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Winston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winston vacation rentals

A kitchen with white cabinets, a wooden table, and a vase of flowers.

1. The Old Chapel Retreat

The Old Chapel Retreat
Staindrop, Barnard Castle
10.0 out of 10, Exceptional, (15 reviews)
"A brilliant holiday home that had everything we needed and more. Everything was clean and comfortable. The children loved the games room with pool tables. The welcome pack was a lovely touch! It was a great place to explore the area."
United States
Kirsty Leslie
$1,106 nightly
The price is $1,106
Nov 8 - Nov 9
Total with taxes and fees
The Old Chapel Retreat
A two-story building with multiple windows, some with shutters, and a well-lit entrance.

2. 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
$124 nightly
The price is $149
Dec 6 - Dec 7
Total with taxes and fees
Stable Yard Rooms
A cozy wooden cabin bedroom with a bed, a small kitchenette, and a view of the forest.

3. The Leveret

The Leveret
2.0 star property
Richmond
10.0 out of 10, Exceptional, (4 reviews)
"What a lovely little spot, we really enjoyed our time here, it had everything we needed and our dog absolutely loved it! Very clean, had all the essentials and had a pub close enough to wander down to. "
United Kingdom
Poppy
$432 nightly
The price is $519
Nov 17 - Nov 18
Total with taxes and fees
The Leveret
A conservatory with wicker furniture, a laptop, and a vase of flowers.

4. 2 bedroom accommodation in Barnard Castle

2 bedroom accommodation in Barnard Castle
Barnard Castle
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful cottage in a lovely setting. The owners were very hospitable & the cottage was well equipped & very clean. Overlooking countryside with lots of wildlife around."
United States
Pete & Sue
$333 nightly
The price is $333
Nov 14 - Nov 15
Total with taxes and fees
2 bedroom accommodation in Barnard Castle
A stone gate leading to a courtyard with a bench and a small tree.

5. 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, (23 reviews)
"Lovely apartment, we plan to be regular visitors if possible."
United Kingdom
Michael
$154 nightly
The price is $154
Nov 9 - Nov 10
Total with taxes and fees
Superking beds, spacious and comfortable ground floor apartment near town centre
A living room with a sofa, a coffee table, a fireplace, and a chandelier.

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

Pets - Parking - Patio - Wifi - Sleeps 4
3.0 star property
Bishop Auckland
10.0 out of 10, Exceptional, (2 reviews)
"Great communication from owner, easy lockbox access when we turned up in the early hours. House was large with comfortable space for the four us. Nice and clean with nice shower after the show we had just played. Will definitely return"
United Kingdom
Neil
$49 nightly
The price is $59
Nov 15 - Nov 16
Total with taxes and fees
Pets - Parking - Patio - Wifi - Sleeps 4
A cozy living room with a fireplace, a television, and comfortable seating.

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

Superking beds, spacious and comfortable first floor apartment near town centre
Bishop Auckland
9.2 out of 10, Wonderful, (25 reviews)
"Great location for what we wanted. Very clean with everything we needed."
United Kingdom
Dennis
$177 nightly
The price is $177
Nov 8 - Nov 9
Total with taxes and fees
Superking beds, spacious and comfortable first floor apartment near town centre
A modern living room with a grey sofa, white coffee table, and a vase of yellow flowers.

8. White House Cottages

White House Cottages
3.5 star property
Durham
9.6 out of 10, Exceptional, (44 reviews)
"Fabulous location & accommodation, thoroughly enjoyed !"
United Kingdom
Ashley
$107 nightly
The price is $128
Nov 6 - Nov 7
Total with taxes and fees
White House Cottages
A hotel room with two beds, teal bedding, white pillows with circular patterns, and a wall art of blue flowers.

9. 2 bedroom accommodation in Shildon, near Bishop Auckland

2 bedroom accommodation in Shildon, near Bishop Auckland
Shildon, near Bishop Auckland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay, very well equipped and comfy beds. Very clean and well laid out, great location."
United Kingdom
Anna M.
$354 nightly
The price is $354
Nov 19 - Nov 20
Total with taxes and fees
2 bedroom accommodation in Shildon, near Bishop Auckland
A dining area with a wooden table and chairs, a vase, and a cabinet with glass doors.

10. 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
$476 nightly
The price is $476
Nov 30 - Dec 1
Total with taxes and fees
5 bedroom accommodation in Hudswell, near Richmond
A quaint village street with stone buildings, a church, and a car park.

