A medieval castle surrounded by a lush green landscape and a small village in the background.

Helmsley Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Helmsley vacation rentals

A sunlit room with large windows, wicker furniture, and a rug.

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is AED 1,684
AED 2,021 total
includes taxes & fees
3 Oct - 4 Oct
Ivy Cottage
A cozy living room with a fireplace, a television, and comfortable seating.

2. Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
"Very happy with our stay. The accommodation was just right for 2, in a really excellent location"
United States
Helen H.
The price is AED 1,696
AED 1,818 total
includes taxes & fees
30 Sep - 1 Oct
Beautiful stone cottage in the heart of Helmsley - sleeps 2
A modern living room with a fireplace, a television, a coffee table, and a sofa.

3. HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms

HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
HELMSLEY
HELMSLEY COTTAGE - sleeps 6 guests in 3 bedrooms
A modern kitchen with white cabinetry, a Bosch oven, and a coffee machine.

4. Eighteen Pottergate - Beautiful cottage with garden central location

Eighteen Pottergate - Beautiful cottage with garden central location
HELMSLEY
Eighteen Pottergate - Beautiful cottage with garden central location
A dining table set with white plates, silverware, and wine glasses, accompanied by a vase of flowers.

5. Cliff House

Cliff House
3.5 star property
York
The price is AED 2,086
AED 2,503 total
includes taxes & fees
4 Oct - 5 Oct
Cliff House
A stone building with a green door, a window with a white frame, and a small garden area with potted plants.

6. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is AED 2,035
AED 2,442 total
includes taxes & fees
9 Oct - 10 Oct
29 Bondgate
A compact kitchen with a washing machine, a sink, and a stove.

7. Lilac Cottage

Lilac Cottage
3.0 star property
York
9.0 out of 10, Wonderful, (2 reviews)
"Lovely cottage in a quiet village."
United States
Kevin
The price is AED 1,179
AED 1,414 total
includes taxes & fees
2 Oct - 3 Oct
Lilac Cottage
A campsite with two cabins, each with a wooden deck and outdoor seating.

8. The Little Hide - Adult Only Camping Pods

The Little Hide - Adult Only Camping Pods
2.0 star property
York
9.2 out of 10, Wonderful, (158 reviews)
"Highly recommend this place hidden Gem, great little quite spot"
United Kingdom
Steve
The price is AED 231
AED 277 total
includes taxes & fees
11 Oct - 12 Oct
The Little Hide - Adult Only Camping Pods
A cozy, wooden interior with a dining area, kitchen, and a sofa by a large window overlooking a grassy landscape.

9. Cosy Rural Cabin with Private Hot Tub

Cosy Rural Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (8 reviews)
"Lovely pods, great area, nice and safe for the kids, everything provided, owners took us to feed the animals, bbq a great bonus"
United States
Alex
The price is AED 870
AED 870 total
includes taxes & fees
5 Oct - 6 Oct
Cosy Rural Cabin with Private Hot Tub
A stone house with a tiled roof, surrounded by a well-maintained lawn and dense greenery.

10. Keldholme Cottage 1 - UK10992

Keldholme Cottage 1 - UK10992
Keldholme, near Kirkbymoorside
9.8 out of 10, Exceptional, (10 reviews)
"Excellent for get away from it all beautiful countryside and walks."
United States
John Kelly
The price is AED 1,214
AED 1,214 total
includes taxes & fees
21 Oct - 22 Oct
Keldholme Cottage 1 - UK10992
A bar area with a fireplace, stools, and a television screen displaying an outdoor scene.

11. Welbury Studio, Sleeps 2, Pet Friendly & Parking

Welbury Studio, Sleeps 2, Pet Friendly & Parking
3.0 star property
Northallerton
9.6 out of 10, Exceptional, (5 reviews)
"Very helpful, we were going to be later than anticipated arriving, phoned to let them know, they reassured us it was no problem, everything was ready for our stay. Check-in at the bar was easy, staff showed us to our studio, staff very cheerful. Food in the pub was great, not just pub grub. Only downside, studio was small."
United Kingdom
Gillian
The price is AED 241
AED 290 total
includes taxes & fees
6 Oct - 7 Oct
Welbury Studio, Sleeps 2, Pet Friendly & Parking
A staircase with white balusters, a door with a circular glass window, and a wall-mounted light fixture.

12. Middlesbrough Lodge

Middlesbrough Lodge
Middlesbrough
The price is AED 151
AED 210 total
includes taxes & fees
3 Oct - 4 Oct
Middlesbrough Lodge
A stone building with a steeply pitched roof, a narrow street, and a clear sky.

13. Heather Cottage - a beautiful cosy cottage

Heather Cottage - a beautiful cosy cottage
Snainton
10.0 out of 10, Exceptional, (1 review)
"Clean, organised flat in a lovely area. The hosts communication was great throughout, and there was a great guest book containing recommendations for the local area."
United Kingdom
Luigi
The price is AED 380
AED 550 total
includes taxes & fees
30 Sep - 1 Oct
Heather Cottage - a beautiful cosy cottage
A cozy, compact room with a loft bed, a small dining table, a bench, and a kitchenette.

