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Helmsley Holiday Rentals

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Check prices for these dates

Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Helmsley holiday rentals

Interior
Ivy Cottage

Ivy Cottage

Ivy Cottage
3.5 star property
York
The price is HK$3,480
HK$4,176 total
includes taxes & fees
15 Dec - 16 Dec
Ivy Cottage
Private kitchen
29 Bondgate

29 Bondgate

29 Bondgate
3.5 star property
York
The price is HK$4,192
HK$5,031 total
includes taxes & fees
15 Dec - 16 Dec
29 Bondgate
Fridge, dishwasher, electric kettle, cookware/dishes/utensils
Cliff House

Cliff House

Cliff House
3.5 star property
York
The price is HK$4,307
HK$5,169 total
includes taxes & fees
29 Dec - 30 Dec
Cliff House
1 bedroom
The Little Hide - Adult Only Camping Pods

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, (148)
"Excellent night away. Pods are quite close together but wasn't a problem for us. "
United Kingdom
Michael
The price is HK$477
HK$573 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Little Hide - Adult Only Camping Pods
Lobby lounge
Station Suites

Station Suites

Station Suites
4.0 star property
Middlesbrough
9.6 out of 10, Exceptional, (19)
"My stay was beautiful,clean environment"
United Kingdom
Yemi
The price is HK$735
HK$883 total
includes taxes & fees
14 Dec - 15 Dec
Station Suites
View from property
Goodramgate Apartments

Goodramgate Apartments

Goodramgate Apartments
4.0 star property
York
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 HK$812
HK$974 total
includes taxes & fees
11 Jan - 12 Jan 2026
Goodramgate Apartments
Premium bedding, individually decorated, individually furnished
Morndyke Shepherds' Huts

Morndyke Shepherds' Huts

Morndyke Shepherds' Huts
3.5 star property
Thirsk
9.8 out of 10, Exceptional, (19)
"Amazing place, thanks so much ! "
United Kingdom
Tom
Morndyke Shepherds' Huts
Property grounds
Luxury Studio Cottage at Foot of Yorkshire Wolds

Luxury Studio Cottage at Foot of Yorkshire Wolds

Luxury Studio Cottage at Foot of Yorkshire Wolds
3.0 star property
York
10.0 out of 10, Exceptional, (2)
"This is a lovely place to stay.."
United Kingdom
Darren
The price is HK$1,632
HK$2,458 total
includes taxes & fees
12 Jan - 13 Jan 2026
Luxury Studio Cottage at Foot of Yorkshire Wolds
TV, video games, Netflix, DVD player
Host & Stay | The Artists Pad

Host & Stay | The Artists Pad

Host & Stay | The Artists Pad
Saltburn-by-the-Sea
9.4 out of 10, Exceptional, (3)
"The property is in a great location, right in the centre of town and close to the beach. Comfy beds and plenty of space for us all. "
United States
Sarah F.
The price is HK$937
HK$1,562 total
includes taxes & fees
13 Dec - 14 Dec
Host & Stay | The Artists Pad
Iron/ironing board, free WiFi, bed sheets
Craven Garth Cottages

Craven Garth Cottages

Craven Garth Cottages
3.0 star property
Pickering
9.4 out of 10, Exceptional, (46)
"Really nice place,friendly landlord and very helpful"
United Kingdom
Corin
The price is HK$1,998
HK$2,397 total
includes taxes & fees
10 Jan - 11 Jan 2026
Craven Garth Cottages
Fridge, dishwasher, electric kettle, toaster
The Old Dairy

The Old Dairy

The Old Dairy
3.0 star property
Thirsk
10.0 out of 10, Exceptional, (1)
"Good experience "
United States
Todd
The price is HK$3,507
HK$4,208 total
includes taxes & fees
15 Dec - 16 Dec
The Old Dairy
1 bedroom, desk, travel cot, bed sheets
Host & Stay | The Lobster Pot

