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Winston Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Winston holiday rentals

Property grounds

The Summer Palace, Middleham

The Summer Palace, Middleham
Leyburn
The Summer Palace, Middleham
Outdoor dining

Teal Cottage

Teal Cottage
2.0 star property
Leyburn
10.0 out of 10, Exceptional, (1 review)
The price is HK$3,115
HK$3,738 total
includes taxes & fees
3 Jul - 4 Jul
Teal Cottage
Exterior

Teal Cottage, is in Middleham.

Teal Cottage, is in Middleham.
Leyburn
The price is HK$3,847
HK$3,847 total
includes taxes & fees
3 Jul - 4 Jul
Teal Cottage, is in Middleham.
Fireplace

King's Cottage rests in Bedale

King's Cottage rests in Bedale
Bedale
The price is HK$5,141
HK$5,141 total
includes taxes & fees
1 Jul - 2 Jul
King's Cottage rests in Bedale
Fireplace

Malt Shovel Cottage nr Bedale.

Malt Shovel Cottage nr Bedale.
Bedale
The price is HK$4,717
HK$4,717 total
includes taxes & fees
17 Jul - 18 Jul
Malt Shovel Cottage nr Bedale.
Exterior

Rosemary Cottage, Leyburn

Rosemary Cottage, Leyburn
Leyburn
The price is HK$7,412
HK$7,412 total
includes taxes & fees
1 Jul - 2 Jul
Rosemary Cottage, Leyburn
Property grounds

The Gatehouse, Middleham

The Gatehouse, Middleham
Leyburn
The price is HK$4,630
HK$4,630 total
includes taxes & fees
10 Jul - 11 Jul
The Gatehouse, Middleham
WiFi

The Chase - 30 Ayr Avenue, Richmond

The Chase - 30 Ayr Avenue, Richmond
Catterick Garrison
The price is HK$4,369
HK$4,369 total
includes taxes & fees
3 Jul - 4 Jul
The Chase - 30 Ayr Avenue, Richmond
Property grounds

Old Post Office, Marrick

Old Post Office, Marrick
Richmond
The price is HK$8,717
HK$8,717 total
includes taxes & fees
30 Jun - 1 Jul
Old Post Office, Marrick
Interior

Dog Friendly 3 Bed Swaledale Cottage in Yorkshire Dales | Sleeps 5 | River Valley Views | WiFi & Cen

Dog Friendly 3 Bed Swaledale Cottage in Yorkshire Dales | Sleeps 5 | River Valley Views | WiFi & Cen
Richmond
9.8 out of 10, Exceptional, (11 reviews)
"Very nice place"
United Kingdom
Damian
The price is HK$9,009
HK$9,009 total
includes taxes & fees
3 Jul - 4 Jul
Dog Friendly 3 Bed Swaledale Cottage in Yorkshire Dales | Sleeps 5 | River Valley Views | WiFi & Cen
Interior

A fantastic, spacious, holiday home which comfortably sleeps 12 guests and 2 well behaved

A fantastic, spacious, holiday home which comfortably sleeps 12 guests and 2 well behaved
Richmond
9.8 out of 10, Exceptional, (7 reviews)
" Loads of room for a family gathering. Small garden , local pub and cafe are excellent "
United Kingdom
Martin S.
The price is HK$13,252
HK$13,252 total
includes taxes & fees
1 Jul - 2 Jul
A fantastic, spacious, holiday home which comfortably sleeps 12 guests and 2 well behaved
Interior

Prospect House

Prospect House
3.5 star property
Leyburn
10.0 out of 10, Exceptional, (1 review)
"Nice big property in centre of Middleham - gateway to Wensleydale. Large rooms sleeping up to 6 and large social kitchen area. The gem is the garden offset from house which is a sun trap all day long, We were lucky with weather and made full use of this ! Recommended property."
United Kingdom
ANTHONY
The price is HK$3,854
HK$4,624 total
includes taxes & fees
1 Jul - 2 Jul
Prospect House
Outdoor dining

COWLINGS, woodburner, off-road parking, Low Row

COWLINGS, woodburner, off-road parking, Low Row
Richmond
The price is HK$5,228
HK$5,228 total
includes taxes & fees
1 Jul - 2 Jul
COWLINGS, woodburner, off-road parking, Low Row
Outdoor dining

Margaret's Cottage, Low Row

Margaret's Cottage, Low Row
Richmond
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our week in Low Row. The cottage is comfortable and well-equipped, and the view is one of the best anywhere! We hope to return soon."
United States
Jonathan G.
The price is HK$5,217
HK$5,217 total
includes taxes & fees
5 Jul - 6 Jul
Margaret's Cottage, Low Row
Smart TV