14. Ensuite Family Cabin with Private Hot Tub

Ensuite Family Cabin with Private Hot Tub
Thirsk
10.0 out of 10, Exceptional, (4 reviews)
"This was such a fun experience. "
United States
Chantel
The price is AED 864
AED 864 total
includes taxes & fees
30 Sep - 1 Oct
Ensuite Family Cabin with Private Hot Tub
A patio with a table and chairs, surrounded by lush greenery and a wooden fence.

15. 1 bedroom accommodation in Slingsby, near Malton

1 bedroom accommodation in Slingsby, near Malton
Slingsby, near Malton
10.0 out of 10, Exceptional, (9 reviews)
"Lovely cottage. Welcoming and homely with everything provided that we needed. Good place for a relax and good walking for the dog."
United States
Carol Horne
The price is AED 1,807
AED 1,807 total
includes taxes & fees
8 Oct - 9 Oct
1 bedroom accommodation in Slingsby, near Malton
A two-story brick house with a bay window, a black front door, and satellite dishes on the roof.

16. Cosy, 2 Bedroom Cottage in Guisborough Town Centre

Cosy, 2 Bedroom Cottage in Guisborough Town Centre
North Yorkshire
10.0 out of 10, Exceptional, (2 reviews)
"It’s well situated and a nice place to stay. "
United States
jane
The price is AED 351
AED 428 total
includes taxes & fees
4 Oct - 5 Oct
Cosy, 2 Bedroom Cottage in Guisborough Town Centre
A modern kitchen with a built-in dishwasher, a microwave, and a stove. There is a window providing a view of the outdoors.

17. Temple Hill View

Temple Hill View
3.0 star property
York
10.0 out of 10, Exceptional, (1 review)
"The house was lovely, spacious, clean and well stocked with anything you might need. It is in a tranquil village and has plentiful off-road parking. The garden has an excellent view and is so peaceful to sit in. There is a park 2 minutes down the lane, a football field, and if you continue down the lane, there is a pond and a lovely walk around it. It was perfectly located between all the walking areas I wanted to see and complete. When we arrived there was bread, milk and some treats waiting...
United Kingdom
Jade
The price is AED 2,527
AED 3,032 total
includes taxes & fees
2 Oct - 3 Oct
Temple Hill View
A modern hotel room with a large bed, a balcony, and a view of the city at dusk.

18. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
7.8 out of 10, Good, (19 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is AED 230
AED 277 total
includes taxes & fees
12 Oct - 13 Oct
CoStays Aparthotel - Middlesbrough
A modern living room with a brown sofa, a wall-mounted light, and a sliding glass door leading to an outdoor area.

19. Foxtail Glamping Pod - sleeps 2 | Gold Award winning

Foxtail Glamping Pod - sleeps 2 | Gold Award winning
Pickering
10.0 out of 10, Exceptional, (9 reviews)
"The pods have everything you need it’s clean modern, outside is kept neat and tidy, so relaxing, would definitely recommend and would come back again"
United Kingdom
Joy
The price is AED 1,007
AED 1,007 total
includes taxes & fees
30 Sep - 1 Oct
Foxtail Glamping Pod - sleeps 2 | Gold Award winning
A kitchen with light green cabinets, a tiled backsplash, a stove, a toaster, and a window with a view of greenery.

20. Keldholme Cottages 2 - UK11488

Keldholme Cottages 2 - UK11488
Keldholme, near Kirkbymoorside
10.0 out of 10, Exceptional, (9 reviews)
"Lovely and cosy cottage. Ideal for holiday stay. We thoroughly enjoyed our stay there."
United States
Kevin Jones
The price is AED 1,421
AED 1,421 total
includes taxes & fees
4 Oct - 5 Oct
Keldholme Cottages 2 - UK11488
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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Top Helmsley Hotel Reviews

Burn Hall Hotel

Burn Hall Hotel

10/10 Excellent
"Very enjoyable stay. Very peaceful location. Excellent buffet breakfast. Will happily stay again in the future"
John 1-night trip
Posted 9 hours ago
Burn Hall Hotel

Frequently asked questions

Can I find vacation rentals in Helmsley?

Yes, we give you a choice of vacation rentals in Helmsley close to Helmsley Arts Centre, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors like the top-notch restaurants and spas in Helmsley. Make sure you have time to check out the parks while you're in the area.

What are some of the best vacation home rentals that Helmsley has to offer?

Vas's York House: You might want to consider this vacation home rental near Helmsley, which is equipped with a garden, daily housekeeping, and free WiFi to help you feel comfortable during your stay.

How many vacation rentals will I find in Helmsley?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Helmsley stay.

What can I see and do in Helmsley?

Hemsley Walled Garden and Howardian Hills are a couple of scenic spots to enjoy the outdoors, whereas Helmsley Arts Centre is one of the cultural attractions. Other places in town to visit include Helmsley Castle and North York Moors National Park.

What are vacation rentals like in Helmsley?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Helmsley. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for family gatherings.