Photo by Mark Sage

Helmsley Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Helmsley vacation rentals

Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cliff House

Cottage in York

Cliff House
3.5 star property
The price is ₩834,525
₩1,001,430 total
includes taxes & fees
Dec 29 - Dec 30
Cliff House
Cottage | Interior
Ivy Cottage

Cottage in York

Ivy Cottage
3.5 star property
The price is ₩674,810
₩809,772 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Ivy Cottage
Cottage | Interior
29 Bondgate

Cottage in York

29 Bondgate
3.5 star property
The price is ₩800,819
₩960,983 total
includes taxes & fees
Jan 3 - Jan 4, 2026
29 Bondgate
Studio | Property grounds
Luxury Studio Cottage at Foot of Yorkshire Wolds

Apartment in York

Luxury Studio Cottage at Foot of Yorkshire Wolds
3.0 star property
10.0 out of 10, Exceptional, (2)
"This is a lovely place to stay.."
United Kingdom
Darren
The price is ₩311,609
₩467,559 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury Studio Cottage at Foot of Yorkshire Wolds
Apartment, Ensuite | Lounge
Churchill Apartments

Apartment in Bootham

Churchill Apartments
3.5 star property
8.6 out of 10, Excellent, (43)
"Very nice and close to everything. "
United States
Leah
The price is ₩251,953
₩302,344 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Churchill Apartments
Apartment, 3 Bedrooms, Patio | Living area | Flat-screen TV, DVD player
Riverbank View

Apartment in The Groves

Riverbank View
4.0 star property
10.0 out of 10, Exceptional, (25)
"Great location, lovely owners and a lovely place to stay 👍"
United Kingdom
chris
Riverbank View
Apartment, 2 Bedrooms (Triple Sleeper Bunk Bed) | 2 bedrooms, memory foam beds, soundproofing, iron/ironing board
Apartment 32

Apartment in Clifton

Apartment 32
3.5 star property
9.4 out of 10, Exceptional, (13)
"O apartamento é excelente, muito bom pra estadia da nossa família de cinco pessoas. É central, as camas são boas e, embora tenha apenas um banheiro, como estávamos em família atendeu bem. Apenas dois pontos que não gostei: aqui na descrição constava que havia lavanderia, no entanto, coloquei umas roupas pra lavar e elas não secaram, pois a máquina era apenas lavadora. Outro ponto q não gostei foi o horário do check out, 10 horas. Se tivesse visto isso não teria reservado. Mas de resto o...
Brazil
Juliana
The price is ₩255,204
₩306,244 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Apartment 32
Interior
18 Horner Street York

Vacation Home in Clifton

18 Horner Street York
3.0 star property
9.2 out of 10, Wonderful, (9)
"her and dryer, the coffee machine was definitely a wonderful bonus in the morning. Would definitely stay again "
Australia
Christina
18 Horner Street York
Premium bedding, individually decorated, individually furnished
Morndyke Shepherds' Huts

Cabin in Thirsk

Morndyke Shepherds' Huts
3.5 star property
9.8 out of 10, Exceptional, (19)
"Amazing place, thanks so much ! "
United Kingdom
Tom
Morndyke Shepherds' Huts
Flat-screen TV
The Old Dairy

Cottage in Thirsk

The Old Dairy
3.0 star property
10.0 out of 10, Exceptional, (1)
"Good experience "
United States
Todd
The price is ₩679,858
₩815,830 total
includes taxes & fees
Dec 28 - Dec 29
The Old Dairy
View from property
Goodramgate Apartments

Apartment in York

Goodramgate Apartments
4.0 star property
9.0 out of 10, Wonderful, (285)
"Very cute and charming apartment- lots of character. Plenty of space and good location. "
United States
Ashley
The price is ₩151,991
₩182,381 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Goodramgate Apartments
Exterior
Old Mill Tiny Homes

Aparthotel in Yarm

Old Mill Tiny Homes
2.0 star property
The price is ₩195,060
₩234,072 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Old Mill Tiny Homes
Bar (on property)
Station Suites

Aparthotel in Middlesbrough

Station Suites
4.0 star property
9.6 out of 10, Exceptional, (19)
"My stay was beautiful,clean environment"
United Kingdom
Yemi
The price is ₩134,972
₩161,966 total
includes taxes & fees
Dec 26 - Dec 27
Station Suites
Studio | Dining
Welbury Studio Retreat

Apartment in Northallerton

Welbury Studio Retreat
3.0 star property
9.0 out of 10, Wonderful, (2)
"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 ₩128,610
₩154,332 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Welbury Studio Retreat
Luxury Apartment, Ensuite (23) | Lounge
King's 23

Apartment in City Centre

King's 23
3.5 star property
10.0 out of 10, Exceptional, (22)
"Brilliant place to stay, everything you could need in a great location."
United Kingdom
Anonymous traveler
The price is ₩353,759
₩544,486 total
includes taxes & fees
Dec 27 - Dec 28
King's 23
Superior Cottage, 2 Bedrooms (Mustard) | Iron/ironing board, free WiFi, bed sheets
Craven Garth Cottages

Cottage in Pickering

Craven Garth Cottages
3.0 star property
9.4 out of 10, Exceptional, (46)
"Really nice place,friendly landlord and very helpful"
United Kingdom
Corin
The price is ₩373,865
₩448,638 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Craven Garth Cottages
Cottage | Interior
5 Church View

Cottage in Pickering

5 Church View
3.5 star property
10.0 out of 10, Exceptional, (1)
The price is ₩557,483
₩668,980 total
includes taxes & fees
Dec 28 - Dec 29
5 Church View
Studio | Dining
Courtyard Rooms - Studio - Double Bed - Wifi

Apartment in Northallerton

Courtyard Rooms - Studio - Double Bed - Wifi
3.0 star property
8.0 out of 10, Very Good, (2)
"Very friendly reception from the landlord Gareth who provided a most enlivening atmosphere in the Duke of Wellington ie a darts match for the men and Easter wreath making for the ladies. No food unfortunately but we found an excellent Italian restaurant in nearby Northallerton. The courtyard room was clean and comfortable, marred only by a very awkward shower - not easy to enter, due to lack of space."
United Kingdom
Alison
The price is ₩154,332
₩154,332 total
includes taxes & fees
Jan 15 - Jan 16, 2026
Courtyard Rooms - Studio - Double Bed - Wifi
Luxury Apartment, Ensuite (The Workshop) | Restaurant
The Workshop

Apartment in Bootham

The Workshop
2.0 star property
The price is ₩443,762
₩532,514 total
includes taxes & fees
Jan 3 - Jan 4, 2026
The Workshop
Cottage | Interior
Brook Cottage

Cottage in York

Brook Cottage
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely very very clean lovely owners and very helpful brilliant location and views "
United Kingdom
Laine
The price is ₩741,045
₩889,254 total
includes taxes & fees
Dec 28 - Dec 29
Brook Cottage
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

10/10 Excellent
"Great stay. The room was clean and quiet, comfy bed. "
Rachel 2-night trip
Posted 3 days ago
The Golden Fleece Hotel, Thirsk, North Yorkshire

Find out more about Helmsley

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

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

Yes, we give you a choice of vacation rentals close to well known local attractions in Helmsley, or you can select a secluded option if you want a relaxing place to 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 vacation home rentals that Helmsley has to offer?

Vas's York House: Visitors like this Helmsley vacation home rental. It 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 5 Expedia vacation rentals, you're sure 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 Duncombe Park and Hemsley Walled Garden.

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.