Host & Stay | The Lobster Pot

Host & Stay | The Lobster Pot
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (1)
"Lovely location. Convenient for parking and travelling by bus. "
United States
Jessica J.
The price is HK$812
HK$1,125 total
includes taxes & fees
16 Dec - 17 Dec
Host & Stay | The Lobster Pot
Exterior
Willow Cottage 4 bedroom Cosy stopover, dogs welcome

Willow Cottage 4 bedroom Cosy stopover, dogs welcome

Willow Cottage 4 bedroom Cosy stopover, dogs welcome
Thornton-le-Beans
10.0 out of 10, Exceptional, (4)
"A most comfortable bungalow in a delightful village. Host kind & welcoming & the bungalow is kept to a good standard. Recommend the Crosby Inn for a meal too. "
United Kingdom
Colin A.
The price is HK$2,031
HK$2,312 total
includes taxes & fees
4 Jan - 5 Jan 2026
Willow Cottage 4 bedroom Cosy stopover, dogs welcome
Private kitchen
Vas's York House

Vas's York House

Vas's York House
2.0 star property
Clifton
8.0 out of 10, Very good, (2)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
The price is HK$521
HK$625 total
includes taxes & fees
6 Jan - 7 Jan 2026
Vas's York House
Property grounds
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi

Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Holgate
8.8 out of 10, Excellent, (5)
"A great location for a weekend away in York. The property was spotless when we arrived and great communication from the owner. 25 minutes to walk into the centre of York, via the river path and free in street parking was a real bonus."
United Kingdom
Ian
The price is HK$834
HK$1,313 total
includes taxes & fees
18 Dec - 19 Dec
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Fridge, microwave, oven, stovetop
Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.

Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.

Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.
2.0 star property
Holgate
10.0 out of 10, Exceptional, (1)
"Absolutely brulliant property.. a home away from home"
United Kingdom
John
The price is HK$1,135
HK$1,873 total
includes taxes & fees
17 Dec - 18 Dec
Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.
Terrace/patio
Luxury couple's country retreat in spectacular location in the North York Moors

Luxury couple's country retreat in spectacular location in the North York Moors

Luxury couple's country retreat in spectacular location in the North York Moors
glaisdale
10.0 out of 10, Exceptional, (93)
"Property was immaculate. Mark and Moira.where amazing, went way over and above without being asked. We would recommend this wee star of a place to anyone. Views are amazing, and the peace and quiet, just wow. "
United Kingdom
Pau K.
The price is HK$969
HK$3,156 total
includes taxes & fees
15 Dec - 16 Dec
Luxury couple's country retreat in spectacular location in the North York Moors
Outdoor dining
Wellington Studio Retreat in Northallerton

Wellington Studio Retreat in Northallerton

Wellington Studio Retreat in Northallerton
3.0 star property
Northallerton
The price is HK$680
HK$817 total
includes taxes & fees
14 Dec - 15 Dec
Wellington Studio Retreat in Northallerton
Property grounds
Glendevon Cottage - Enjoy a short 2-night stay

Glendevon Cottage - Enjoy a short 2-night stay

Glendevon Cottage - Enjoy a short 2-night stay
Staithes
9.6 out of 10, Exceptional, (159)
"Lovely cottage , clean and fully equipped to meet needs. Lovely, relaxing outdoor seating area . "
United Kingdom
Tracey d.
The price is HK$703
HK$870 total
includes taxes & fees
22 Dec - 23 Dec
Glendevon Cottage - Enjoy a short 2-night stay
2 bedrooms, memory-foam beds, soundproofing, iron/ironing board
Apartment 32

Apartment 32

Apartment 32
3.5 star property
Clifton
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 HK$1,458
HK$1,750 total
includes taxes & fees
5 Jan - 6 Jan 2026
Apartment 32
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

Grantham Arms

Grantham Arms

10/10 Excellent
"All of it really-I stay in lots of hotels and nothing was a problem and everything was of the highest quality"
Doug 2-night trip
Posted 2 days ago
Grantham Arms

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
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  • 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!

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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 4 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.