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

Helmsley Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Helmsley vacation rentals

Interior

29 Bondgate

29 Bondgate
3.5 star property
York
The price is P34,490
P41,388 total
includes taxes & fees
Jul 22 - Jul 23
29 Bondgate
Interior

Ivy Cottage

Ivy Cottage
3.5 star property
York
The price is P41,080
P49,296 total
includes taxes & fees
Jul 17 - Jul 18
Ivy Cottage
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

Cliff House

Cliff House
3.5 star property
York
The price is P35,331
P42,398 total
includes taxes & fees
Aug 11 - Aug 12
Cliff House
Exterior

Baby Moon

Baby Moon
2.0 star property
Guisborough
9.6 out of 10, Exceptional, (10 reviews)
"Really good customer service, the yurt was very comfortable. Good sites nearby to drive to (not walking distance)."
United Kingdom
Anonymous traveler
The price is P9,390
P9,390 total
includes taxes & fees
Jul 12 - Jul 13
Baby Moon
Exterior

The Cabin

The Cabin
3.0 star property
Malton
The price is P26,358
P31,630 total
includes taxes & fees
Jul 18 - Jul 19
The Cabin
1 bedroom, in-room safe, desk, iron/ironing board

CoStays Aparthotel - Middlesbrough

CoStays Aparthotel - Middlesbrough
3.5 star property
Middlesbrough
8.6 out of 10, Excellent, (8 reviews)
"Very impressive amenities and so clean with a huge comfortable bed."
United Kingdom
emma
The price is P4,535
P5,760 total
includes taxes & fees
Jul 18 - Jul 19
CoStays Aparthotel - Middlesbrough
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 P6,446
P7,735 total
includes taxes & fees
Jul 12 - Jul 13
Costays Apartment Standard Double Studio
Bar (on property)

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.4 out of 10, Exceptional, (43 reviews)
"The property was really clean and the staff really friendly and helpful and a credit to the comoany"
United Kingdom
Sharon
The price is P5,505
P6,606 total
includes taxes & fees
Aug 2 - Aug 3
Station Suites
Exterior

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 P4,811
P5,773 total
includes taxes & fees
Jul 12 - Jul 13
The Little Hide - Adult Only Camping Pods
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 P10,516
P12,619 total
includes taxes & fees
Jul 13 - Jul 14
Old Mill Tiny Homes
Exterior

Ceilidh Cottage

Ceilidh Cottage
3.5 star property
York
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful cottage, family friendly. "
United Kingdom
Luca
The price is P17,182
P20,618 total
includes taxes & fees
Jul 16 - Jul 17
Ceilidh Cottage
View from property

Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
9.0 out of 10, Wonderful, (300 reviews)
"This is a fantastic space in an incredible location to visit York within the city walls. The room was clean and very comfortable. Would definitely stay here again. Monks loft."
Canada
Aaron
The price is P6,823
P8,188 total
includes taxes & fees
Jul 12 - Jul 13
Goodramgate Apartments
3 bedrooms

Host Stay Finch House

Host Stay Finch House
2.0 star property
Middlesbrough
The price is P34,992
P43,305 total
includes taxes & fees
Jul 14 - Jul 15
Host Stay Finch House
Interior

Pippin Cottage

Pippin Cottage
3.0 star property
Ripon
The price is P21,101
P25,321 total
includes taxes & fees
Jul 22 - Jul 23
Pippin Cottage
Dining

Welbury Studio Retreat

Welbury Studio Retreat
3.0 star property
Northallerton
9.4 out of 10, Exceptional, (3 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 P3,625
P4,350 total
includes taxes & fees
Jul 15 - Jul 16
Welbury Studio Retreat
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 P16,088
P19,306 total
includes taxes & fees
Jul 14 - Jul 15
18 Horner Street York
Lounge

Churchill Apartments

Churchill Apartments
3.5 star property
Bootham
8.8 out of 10, Excellent, (50 reviews)
"Lovely apartment, so close to York Minster and York central, but really quiet at night. Jamal was really helpful with check-in. Definitely will stay again."
United Kingdom
Sarah
Churchill Apartments
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 P12,646
P15,175 total
includes taxes & fees
Jul 12 - Jul 13
Riverbank View
Exterior

Minn's Cottage

Minn's Cottage
3.0 star property
Scarborough
The price is P22,129
P26,555 total
includes taxes & fees
Aug 9 - Aug 10
Minn's Cottage
Dining

Courtyard Rooms - Studio - Double Bed - Wifi

Courtyard Rooms - Studio - Double Bed - Wifi
3.0 star property
Northallerton
8.0 out of 10, Very Good, (2 reviews)
"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 P4,350
P4,350 total
includes taxes & fees
Jul 15 - Jul 16
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.
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Top Helmsley Hotel Reviews

Burn Hall Hotel

Burn Hall Hotel

10/10 Excellent
"Stayed on a very hot day so room was a bit warm but not too bad and everything else about the stay was good - can’t blame a hotel for the weather!!"
Trudi 1-night trip
Posted less than an hour ago
Burn Hall 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 vacation rentals in Helmsley?

Yes, we give you a choice of vacation rentals in Helmsley close to Helmsley Arts Centre, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 7 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 Cleveland Way.

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.