Holiday Homes 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 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Helmsley holiday homes

Smart TV, offices

Beautiful stone cottage in the heart of Helmsley - sleeps 2

Beautiful stone cottage in the heart of Helmsley - sleeps 2
Helmsley
The price is NZ$1,284
includes taxes & fees
12 Feb - 13 Feb
Beautiful stone cottage in the heart of Helmsley - sleeps 2
Exterior

Vas's York House

Vas's York House
2.0 star property
Clifton
8.0 out of 10, Very good, (2 reviews)
"Clean room and bathroom, lovely and welcoming host"
United Kingdom
Breece
The price is NZ$114
includes taxes & fees
2 Feb - 3 Feb
Vas's York House
Smart TV

Entire house 🏠. suitable for families and workers.

Entire house 🏠. suitable for families and workers.
Middlesbrough
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and a good area"
United Kingdom
Marek
The price is NZ$286
includes taxes & fees
1 Feb - 2 Feb
Entire house 🏠. suitable for families and workers.
Studio

Host Stay The Lobster Pot

Host Stay The Lobster Pot
2.0 star property
Saltburn-by-the-Sea
10.0 out of 10, Exceptional, (2 reviews)
"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 NZ$255
includes taxes & fees
1 Feb - 2 Feb
Host Stay The Lobster Pot
Interior

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.
Holgate
10.0 out of 10, Exceptional, (1 review)
"Absolutely brulliant property.. a home away from home"
United Kingdom
John
The price is NZ$391
includes taxes & fees
8 Feb - 9 Feb
Free parking, 15 mins walk to Railway Museum and 30 mins walk to train station.
2 bedrooms, desk, iron/ironing board, travel cot

2 Bedroom House with Garden next to the River Tees

2 Bedroom House with Garden next to the River Tees
Stockton on Tees
10.0 out of 10, Exceptional, (2 reviews)
"Good location, host was very responsive, property had everything we needed. Good check-in/out process "
United Kingdom
David R.
The price is NZ$200
includes taxes & fees
8 Feb - 9 Feb
2 Bedroom House with Garden next to the River Tees
TV, fireplace

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
8.6 out of 10, Excellent, (9 reviews)
"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 NZ$287
includes taxes & fees
12 Feb - 13 Feb
Traditional & Cosy, Entire York Home near the City & River, Free Parking, WiFi
Fridge, microwave, oven, stovetop

The Great Ayton Hideaway

The Great Ayton Hideaway
Great Ayton
8.0 out of 10, Very good, (1 review)
"Did what it said on the tin"
United Kingdom
Nick L.
The price is NZ$257
includes taxes & fees
1 Feb - 2 Feb
The Great Ayton Hideaway
Dining

The Burton York 3 bedroom House sleeps 6

The Burton York 3 bedroom House sleeps 6
Clifton
10.0 out of 10, Exceptional, (1 review)
"Very comfortable."
United States
Evan
The price is NZ$598
includes taxes & fees
1 Feb - 2 Feb
The Burton York 3 bedroom House sleeps 6
Interior

Luxury retreat for 2 couples/ family in spectacular location in North York Moors

Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Glaisdale
10.0 out of 10, Exceptional, (42 reviews)
"Loved the location and the property was lovely. We would return again!"
United States
Cynthia T.
The price is NZ$841
includes taxes & fees
2 Mar - 3 Mar
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Fridge, microwave, oven, stovetop

Contemporary eco home with a twist!

Contemporary eco home with a twist!
Marton-in-Cleveland
The price is NZ$316
includes taxes & fees
10 Feb - 11 Feb
Contemporary eco home with a twist!
TV

Lockwood Cottage, Close to Monk Bar, sleeps 4

Lockwood Cottage, Close to Monk Bar, sleeps 4
The Groves
10.0 out of 10, Exceptional, (1 review)
"Perfect! Great place, clean and comfortable. Excellent location. Would highly recommend!"
United Kingdom
Sophie W.
The price is NZ$529
includes taxes & fees
11 Feb - 12 Feb
Lockwood Cottage, Close to Monk Bar, sleeps 4
Smart TV

Home and Away

Home and Away
Eaglescliffe
The price is NZ$282
includes taxes & fees
10 Feb - 11 Feb
Home and Away
Dining

Key worker short term accommodation - South View Billingham

Key worker short term accommodation - South View Billingham
Stockton-on-Tees
The price is NZ$324
includes taxes & fees
1 Feb - 2 Feb
Key worker short term accommodation - South View Billingham
Dining

Charming 3-bedroom house with WiFi and free parking within compound in Thornaby

Charming 3-bedroom house with WiFi and free parking within compound in Thornaby
Thornaby
The price is NZ$290
includes taxes & fees
10 Feb - 11 Feb
Charming 3-bedroom house with WiFi and free parking within compound in Thornaby
Cottage | Interior

Manor Cottage

Manor Cottage
4.0 star property
Pickering
The price is NZ$1,009
includes taxes & fees
9 Feb - 10 Feb
Manor Cottage
Fridge, microwave, oven, stovetop

2 Bedroom Riverside Property with Roof Terrace

2 Bedroom Riverside Property with Roof Terrace
Stockton On Tees
The price is NZ$218
includes taxes & fees
1 Feb - 2 Feb
2 Bedroom Riverside Property with Roof Terrace
Dining

The Dodsworth modern 4 bedroom house, sleeps 8

The Dodsworth modern 4 bedroom house, sleeps 8
York
9.0 out of 10, Wonderful, (2 reviews)
"Enjoyed our stay in this beautifully decorated, comfortable & clean house. Great location for getting into the city centre, ideal for our weekend break in the run-up to Christmas"
United Kingdom
Rachel G.
The price is NZ$732
includes taxes & fees
8 Feb - 9 Feb
The Dodsworth modern 4 bedroom house, sleeps 8
Dining

Nellie's Retreat - Luxury 3-Bed Pet Friendly Home in Guisborough

Nellie's Retreat - Luxury 3-Bed Pet Friendly Home in Guisborough
Guisborough
The price is NZ$386
includes taxes & fees
1 Feb - 2 Feb
Nellie's Retreat - Luxury 3-Bed Pet Friendly Home in Guisborough
2 bedrooms, iron/ironing board, travel cot, free WiFi

Cosy York Home with Parking - Pass the Keys

Cosy York Home with Parking - Pass the Keys
The Groves
10.0 out of 10, Exceptional, (2 reviews)
"The very best thing about this home is the location - it was so close to everything. We could walk everywhere we wanted to go. We loved sitting in the little courtyard. The owner left excellent instructions on how to operate the windows, etc. Would prefer to communicate directly with the owner, but Pass the Keys did a good job of responding."
United States
Helen G.
The price is NZ$600
includes taxes & fees
18 Feb - 19 Feb
Cosy York Home with Parking - Pass the Keys
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

Leonardo Hotel Middlesbrough

Leonardo Hotel Middlesbrough

10/10 Excellent
"Spacious room, good facilities, easy parking, nice breakfast "
Stuart 1-night trip
Posted 3 days ago
Leonardo Hotel Middlesbrough

Find out more about Helmsley

Helmsley Holiday Homes information

Number of reviews
58
Accommodation
235 Holiday Homes
Lowest Price
NZ$114
Highest Price
NZ$1,009