
Cottage holiday rentals in Helmsley
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Top-rated cottage rentals in Helmsley
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Popular amenities for cottage rentals in Helmsley
Cottage rentals with a hot tub

Highbury Farm Cottage with Hot Tub. Pet friendly
Really beautiful stay. lovely cottage. can't wait to bring my children back with us next time. Marisa was such a lovely host too!

Jenson Cottage - Env Friendly & Private Hot Tub
We had a wonderful 3 days with our two children. The cottage was very comfortable and everything was an experience. Beautiful artwork, amazing bathroom and our own outdoor space. We would highly recommend and we look forward to going back!

3 Railway Cottage Pickering , Hot Tub, Pets all'd
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?

Salt water hot tub, dog friendly & village pub
Just back from the most relaxing weekend we’ve had for a long time. Gemma’s cottage is beautiful. It’s clean, modern and has everything you could ask for. We visited the pub opposite for meals and everyone was so friendly. We just loved our time there! Gemma is a great host, she is responsive and so kind. When we’ve stopped in other places the rules what you can and can’t do are sometimes quite off putting (I understand it’s your home and you want everyone to respect it though) Gemma is so laid back and this I think makes you respect the space and house more (well id like to think most people are the same as us) so we felt very relaxed. The hot tub is great and amenities. We are definitely coming back for another relaxing weekend. Thank you Gemma xx

Spa Garden Cottage - Upper Hopton
What a great find this property was! From the initial booking until the time we left Scarlett was responsive to all queries. The property was exactly as described and a lovely place to relax. The hot tub was an added bonus which we enjoyed in the evening sun. Wish we could have stayed longer!

1700 Period cottage in the Heart of Old Addingham
Just returned from a 2 night stay at this lovely cozy cottage in the beautiful village of Addingham. The cottage was nice and clean with welcoming goodies on arrival. Lorraine provided is us with useful information of places to visit around the location and how to access the parking space before we arrived. The hot tub is so relaxing after a nice walk. We will definitely be back again. Thank you Lorraine & Hayley.

Orchard House, luxury cottage retreat.
Wow! What a find! The house is stunningly situated amongst amazing views and surrounded by nature and wildlife. We loved looking out across the hills from the hot tub and playing in the field in front of the house and on the swings down by the pond. The village is in close walking distance even with a 3 year old in tow. The cottage itself feels special with beautiful wooden furniture which I assume comes from the timber farm it’s on. The rooms are spacious yet have that cosy cottage feel. The hosts are friendly, responsive and helpful without being intrusive - they were on hand as and when we needed them. Overall, a wonderful 2 night break was enjoyed and we would love to stay here again!

L'aal Cottage Reighton Filey Coast Hot tub
We had a lovely time at L’aal Cottage. Great use of the space, everything of high standard and fully equipped for an enjoyable stay. Jan was friendly and made us very welcome. Great spot for exploring the Yorkshire coast and a great walk along the beach to Filey.
Pet-friendly cottage rentals

Superb conversion with spectacular views
Had a wonderful time at this lovely location. Beautiful place and great hosts. Would definitely stay again.

Preston Mill Loft, with outstanding views.
Really great hosts, very helpful and friendly, a joy to deal with.

Romance or a rest at The Nest Castleton,Whitby!
Lovely little cottage in great location. Easy access to North Yorkshire dales and coast. Cottage had all amenities and was spotless. Will definitely stay again.

Cosy two-bed cottage. Sleeps 4. Pets welcome.
Wonderful cottage. Very well equipped kitchen. Beds were very comfortable especially the double room. Everywhere was spotlessly clean and tidy. Extra touches such as tea and biscuits was a nice surprise. The location is right in the heart of Staithes with everything you would need within a 5 minute walk. We parked easily at bank top car park and walked to the cottage. Only suggestion would be the smaller sofa (non leather) isn’t very comfortable.

Amber Cottage ( with parking)
This cottage is lovely and we felt right at home. The location is perfect for exploring Whitby. Everything is a short walk away and despite being near a main road the cottage was very quiet. Would definitely recommend!