An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, WiFi & electric car charger

An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, WiFi & electric car charger
Richmond
10.0 out of 10, Exceptional, (9 reviews)
"Perfect cottage for 2, very well equipped, brilliant location with walks from the doorstep, lots of good pubs within walking distance, Dales bike Centre across the road served amazing food ( take away too if you wanted) would stay again"
United Kingdom
Helen F.
The price is HK$5,183
HK$5,183 total
includes taxes & fees
30 Jun - 1 Jul
An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, WiFi & electric car charger
Exterior

Beautiful, 2 bedroom, first floor apartment, at the heart of a busting Dales Village.

Beautiful, 2 bedroom, first floor apartment, at the heart of a busting Dales Village.
Richmond
9.8 out of 10, Exceptional, (10 reviews)
"A very warm and spotless apartment. Great place to base oneself for a relaxing weekend "
United States
Dennis N.
The price is HK$3,385
HK$3,385 total
includes taxes & fees
29 Jun - 30 Jun
Beautiful, 2 bedroom, first floor apartment, at the heart of a busting Dales Village.
Property grounds

Dog Friendly Cottage with Private Drive, Enclosed Garden, Central Heating, Free WiFi & pubs nearby

Dog Friendly Cottage with Private Drive, Enclosed Garden, Central Heating, Free WiFi & pubs nearby
Richmond
9.4 out of 10, Exceptional, (20 reviews)
"Great place to stay in a fantastic location will definitely return."
United Kingdom
Paul S.
The price is HK$6,441
HK$6,441 total
includes taxes & fees
30 Jun - 1 Jul
Dog Friendly Cottage with Private Drive, Enclosed Garden, Central Heating, Free WiFi & pubs nearby
Exterior

Low Cottage, a dog friendly holiday home for up to four people in the pretty village of Reeth.

Low Cottage, a dog friendly holiday home for up to four people in the pretty village of Reeth.
Richmond
10.0 out of 10, Exceptional, (12 reviews)
"Cosy cottage in fantastic, vibrant village. Would come again."
United Kingdom
Phil J.
The price is HK$4,959
HK$4,959 total
includes taxes & fees
29 Jun - 30 Jun
Low Cottage, a dog friendly holiday home for up to four people in the pretty village of Reeth.
Smart TV

A fantastic, 2 bed cottage, sleeping 4 people and 1 furry friend w/open fire, WiFi & central heating

A fantastic, 2 bed cottage, sleeping 4 people and 1 furry friend w/open fire, WiFi & central heating
Richmond
9.4 out of 10, Exceptional, (3 reviews)
"Lovely cottage, clean & had everything we needed for a comfortable stay."
United Kingdom
Alison S.
The price is HK$4,485
HK$4,485 total
includes taxes & fees
29 Jun - 30 Jun
A fantastic, 2 bed cottage, sleeping 4 people and 1 furry friend w/open fire, WiFi & central heating
Interior

A cosy stone cottage with stunning views, village charm, and adventure at your doorstep

A cosy stone cottage with stunning views, village charm, and adventure at your doorstep
Richmond
10.0 out of 10, Exceptional, (3 reviews)
"Lovely cottage in the perfect location. "
United Kingdom
Lucy
The price is HK$4,754
HK$4,754 total
includes taxes & fees
9 Jul - 10 Jul
A cosy stone cottage with stunning views, village charm, and adventure at your doorstep
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 Winston Hotel Reviews

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

10/10 Excellent
"All was really good and the staff were excellent"
David 1-night trip
Posted 3 hours ago
Parkmore Hotel & Leisure Club, Sure Hotel Collection by BW

Find out more about Winston

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Look no further and take a look at our great range of rental properties in Winston!

Frequently asked questions

Can I find holiday rentals in Winston?

Yes, there are holiday rentals close to the most popular sights in Winston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winston has to offer?

Pets - Parking - Patio - Wifi - Sleeps 4: This holiday home rental outside of Winston offers a private garden and free WiFi to help you feel comfortable in your new surroundings. Kitchen amenities include a fridge, an oven and a microwave.

What’s there to see and do in Winston?

While exploring the area, visit family-friendly sights like National Railway Museum at Shildon, or get outside and enjoy nature at Hamsterley Forest. In the wider area, you’ll find Raby Castle and Barnard Castle.

What’s a holiday rental in Winston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winston. Holiday rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.