Helmsley Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Helmsley holiday rentals

Interior

29 Bondgate

29 Bondgate
3.5 star property
York
The price is RM2,234
RM2,681 total
includes taxes & fees
23 Apr - 24 Apr
29 Bondgate
Interior

Ivy Cottage

Ivy Cottage
3.5 star property
York
The price is RM1,848
RM2,218 total
includes taxes & fees
23 Apr - 24 Apr
Ivy Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
The price is RM2,288
RM2,746 total
includes taxes & fees
24 Apr - 25 Apr
Cliff House
Fridge, dishwasher, electric kettle, toaster

Lilac Cottage

Lilac Cottage
3.0 star property
York
The price is RM1,494
RM1,793 total
includes taxes & fees
24 Apr - 25 Apr
Lilac Cottage
Premium bedding, individually decorated, individually furnished

Morndyke Shepherds' Huts

Morndyke Shepherds' Huts
3.5 star property
Thirsk
9.8 out of 10, Exceptional, (20 reviews)
"Lovely place to stay, very relaxing"
United Kingdom
John
The price is RM634
RM761 total
includes taxes & fees
20 Apr - 21 Apr
Morndyke Shepherds' Huts
Dining

Welbury Studio Retreat

Welbury Studio Retreat
3.0 star property
Northallerton
9.0 out of 10, Wonderful, (2 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 RM282
RM338 total
includes taxes & fees
21 Apr - 22 Apr
Welbury Studio Retreat
Exterior

Old Mill Tiny Homes

Old Mill Tiny Homes
2.0 star property
Yarm
10.0 out of 10, Exceptional, (1 review)
"Spotlessly clean and so cosy Brilliant stay Lovely pub within walking distance "
United Kingdom
Caroline
The price is RM757
RM908 total
includes taxes & fees
20 Apr - 21 Apr
Old Mill Tiny Homes
1 bedroom, in-room safe, desk, iron/ironing board

CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.0 out of 10, Very good, (5 reviews)
"Room was lovely and spotless. A staff member also made sure we got into the building and room as we arrived late. Would highly recommend."
United Kingdom
Sam
The price is RM244
RM302 total
includes taxes & fees
1 May - 2 May
CoStays Aparthotel - Middlesbrough
1 bedroom

Host Stay The Lobster Pot

Host Stay The Lobster Pot
2.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (2 reviews)
"Great 1 night stay, very friendly host, spotlessly clean. Great location only a few minutes walk to nearest pub. "
United Kingdom
Vicky
The price is RM467
RM646 total
includes taxes & fees
22 Apr - 23 Apr
Host Stay The Lobster Pot
Interior

18 Horner Street York

18 Horner Street York
3.0 star property
Clifton
9.2 out of 10, Wonderful, (9 reviews)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
Australia
Christina
The price is RM1,042
RM1,251 total
includes taxes & fees
20 Apr - 21 Apr
18 Horner Street York
Interior

Dragonstone Lodge

Dragonstone Lodge
3.0 star property
Northallerton
10.0 out of 10, Exceptional, (1 review)
"We loved this property. The owners obviously have an eye for decor as it is a really stylish place and beautifully finished. We loved how peaceful the property was and the owners had thought of everything . We really appreciated the tea, coffee and milk after a 5 hour drive and the muffins, biscuits and crisps were a lovely touch. All the information you needed was in a folder and we visited lots of the places recommenced in it. It’s a fantastic property and we hope to stay there again."
United Kingdom
Mark
The price is RM1,208
RM1,449 total
includes taxes & fees
3 May - 4 May
Dragonstone Lodge
Exterior

Vas's York House

Vas's York House
2.0 star property
Clifton
8.0 out of 10, Very good, (2 reviews)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
The price is RM267
RM321 total
includes taxes & fees
20 Apr - 21 Apr
Vas's York House
Bar (on property)

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (35 reviews)
"This was my fourth stay at Station Suites. It's good value and the staff are helpful and friendly. The rooms are great and the beds are really comfortable. "
United Kingdom
Colin
The price is RM356
RM427 total
includes taxes & fees
24 Apr - 25 Apr
Station Suites
1 bedroom, laptop workspace, iron/ironing board

Costays Apartment Standard Double Studio

Costays Apartment Standard Double Studio
2.0 star property
Middlesbrough
The price is RM347
RM416 total
includes taxes & fees
1 May - 2 May
Costays Apartment Standard Double Studio
Fridge, electric kettle, toaster, cookware/dishes/utensils

Elm Tree Cottage

Elm Tree Cottage
3.0 star property
Thirsk
10.0 out of 10, Exceptional, (1 review)
"Elm tree cottage was the best stay I’ve had in Yorkshire , I visit often and by far the best place I’ve stayed the hosts were lovely and kind and was great to chat too! The location was perfect in a cute little village on a farm close to Thirsk and an easy drive to York. Providing the essentials for cooking and a cozy little cottage too! Would definitely recommend and look forward to returning in the future! "
United Kingdom
Kira
The price is RM1,485
RM1,782 total
includes taxes & fees
23 Apr - 24 Apr
Elm Tree Cottage
Dining

Wellington Studio Retreat in Northallerton

Wellington Studio Retreat in Northallerton
3.0 star property
Northallerton
The price is RM282
RM338 total
includes taxes & fees
21 Apr - 22 Apr
Wellington Studio Retreat in Northallerton
Living area

Riverbank View

Riverbank View
4.0 star property
The Groves
10.0 out of 10, Exceptional, (25 reviews)
"Great location, lovely owners and a lovely place to stay 👍"
United Kingdom
chris
The price is RM868
RM1,042 total
includes taxes & fees
21 Apr - 22 Apr
Riverbank View
View from property

Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (291 reviews)
"Clean and central to shops and other attractions. Comfortable bed and lovely big bathroom."
United Kingdom
Melissa
The price is RM372
RM447 total
includes taxes & fees
26 Apr - 27 Apr
Goodramgate Apartments
3 bedrooms

Host Stay Finch House

Host Stay Finch House
2.0 star property
Middlesbrough
The price is RM1,927
RM2,465 total
includes taxes & fees
21 Apr - 22 Apr
Host Stay Finch House
3 bedrooms, individually decorated, individually furnished, free WiFi

York House

York House
3.0 star property
Pickering
The price is RM2,211
RM2,654 total
includes taxes & fees
3 May - 4 May
York House
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Helmsley Hotel Reviews

The Golden Fleece Hotel, Thirsk, North Yorkshire

The Golden Fleece Hotel, Thirsk, North Yorkshire

6/10 Okay
"Our superior room was looking tired and we didn’t have all the amenities in our room that are described on this site ie slippers,robes,coffee maker,espresso - the listing needs to be updated as I believe we have been “missold” No lift and a lot of stairs to access our room Breakfast was not as good as expected - the cooked breakfast was poor, poached eggs were hard and there was only one choice of pastry on the continental buffet, only one choice of milk and only cubed sugar that you can’t sprinkle on cereal "
Jayne 2-night trip
Posted 1 hour ago
The Golden Fleece Hotel, Thirsk, North Yorkshire

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Helmsley using one of the methods below:

  • View our selection of featured holiday rentals in Helmsley
  • Use the map to find apartments and other holiday homes in the Helmsley neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Helmsley while they last

Look no further and take a look at our great range of rental properties in Helmsley!

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.