Vacation rentals in Helmsley

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Popular amenities for Helmsley vacation rentals

Other great vacation rentals in Helmsley

Top guest favorite
A freestanding roll-top bath is positioned against a charming panelled wall in muted tones. A vintage-style faucet complements the bath, while a wire basket holds a towel and a book. Light is softly reflected off the smooth surfaces, creating a serene bathing environment.
Barn in Stearsby
5 out of 5 average rating, 44 reviews

Luxurious 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 favorite
The rustic stone exterior of Crossing Cottage features a prominent sign displaying the name in elegant lettering. Lush greenery and a serene meadow landscape can be seen in the background, enhancing the cottage's welcoming presence in the countryside.
Cottage in Helmsley
5 out of 5 average rating, 25 reviews

Romantic 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 favorite
A charming stone cottage is framed by vibrant red berries hanging from trees. The lush green lawn surrounds the cottage, enhancing its quiet appeal. A small patio is visible next to the entrance, bordered by natural stone, inviting outdoor relaxation.
Cottage in Laskill
4.82 out of 5 average rating, 79 reviews

Foxglove 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
A pair of chrome faucets with cross-shaped handles are positioned above a white sink. The sink features a chain plug for draining water, while textured wall tiles in a neutral color are visible in the background.
Cottage in Helmsley
4.8 out of 5 average rating, 20 reviews

Fox 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 favorite
An outdoor copper bath is positioned on a wooden deck, surrounded by autumn leaves. Beyond, a serene lake reflects the changing foliage, with trees lining its banks creating a natural border. Gentle wind chimes are visible, adding to the tranquil ambiance of the setting.
Cabin in Kennythorpe
5 out of 5 average rating, 56 reviews

Woodland 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 favorite
A charming stone cottage is nestled among lush greenery, surrounded by tall trees. Two white chairs are positioned outside the entrance, inviting relaxation. The traditional roof features rustic tiles, and a flowering shrub adds a touch of nature to the setting.
Guesthouse in Oldstead
5 out of 5 average rating, 80 reviews

Mill 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 favorite
Tiny home in Urra
4.97 out of 5 average rating, 79 reviews

Maltkiln 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 favorite
A charming stone cottage is presented, featuring a light blue front door and multiple windows framed by lush greenery. The entrance is accentuated by decorative plants, contributing to the inviting exterior that complements the surrounding natural landscape.
Cottage in Oswaldkirk
4.98 out of 5 average rating, 44 reviews

charming 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 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.

Destinations to explore

  1. Airbnb
  2. United Kingdom
  3. England
  4. North Yorkshire
  5. Helmsley