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Compare 185 Vacation Homes in Helmsley with updated reviews, rates, and availability.

Cottage in village location with lovely views to the Hambleton Hills and White H

9.8 out of 10, Exceptional, (83)
"The property was lovely, communication was great "
Cottage in village location with lovely views to the Hambleton Hills and White H

Host Stay Park View

2.0 star property
8.0 out of 10, Very Good, (3)
"After been there twice the communication is poor both times I questioned if there was an iron and nothing so I had to buy one "
Host Stay Park View

Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

9.8 out of 10, Exceptional, (27)
"We booked two barns to celebrate New Year and my retirement with family. It was a really large space for us all. We had a great stay. Only downside was the barns need a bit of updating. Otherwise perfect for us all."
Converted farmstead that sleeps 26; 6 showers, 2 baths;table tennis; sauna; gym.

Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

10.0 out of 10, Exceptional, (161)
"Lovely cottage, well appointed. Good base for lots of day trips. "
Rural peace & luxury near Malton, beautiful barn, stunning views, woodburner

Host Stay Fawcett Cottage

3.0 star property
Host Stay Fawcett Cottage

Host Stay Grange Cottage

2.0 star property
Host Stay Grange Cottage

Spacious period property on historic, private estate with seasonal, outdoor pool

10.0 out of 10, Exceptional, (50)
"A wonderful weekend, the perfect house, spacious, well equipped, spotless, and a lovely welcome basket of goodies and a birthday balloon-so thoughtful. Perfectly situated for a quiet weekend and easy access to York and local tourist spots. We had a lovely time, thank you."
Spacious period property on historic, private estate with seasonal, outdoor pool

Luxury retreat for 2 couples/ family in spectacular location in North York Moors

10.0 out of 10, Exceptional, (33)
"We had a fabulous time over NewYear in this lovely, cosy, warm & well-equipped property. Hosts were very welcoming. Fabulous views and lovely walks nearby and a trip into Whitby just a short drive away. A beautiful snow covered landscape on our final day. "
The price is AED 557
AED 1,717 total
includes taxes & fees
17 Mar - 18 Mar
Luxury retreat for 2 couples/ family in spectacular location in North York Moors

Luxury Barn Nr York with Sauna, ideal for families, friends up to 8 guests

10.0 out of 10, Exceptional, (112)
"Beautiful place, and location"
Luxury Barn Nr York with Sauna, ideal for families, friends up to 8 guests

Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

10.0 out of 10, Exceptional, (7)
"Gorgeous barb conversion. Not far from Whitby. View is amazing. Emma and Chris are lovely with a beautiful family. Recommended to friends who are going to book. Thank you for having us"
Dorm cottage for walkers/cyclists in North York Moors close to Whitby & coast

Host & Stay | Silton Hall

8.0 out of 10, Very Good, (5)
"We loved everything about this property! It was perfect for our large group. The pool was a huge hit. The rooms and bathrooms were brilliant and perfectly stocked with bedding and towels "
Host & Stay | Silton Hall

18 Horner Street York

3.0 star property
9.2 out of 10, Wonderful, (9)
"Last minute booking as decided to stay overnight in York. Communication for check in was quick, property was easy to find, close to town and super clean and tidy. Had a relaxing stay and would definitely consider again next time we were in York. Small supermarket and Mrs Greedy’s at end of road was excellent for supplies and a quick cooked breakfast. "
The price is AED 910
AED 1,092 total
includes taxes & fees
16 Mar - 17 Mar
18 Horner Street York

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

10.0 out of 10, Exceptional, (70)
"This was just perfect! The house was well stocked including the kitchen and the location could not have been better. It was so lovely just to walk through the church yard to the pub for dinner. I would highly recommend and we will def. be back!!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi

9.6 out of 10, Exceptional, (8)
"Always a pleasure to deal with the host and stay at this lovely cottage. Will be back for certain."
Beautiful 3 bedroom Cottage in Haxby, 5 miles from York, Parking, Free Wifi

No. 10 West End Osmotherley

9.6 out of 10, Exceptional, (40)
"Great location, excellent place to stay. Couldn't be happier. Would consider staying there again if in the area. Only thing we could have done more of is kindling for the fire but that's a very, very minor thing compared to all the many positives"
No. 10 West End Osmotherley

SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool

10.0 out of 10, Exceptional, (20)
"Such a historic venue, so peaceful if a bit remote. 5-10 minutes to get to the main road. Easy to find though, postcode satnav takes you right to the property with well signed directions when there. The property and grounds were immaculate, added bonus of an outside plug at parking to trickle charge an electric vehicle. "
SINGLE STOREY Four Superking en suite rooms on Red House Estate w/seasonal pool

Host & Stay | Greengate Cottage

9.2 out of 10, Wonderful, (25)
"Super property with all we needed. Comfortable and clean. Domestic essentials were provided, mot the case in many properties, but tea coffee and milk as well as washing up and dish washer kit. One of the prettiest villages in NYNNP with a pub, tea rooms and a great rural museum"
Host & Stay | Greengate Cottage

Host & Stay | Rose Cottage

9.6 out of 10, Exceptional, (4)
"Property was very clean and had all the facilities required for a pleasant stay. Booking of property was confusing due to both parties offering damage waivers - started the stay off on wrong foot as paid both. Although, the property itself helped dilute this additional payment."
Host & Stay | Rose Cottage

Charming 2 bed pet friendly sleeps 6 in Norton

10.0 out of 10, Exceptional, (1)
"Visiting friends locally and this ideal for that."
The price is AED 323
AED 727 total
includes taxes & fees
3 Apr - 4 Apr
Charming 2 bed pet friendly sleeps 6 in Norton

NEW with Vrbo! Stunning 1 bed barn conversion in beautiful rural village

10.0 out of 10, Exceptional, (1)
"Charlie's Barn is a gem of a find. This was exactly what we were looking for. Just under 12 miles from York so it was convenient for us to visit our son at the University. The barn itself was tastefully decorated, had all we needed for a comfortable stay. The location was ideal as a base to explore other areas in North Yorkshire. It was dog-friendly, a plus point for us, and we loved the fact that it had a little enclosed courtyard for our dog to go outside securely. The hosts were friendly and...
NEW with Vrbo! Stunning 1 bed barn conversion in beautiful rural village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Helmsley

Rye Court Cottages sleeps 20

10.0 out of 10, Exceptional, (1)
"Very good locstion. Agents very very pleasant"
Rye Court Cottages sleeps 20

Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

10.0 out of 10, Exceptional, (70)
"This was just perfect! The house was well stocked including the kitchen and the location could not have been better. It was so lovely just to walk through the church yard to the pub for dinner. I would highly recommend and we will def. be back!!"
Spacious House 3 ensuite bedrooms, sleeps 6, Centre of Helmsley, Pet friendly,

The Old Post Office - Central Helmsley with parking

8.0 out of 10, Very Good, (1)
"Great location"
The Old Post Office - Central Helmsley with parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.