Search Holiday Rentals in Helmsley

  • 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
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Helmsley holiday rentals

Cottage | Interior

Cottage in York

Ivy Cottage
3.5 star property
The price is ฿14,226
฿17,071 total
includes taxes & fees
3 Mar - 4 Mar
Ivy Cottage
Cottage | Interior

Cottage in York

29 Bondgate
3.5 star property
The price is ฿17,197
฿20,636 total
includes taxes & fees
3 Mar - 4 Mar
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cottage in York

Cliff House
3.5 star property
The price is ฿17,616
฿21,139 total
includes taxes & fees
3 Mar - 4 Mar
Cliff House
Cottage | Interior

Cottage in Middlesbrough

Weavers Cottage
3.5 star property
The price is ฿31,877
฿38,252 total
includes taxes & fees
5 Mar - 6 Mar
Weavers Cottage
House | 3 bedrooms

Holiday Home in Middlesbrough

Host Stay Finch House
2.0 star property
The price is ฿15,126
฿19,354 total
includes taxes & fees
1 Mar - 2 Mar
Host Stay Finch House
Superior Room, 1 Double Bed (Double Studio) | 1 bedroom, in-room safe, desk, iron/ironing board

Apartment in Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
7.4 out of 10, Good, (3 reviews)
"The hotel was still being built on arrival. I had not been sent any instructions on how to access the building so could not get in for the first hour. When I left my room during the afternoon and returned, workers from the hotel were in my room removing a fridge. They accepted they should have checked with me first but this meant I left the hotel a night early as I did not feel safe in my room."
United Kingdom
Joanne
The price is ฿1,718
฿2,061 total
includes taxes & fees
15 Mar - 16 Mar
CoStays Aparthotel - Middlesbrough
Premium bedding, individually decorated, individually furnished

Cabin in Thirsk

Morndyke Shepherds' Huts
3.5 star property
9.8 out of 10, Exceptional, (20 reviews)
"Lovely place to stay, very relaxing"
United Kingdom
John
Morndyke Shepherds' Huts
Luxury Apartment, Ensuite (The Workshop) | Restaurant

Apartment in Bootham

The Workshop
2.0 star property
The price is ฿7,305
฿8,766 total
includes taxes & fees
1 Mar - 2 Mar
The Workshop
Exterior

Aparthotel in Yarm

Old Mill Tiny Homes
2.0 star property
The price is ฿5,348
฿6,417 total
includes taxes & fees
2 Mar - 3 Mar
Old Mill Tiny Homes
Studio | Dining

Apartment in Northallerton

Wellington Studio Retreat in Northallerton
3.0 star property
The price is ฿2,212
฿2,655 total
includes taxes & fees
1 Mar - 2 Mar
Wellington Studio Retreat in Northallerton
Bar (on property)

Aparthotel in Middlesbrough

Station Suites
4.0 star property
9.4 out of 10, Exceptional, (28 reviews)
"The staff was very friendly and responsive. Location is great - right across from the Middlesbrough train station."
United States
Brett
The price is ฿2,973
฿3,567 total
includes taxes & fees
5 Mar - 6 Mar
Station Suites
Interior

Holiday Home in Clifton

18 Horner Street York
3.0 star property
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
18 Horner Street York
Cottage | Interior

Cottage in Whitby

Westonby Lodge
3.5 star property
The price is ฿24,537
฿29,444 total
includes taxes & fees
13 Mar - 14 Mar
Westonby Lodge
Apartment | 2 bedrooms, Internet

Apartment in Saltburn-by-the-Sea

Host Stay The Surfer s Loft Apartment
2.0 star property
10.0 out of 10, Exceptional, (1 review)
Host Stay The Surfer s Loft Apartment
Penthouse (Tower Mews) | Living area | 35-inch flat-screen TV with digital channels, LCD TV

Apartment in York

Goodramgate Apartments
4.0 star property
9.0 out of 10, Wonderful, (289 reviews)
"Location is close to many sights in York. Enjoyed the stay"
United States
Paul
The price is ฿3,089
฿3,707 total
includes taxes & fees
1 Mar - 2 Mar
Goodramgate Apartments
2 bedrooms, individually decorated, individually furnished, free WiFi

Cottage in Holgate

202 Salisbury Terrace
3.0 star property
The price is ฿21,461
฿25,753 total
includes taxes & fees
7 Mar - 8 Mar
202 Salisbury Terrace
Apartment, 3 Bedrooms, Patio | Living area | Flat-screen TV, DVD player

Apartment in The Groves

Riverbank View
4.0 star property
10.0 out of 10, Exceptional, (25 reviews)
"Great location, lovely owners and a lovely place to stay 👍"
United Kingdom
chris
Riverbank View
Room, Shared Bathroom (Dog Pod) | Exterior

Apartment in York

The Little Hide - Adult Only Camping Pods
2.0 star property
9.2 out of 10, Wonderful, (149 reviews)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
United Kingdom
Michael
The price is ฿2,097
฿2,517 total
includes taxes & fees
1 Mar - 2 Mar
The Little Hide - Adult Only Camping Pods
Exterior

Cottage in Pickering

Bute Cottage
3.0 star property
The price is ฿23,418
฿28,102 total
includes taxes & fees
13 Mar - 14 Mar
Bute Cottage
Studio | Property grounds

Apartment in York

Luxury Studio Cottage at Foot of Yorkshire Wolds
3.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"This is a lovely place to stay.."
United Kingdom
Darren
The price is ฿6,700
฿10,054 total
includes taxes & fees
2 Mar - 3 Mar
Luxury Studio Cottage at Foot of Yorkshire Wolds
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

Dean Court Hotel

Dean Court Hotel

10/10 Excellent
"V friendly staff, room was lovely, very easy check in, would stay again "
Alistair 1-night trip
Posted 2 days ago
Dean Court Hotel

Find out more about Helmsley

Search for holiday rentals in Helmsley on Expedia! 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 close to the most popular sights in Helmsley, 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 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Helmsley stay.

What can I see and do in Helmsley?

Howardian Hills and North York Moors National Park 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 Hemsley Walled Garden.

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.