended local places Riverhead brewery, peel st social, zapato brewery, handmade bakery. Walks on the doorstep, canal on the doorstep too. Absolutely beautiful surroundings. Rogers bakery too but it's only open Saturdays and we missed it.

As always, we had a wonderful stay at the Granary. Duncan and Adrian are the best hosts, and there is nowhere more idyllic and beautiful than lovely Levisham. Thanks again for having us- we will be back!

We had a lovely stay at the cottage: everything was clean, comfortable and good quality. It’s in a super peaceful location, just birdsong and the occasional baa of the sheep neighbours! It’s also in a great location for exploring the area, just 30 mins from the coast and there are lots of beautiful villages on the moor. Highly recommended by us!

We have just spent the most wonderful week at Crossing Cottage. It is charming, peaceful, idyllic and surrounded by nature but also close enough to any amenities, shops and restaurants in the pretty town of Helmsley. On arrival the cottage was immaculate with comfy beds, great shower and toiletries, kitchen with everything you might need and the wood fired hot tub which we spent many evenings enjoying. Thank you Karen for your hospitality, the bottle of fizz and goodies on arrival and your attention to detail. Crossing cottage is truly a very special place to stay.

We had a lovely stay, great location and excellent view, very clean and had everything we could have asked for. Penny gave very clear information about where to park and local restaurants.

When we arrived we were greated by Carolyn and Brian, Brian was just about to take Ruby (the dog) for a walk so Carolyn showed us around the apartment, it's a beautiful place to stay and would highly recommend it. The bed was very comfy and the bathroom/shower room is immaculate! The scenery is stunning and we managed to see the deer and a barn owl too!! We just wish we could have stayed longer!! We would just like to say a 'Big Thank You' to you both for making our stay such a lovely and welcoming one! We hope to see you again soon! Sue and Pete 😊 xxx

Fernbeck Cottage is everything you would want in a Yorkshire get away. It is so lovely , like many others we return time and time again. This beautiful cottage deserves six stars . Everything about it is very special from its perfect location to the high standards throughout the cottage. Vicky and Matthew are the most wonderful hosts. We came away from our visit thinking, when could we visit again . Fernbeck Cottage should be used as a benchmark for all Airbnb hosts.

I can’t speak highly enough of Hayloft - a fantastic peaceful property in a beautiful location. Cosy, tastefully decorated and well equipped - first class from top to bottom. Great walks from the door and lots to see and do if venturing out in the car. Fiona was the perfect host and we only wish we could have stayed longer. We will return!