A group of people in canoes on a river.

Winston Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Winston vacation rentals

Balcony

1. Badgers Sett

Badgers Sett
3.5 star property
Darlington
$542 nightly
The price is $650
Sep 4 - Sep 5
Total with taxes and fees
Badgers Sett
Exterior detail

2. The Old Chapel Retreat

The Old Chapel Retreat
Staindrop, Barnard Castle
10.0 out of 10, Exceptional, (15 reviews)
"A fabulous house for a family get together. The house had everything we needed even with Covid restrictions. The welcome pack was a lovely touch. The perfect base with lots to do in the area. Review independently collected and verified by Reevoo"
United States
Emma
$1,052 nightly
The price is $1,052
Sep 30 - Oct 1
Total with taxes and fees
The Old Chapel Retreat
Terrace/patio

3. CAESARS LODGE, pet friendly, luxury holiday cottage in Heighington

CAESARS LODGE, pet friendly, luxury holiday cottage in Heighington
2.0 star property
Darlington
$2,180 nightly
The price is $2,180
Aug 31 - Sep 1
Total with taxes and fees
CAESARS LODGE, pet friendly, luxury holiday cottage in Heighington
Interior

4. 2 bedroom accommodation in Barnard Castle

2 bedroom accommodation in Barnard Castle
Barnard Castle
10.0 out of 10, Exceptional, (5 reviews)
"Spent a lovely week at Ashlea Country Cottage, Ann, the owner was so nice and helpful, made us feel right at home from the moment we arrived. This is a lovely cosy cottage set in beautiful peaceful surroundings. We even got real thick snow which was an added bonus, great to watch surrounding wildlife and had visits from sheep. The wood burner was a real hit, made the cottage feel homely and warm, great place to explore from and the fresh warm bread on arrival was an absolute bonus. We will be...
United States
Stephen Bamber
$356 nightly
The price is $356
Sep 29 - Sep 30
Total with taxes and fees
2 bedroom accommodation in Barnard Castle
Front of property

5. Stable Yard Rooms

Stable Yard Rooms
3.0 star property
Richmond
7.4 out of 10, Good, (3 reviews)
"The property is excellent for a one night stay. Only negative is there is nowhere to sit and eat your breakfast."
United Kingdom
Nadine
$86 nightly
The price is $103
Sep 13 - Sep 14
Total with taxes and fees
Stable Yard Rooms
Room

6. The Etherley Holiday Cottage

The Etherley Holiday Cottage
Bishop Auckland
10.0 out of 10, Exceptional, (8 reviews)
"Great stay lovely house thank you."
United Kingdom
Richard F.
$179 nightly
The price is $179
Aug 31 - Sep 1
Total with taxes and fees
The Etherley Holiday Cottage
House

7. Two Bedroom Family Apartment Near Town Centre Chic Stay

Two Bedroom Family Apartment Near Town Centre Chic Stay
2.0 star property
Darlington
$304 nightly
The price is $364
Sep 2 - Sep 3
Total with taxes and fees
Two Bedroom Family Apartment Near Town Centre Chic Stay
Terrace/patio

8. Superking beds, spacious and comfortable ground floor apartment near town centre

Superking beds, spacious and comfortable ground floor apartment near town centre
Bishop Auckland
9.6 out of 10, Exceptional, (19 reviews)
"Lovely, spacious property. Spotlessly clean. All mod cons present with extras, Lovely coffee, bread in the freezer. Great location for town centre and walking distance for Kynren. Very comfortable beds. Would definitely recommend to anyone."
United Kingdom
Pauline
$130 nightly
The price is $130
Sep 1 - Sep 2
Total with taxes and fees
Superking beds, spacious and comfortable ground floor apartment near town centre
Living area

9. Superking beds, spacious and comfortable first floor apartment near town centre

Superking beds, spacious and comfortable first floor apartment near town centre
Bishop Auckland
9.0 out of 10, Wonderful, (21 reviews)
"We stayed for daughter's graduation in Durham for two nights. Roons a great size loved the quirkiness if the property. Had every yuou could need. Wish this property was in Durham only easier for travelling"
United Kingdom
Shelley
$150 nightly
The price is $150
Sep 3 - Sep 4
Total with taxes and fees
Superking beds, spacious and comfortable first floor apartment near town centre
Outdoor dining

10. A cosy hillside hideaway in the heart of the Yorkshire Dales

A cosy hillside hideaway in the heart of the Yorkshire Dales
Richmond
10.0 out of 10, Exceptional, (4 reviews)
"The condition of the cottage was outstanding, excellent in fact and the location was fantastic!"
United Kingdom
GAVIN T.
$817 nightly
The price is $817
Sep 20 - Sep 21
Total with taxes and fees
A cosy hillside hideaway in the heart of the Yorkshire Dales
Cottage | Property grounds

