Cottage holiday rentals in Helmsley

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 🥰

Our second time at the gorgeous Preston Mill Loft and it was just as wonderful as we remember. Super dog friendly, the upgraded hot tub is IMMENSE, comfy bed, welcoming hosts, beautiful scenery, well stocked kitchen. The lot. Cannot recommend highly enough!

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!

Our stay was fantastic, the cottage is so very spacious and well equipped we had everything we needed for an amazing stay.

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 perfect spot for a calm, away from it stay for us. Felt at home straight away, slept brilliantly and so handy for delightful walks to and from the village pubs. Monty our dog felt the same! Owner and local lady housekeeper could not have been more helpful. Impossible to fault - many thanks Andrew

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.

We had a fantastic stay at this peaceful little cottage. Jon kept in touch to make sure everything was going well and we very much appreciated the offer of a fan for the hot weather!

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.

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 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.

We had a great week in the Cow Byre.Beautiful cottage with wonderful views. Everything to a very high standard. Nigel & Clare wonderful hosts. Lots of great places nearby to visit. Highly recommended and will definitely return. Thanks Charlie & Teresa.

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!

Thank you Margaret for a stay we will always remember with great fondness. The cottage is picture perfect, beautifully decorated, and character filled with everything you could possibly need. The location is perfect, with Whitby and Robins Hood Bay close by. We were not expecting how spectacular the country side is, and the views from the cottage were stunning. Margaret is the perfect host, and her accomodation is of the highest quality. Ten out if Ten from us!