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

Helmsley Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Helmsley holiday rentals

Interior

1. Ivy Cottage

Ivy Cottage
4.0 star property
York
The price is S$884
includes taxes & fees
3 Oct - 4 Oct
Ivy Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

2. Cliff House

Cliff House
3.5 star property
York
The price is S$879
includes taxes & fees
1 Oct - 2 Oct
Cliff House
Interior

3. 29 Bondgate

29 Bondgate
3.5 star property
York
The price is S$858
includes taxes & fees
9 Oct - 10 Oct
29 Bondgate
Fridge, dishwasher, electric kettle, toaster

4. 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 S$497
includes taxes & fees
2 Oct - 3 Oct
Lilac Cottage
Exterior

5. 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, (157 reviews)
"Everything was wonderful and amazing ill definetly be coming back "
United Kingdom
steffan
The price is S$97
includes taxes & fees
4 Oct - 5 Oct
The Little Hide - Adult Only Camping Pods
Interior

6. Middlesbrough Lodge

Middlesbrough Lodge
Middlesbrough
The price is S$80
includes taxes & fees
1 Oct - 2 Oct
Middlesbrough Lodge
Exterior

7. 5m xl Bell Tent With log Burner, Near Whitby

5m xl Bell Tent With log Burner, Near Whitby
3.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1 review)
"What a lovely place, we hired a beautiful Bell tent for 2 nights. It was set up with all the essentials on our arrival. The plot had plenty of space around to set up bbq room and room for kids to play. The site, washrooms and kitchen were like new, very well maintained regularly cleaned. I have a pet allergy so the no pets policy was a great bonus here for me too. We had a great time and will book again. Thank you. "
United Kingdom
Jenna
The price is S$122
includes taxes & fees
20 Sept - 21 Sept
5m xl Bell Tent With log Burner, Near Whitby
Exterior

8. Ceilidh Cottage

Ceilidh Cottage
3.5 star property
York
10.0 out of 10, Exceptional, (14 reviews)
"Lovely property in a lovely village - central to visit lots of interesting places."
United Kingdom
Barbara
The price is S$340
includes taxes & fees
24 Sept - 25 Sept
Ceilidh Cottage
Fridge, dishwasher, electric kettle, toaster

9. 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 S$1,069
includes taxes & fees
20 Sept - 21 Sept
Temple Hill View
1 bedroom, in-room safe, desk, iron/ironing board

10. CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.0 out of 10, Very good, (17 reviews)
"Budget room. Above average quality"
United Kingdom
Brian
The price is S$97
includes taxes & fees
30 Sept - 1 Oct
CoStays Aparthotel - Middlesbrough
Bar (on property)

11. Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (65 reviews)
"good parking, good breakfast, perfect for the train station, good size rooms"
United Kingdom
Alan
The price is S$140
includes taxes & fees
18 Oct - 19 Oct
Station Suites
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
"The hotel was in a nice location, the reception staff check-in was easy and friendly the hotel And bedrooms were very clean. Had dinner in the restaurant in the evening was of a high standard and very enjoyable. Breakfast fluffy style in the morning very nice too."
Steven 1-night trip
Posted 3 hours ago
Burn Hall Hotel

Frequently asked questions

Can I find holiday rentals in Helmsley?

Yes, there are holiday rentals in Helmsley close to Helmsley Arts Centre, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Helmsley has to offer?

Vas's York House: This holiday home rental outside of Helmsley is equipped with a garden, daily housekeeping and free WiFi to help you feel comfortable during your stay.

How many holiday rentals will I find in Helmsley?

With 7 Expedia holiday rentals, you're guaranteed 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 North York Moors National Park and Duncombe Park.

What are holiday rentals like in Helmsley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Helmsley. Holiday rentals feature extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip.