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

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

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 ￥90,591
￥108,709 total
includes taxes & fees
Jan 19 - Jan 20
Cliff House
Cottage | Interior
Ivy Cottage

Cottage in York

Ivy Cottage
3.5 star property
The price is ￥73,156
￥87,787 total
includes taxes & fees
Jan 19 - Jan 20
Ivy Cottage
Cottage | Interior
29 Bondgate

Cottage in York

29 Bondgate
3.5 star property
The price is ￥88,434
￥106,121 total
includes taxes & fees
Jan 11 - Jan 12
29 Bondgate
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
Apartment, Ensuite | Lounge
Churchill Apartments

Apartment in Bootham

Churchill Apartments
3.5 star property
8.6 out of 10, Excellent, (43)
"Nice flat, great view and location, convenient parking. Only drawback is the communal door between the flat and lift wouldn't open, so we had to use 3 flights of stairs to go through the garage every time."
United Kingdom
R
The price is ￥27,314
￥32,777 total
includes taxes & fees
Jan 18 - Jan 19
Churchill Apartments
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 ￥35,301
￥52,512 total
includes taxes & fees
Jan 10 - Jan 11
Luxury Studio Cottage at Foot of Yorkshire Wolds
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
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 ￥25,839
￥31,007 total
includes taxes & fees
Jan 15 - Jan 16
Apartment 32
Cottage | Interior
The Cow Byre

Cottage in Saltburn-by-the-Sea

The Cow Byre
3.0 star property
10.0 out of 10, Exceptional, (1)
"I loved it there will definitely be going back soon.. Lovely location in lovely countryside."
United Kingdom
Terry
The price is ￥62,551
￥75,061 total
includes taxes & fees
Jan 21 - Jan 22
The Cow Byre
Apartment | 2 bedrooms, Internet
Host Stay The Surfer s Loft Apartment

Apartment in Saltburn-by-the-Sea

Host Stay The Surfer s Loft Apartment
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ￥15,245
￥34,164 total
includes taxes & fees
Jan 8 - Jan 9
Host Stay The Surfer s Loft Apartment
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 ￥16,477
￥19,772 total
includes taxes & fees
Jan 13 - Jan 14
Goodramgate Apartments
Exterior
Old Mill Tiny Homes

Aparthotel in Yarm

Old Mill Tiny Homes
2.0 star property
The price is ￥18,016
￥21,619 total
includes taxes & fees
Jan 26 - Jan 27
Old Mill Tiny Homes
Bar (on property)
Station Suites

Aparthotel in Middlesbrough

Station Suites
4.0 star property
9.2 out of 10, Wonderful, (22)
"The staff was very friendly and responsive. Location is great - right across from the Middlesbrough train station."
United States
Brett
The price is ￥11,215
￥13,458 total
includes taxes & fees
Jan 8 - Jan 9
Station Suites
Room, Shared Bathroom (Dog Pod) | Exterior
The Little Hide - Adult Only Camping Pods

Apartment in York

The Little Hide - Adult Only Camping Pods
2.0 star property
9.2 out of 10, Wonderful, (148)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
United Kingdom
Michael
The price is ￥9,692
￥11,630 total
includes taxes & fees
Jan 18 - Jan 19
The Little Hide - Adult Only Camping Pods
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 ￥13,555
￥16,267 total
includes taxes & fees
Jan 12 - Jan 13
Welbury Studio Retreat
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 ￥65,966
￥79,159 total
includes taxes & fees
Jan 11 - Jan 12
5 Church View
Studio | 1 bedroom
Host Stay The Lobster Pot

Vacation Home in Saltburn-by-the-Sea

Host Stay The Lobster Pot
2.0 star property
10.0 out of 10, Exceptional, (2)
"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 ￥17,193
￥23,805 total
includes taxes & fees
Jan 8 - Jan 9
Host Stay The Lobster Pot
Exterior
Vas's York House

Vacation Home in Clifton

Vas's York House
2.0 star property
8.0 out of 10, Very Good, (2)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
The price is ￥9,691
￥11,630 total
includes taxes & fees
Jan 14 - Jan 15
Vas's York House
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 ￥16,097
￥16,097 total
includes taxes & fees
Jan 8 - Jan 9
Courtyard Rooms - Studio - Double Bed - Wifi
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

Impossible Motel

Impossible Motel

10/10 Excellent
"Rooms were insane, not Thor the faint hearted mind as very dark but really funky it your looking for something different. Perfect t location, Pink venue was stunning too. Would love to come back and check out the hot tub room next"
CARLA 1-night trip
Posted 18 hours ago
Impossible Motel

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 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?

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 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.