11. Sunny Cottage

Sunny Cottage
3.5 star property
Darlington
$484 nightly
The price is $581
Sep 3 - Sep 4
Total with taxes and fees
Sunny Cottage
Living area

12. Pets - Parking - Patio - Wifi - Sleeps 4

Pets - Parking - Patio - Wifi - Sleeps 4
3.0 star property
Bishop Auckland
$59 nightly
The price is $71
Sep 30 - Oct 1
Total with taxes and fees
Pets - Parking - Patio - Wifi - Sleeps 4
Dining

13. 5 bedroom accommodation in Hudswell, near Richmond

5 bedroom accommodation in Hudswell, near Richmond
Hudswell, near Richmond
9.2 out of 10, Wonderful, (15 reviews)
"Overall our stay was fantastic, comfortable and useable property . Great base for exploring the local area ."
United States
Mark Hawkins
$573 nightly
The price is $573
Sep 28 - Sep 29
Total with taxes and fees
5 bedroom accommodation in Hudswell, near Richmond
Outdoor dining

14. Cosy, Dog Friendly Cottage w/ Free WiFi, Woodburner, a good size garden and a short walk to two pubs

Cosy, Dog Friendly Cottage w/ Free WiFi, Woodburner, a good size garden and a short walk to two pubs
Richmond
9.4 out of 10, Exceptional, (9 reviews)
"great location"
United Kingdom
Paul P.
$478 nightly
The price is $478
Sep 1 - Sep 2
Total with taxes and fees
Cosy, Dog Friendly Cottage w/ Free WiFi, Woodburner, a good size garden and a short walk to two pubs
Exterior

15. High-quality bolthole and cosy sanctuary for 2 people in a picturesque village location with WiFi.

High-quality bolthole and cosy sanctuary for 2 people in a picturesque village location with WiFi.
Richmond
9.8 out of 10, Exceptional, (7 reviews)
"Cottage in a beautiful area, cottage nestled in the heart of an unspoilt village. Cosy, well equipped, private and a perfect little bolthole."
United Kingdom
Victoria
$540 nightly
The price is $540
Aug 31 - Sep 1
Total with taxes and fees
High-quality bolthole and cosy sanctuary for 2 people in a picturesque village location with WiFi.
Private kitchen

16. A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.

A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.
Richmond
9.8 out of 10, Exceptional, (15 reviews)
"We loved our stay in this spacious cottage in a picturesque setting. There is all the appliances you need, including a washer/dryer. The location is excellent for the many hikes in the area."
United States
Diana v.
$510 nightly
The price is $510
Sep 4 - Sep 5
Total with taxes and fees
A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.
Living area

17. 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.
$650 nightly
The price is $650
Sep 1 - Sep 2
Total with taxes and fees
A fantastic, 2 bed cottage, sleeping 4 people and 1 furry friend w/open fire, WiFi & central heating
Interior

18. 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
9.6 out of 10, Exceptional, (4 reviews)
"lovely property in a good location."
United States
Tim B.
$678 nightly
The price is $678
Sep 1 - Sep 2
Total with taxes and fees
A cosy stone cottage with stunning views, village charm, and adventure at your doorstep
Terrace/patio

19. Holiday home for 4 people, breath taking scenery, bike storage, WiFi & only a short walk to the pub.

Holiday home for 4 people, breath taking scenery, bike storage, WiFi & only a short walk to the pub.
Richmond
9.4 out of 10, Exceptional, (10 reviews)
"Great location with great walks. Cottage was outstandingly clean and comfortable, the welcome pack was a lovely touch. Would definitely stop at this cottage again."
United Kingdom
josephine G.
$897 nightly
The price is $897
Sep 2 - Sep 3
Total with taxes and fees
Holiday home for 4 people, breath taking scenery, bike storage, WiFi & only a short walk to the pub.
Living area

20. An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, WiFi.

An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, WiFi.
Richmond
10.0 out of 10, Exceptional, (11 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.
$600 nightly
The price is $600
Sep 28 - Sep 29
Total with taxes and fees
An exceptional holiday home for 6 people & 2 dogs with multi-fuel stove, 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 Winston Hotel Reviews

Crathorne Hall Hotel

Crathorne Hall Hotel

10/10 Excellent
"Breakfast was excellent and lots of variety"
david 3-night trip
Posted 2 days ago
Crathorne Hall Hotel

Find out more about Winston

Everything you need to know about Winston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $70 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winston rentals

At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winston?

Yes, we have vacation rentals close to well known local attractions in Winston, or you can select a secluded option if you're looking for relaxation.

What's the top vacation rental in Winston?

🌿 Bee and Bath Hot Tub Hideaway Durham ~Steam Spa~Roll Top Bath~Pets~Diggerland: Visitors like this Winston vacation home rental. It offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 Whitworth Hall Country Park. In the larger area, you’ll find Raby Castle and Barnard Castle.

What’s a vacation rental in Winston like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Winston. Vacation rentals feature extras like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.