Cottage on the Green next to historic castle
Simply wonderful : we can not think of a single thing that was not 100%, everything exceeded our expectations. Definitely not a soulless corporate run Airbnb! The interior design was outstanding and individual without being overpowering, adding to the sense of calm that the location gives. Super clean throughout. Oh and the bedding, it was out of this world. Everything we needed was provided, the log burner a joy in the chillier evenings. Great walks and the bus stop is directly opposite (every 3 hours, check the timetable, the drivers don’t linger) into York.

Forge Cottage - cosy beach cottage
We had such a lovely time staying in this beautiful Airbnb in Robin Hood’s Bay. The location was perfect - picturesque, and just a short walk to everything we needed. Mark and Aaron’s home is spotlessly clean, well-equipped, and full of thoughtful touches that made it feel like a real home from home. Communication was excellent throughout, and we felt truly looked after. We wouldn’t hesitate to return, actually we will return - thank you for a wonderful stay!

Peaceful riverside cottage.
Fantastic few days away, gargrave is lovely. Good walks from the door, close to Malham. Great pub food, fish and chips shop and co-op nice cafe. Very friendly. Hose immaculate with riverside view.
Private cottage rentals

Curlew Cottage, Near Ripon, Yorkshire sleeps 4
We had a really lovely stay at Curlew Cottage for my husbands 40th birthday weekend. It was a great base to explore the surrounding area as we are into our walks. The house itself was beautifully presented, spacious, very clean and had everything we needed. The setting was very peaceful with beautiful views all around. We spotted lots of wildlife which was lovely. We would highly recommend and hope to visit again in the future.

Willow Cottage nestled twixt coast and moorland
We had such a wonderful stay at Steves place. The setting is beautiful and we were so lucky with the weather. My sister and I stayed with our 4 kids and there was so much outdoor space for them to play and it's great having all the animals around. The house was clean and hot tub nice and hot which you don't always get staying in these places. What really made this place so good was the host. From.the moment we arrived Steve made us feel like he really wanted us to enjoy ourselves and he was so friendly, chilled and helpful throughout our stay. We tried to stay longer but unfortunately it was booked up. We would definitely book again.

charming 2 bed cottage located on small farm
Simon communicated well with us and made sure we settled in. Nice location for our stay and perfect for the two of us and child who loved seeing the chickens on the farm.

Idyllic and stylish private cottage by the stream
We had a wonderful weekend at Emma’s place. The location is very picturesque. We loved walking along the stream & river. The location was peaceful with a secluded & secure garden. The house was spotless and spacious - perfect for our family of 5. We all slept very well in the comfy beds and the house had everything we needed when travelling with young children - from plates, cups, bath toys, books, stair gate and cot. 2 nights wasn’t long enough so I hope we’ll be back.

Autumn Cottage
This was our 2nd stay at Autumn Cottage and it was as good as we remembered. A great space for 2 people. The village pub is a couple of doors along the road and the owners and other customers are very friendly and were more than willing to offer recommendations of places to visit in the area. If we come back to this part of Yorkshire we would definitely stay here again

Cargate Cottage
Fantastic place in a great location would highly recommend

Secluded rural 2 bedroom cottage near York
Had a brilliant stay. Very beautiful property. My little girls had a fantastic time playing in the vast strerch of private green space near the property. Claire is vey welcoming and very responsive. She helps even with small items like having a football for my little ones to play. Claire have a fantastic knowledge of the local area. Looking forward to book again.

Hudson Cottage - Chapel Row
Right from the start Sheena and her family were very welcoming and helpful. The cottage was lovely and in a fabulous location. Speaking to other guests leaving rhe cottage next door, I said I would love to return here. They told me that this was their 15th time staying, and I can totally understand. I can't wait to come back to Chapel Row Cottages.
Quick stats about cottage rentals in Helmsley
Total rentals
20 properties
Nightly prices starting at
£90 before taxes and fees
Total number of reviews
700 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Yorkshire Dales national park
- Flamingo Land Resort
- Harewood House
- Durham Cathedral
- North Yorkshire Water Park
- Fountains Abbey
- Royal Armouries Museum
- York Castle Museum
- Scarborough Beach
- The Bowes Museum
- Saltburn Beach
- Locomotion
- Cayton Bay
- Scarborough South Cliff Golf Club
- Filey Beach
- National Railway Museum
- Hartlepool Sea Front
- Malham Cove
- Studley Royal Park
- Ryedale Vineyards
- York Art Gallery
- Ganton Golf Club
- Whitby Beach