11. 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, (12 reviews)
"Great little place in a prime location in a fantastic location. The layout is quirky but part of the charm and a wonderful view from the sitting / dining / kitchen area"
United Kingdom
Ian
$356 nightly
The price is $356
Nov 9 - Nov 10
Total with taxes and fees
Beautiful, 2 bedroom, first floor apartment, at the heart of a busting Dales Village.
A stone building with a wooden door and windows. There are potted plants and flowers on the steps.

12. Cosy 2 bed-room cottage near High Force Waterfall

Cosy 2 bed-room cottage near High Force Waterfall
Middleton-in-Teesdale
10.0 out of 10, Exceptional, (3 reviews)
"Great communication really enjoyed our stay would reccomend"
United States
Julie N.
$213 nightly
The price is $213
Nov 19 - Nov 20
Total with taxes and fees
Cosy 2 bed-room cottage near High Force Waterfall
A kitchen with a wooden island, stainless steel sink, and pendant lights.

13. The Cartshed, Sedbury Park Farm

The Cartshed, Sedbury Park Farm
3.0 star property
Richmond
10.0 out of 10, Exceptional, (1 review)
$615 nightly
The price is $738
Nov 9 - Nov 10
Total with taxes and fees
The Cartshed, Sedbury Park Farm
A stone cottage with a light-colored door, a window with a curtain, and a sign reading "Willow Cottage."

14. Willow Cottage, cosy & quirky in Middleton in Teesdale

Willow Cottage, cosy & quirky in Middleton in Teesdale
Middleton-in-Teesdale
8.8 out of 10, Excellent, (3 reviews)
"Such a cute and cosy cottage, had everything we needed and was very well situated. thank you."
United Kingdom
Claire B.
$205 nightly
The price is $220
Nov 6 - Nov 7
Total with taxes and fees
Willow Cottage, cosy & quirky in Middleton in Teesdale
A cozy living room with a fireplace, a television, and a comfortable seating area.

15. 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.
$486 nightly
The price is $486
Nov 23 - Nov 24
Total with taxes and fees
A fantastic, 2 bed cottage, sleeping 4 people and 1 furry friend w/open fire, WiFi & central heating
A stone building with a sloped roof, a narrow stream running alongside, and a road in the foreground.

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, (16 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.
$444 nightly
The price is $444
Nov 21 - Nov 22
Total with taxes and fees
A superb holiday home within the Yorkshire Dales, w/ Wifi, wood burner & stones throw from pub.
A stone cottage with a green door, a bench outside, and a view of the countryside.

17. 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)
"Very nice cottage in perfect location"
United Kingdom
Ian H.
$567 nightly
The price is $567
Nov 6 - Nov 7
Total with taxes and fees
Low Cottage, a dog friendly holiday home for up to four people in the pretty village of Reeth.
A compact kitchen with a microwave, stove, and white tiled backsplash. A wicker sofa is positioned near a doorway leading to a bedroom.

18. Durham City Cottages

Durham City Cottages
2.0 star property
Durham
8.0 out of 10, Very good, (411 reviews)
"Bathroom smells mouldy, could have done with a small window opener for airflow.kitchen has everything you need.parking perfect outside accommodation Overall a good place to stay"
United Kingdom
Steven
$96 nightly
The price is $115
Nov 11 - Nov 12
Total with taxes and fees
Durham City Cottages
A brick building with a sign for 'The Duke Of Wellington COURTYARD ROOMS.' There are picnic tables with umbrellas, a gravel courtyard, and a staircase leading to the entrance.

19. Welbury Studio, Sleeps 2, Pet Friendly & Parking

Welbury Studio, Sleeps 2, Pet Friendly & Parking
3.0 star property
Northallerton
9.6 out of 10, Exceptional, (5 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
$67 nightly
The price is $80
Nov 13 - Nov 14
Total with taxes and fees
Welbury Studio, Sleeps 2, Pet Friendly & Parking
A modern building with a combination of dark siding and wooden accents, featuring multiple windows and a door with a small set of stairs leading up to it.

20. 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
$165 nightly
The price is $198
Nov 11 - Nov 12
Total with taxes and fees
Old Mill Tiny Homes
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

Hall Garth Hotel Darlington, Sure Hotel Collection by BW

Hall Garth Hotel Darlington, Sure Hotel Collection by BW

8/10 Good
"The staff at the hotel are very friendly and helpful, nice warm welcome. This hotel is lovely, unfortunately the owners don’t appear to want to spend any money maintaining the building. The rooms are clean but cracked floor tiles in the bathroom, ceiling damaged and not repaired properly or repainted. The beds are comfortable and linen is spotless."
Emma 1-night trip
Posted 5 hours ago
Hall Garth Hotel Darlington, Sure Hotel Collection by BW

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 $59 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?

Grand Country Estate 3 Hot Tubs Sleeps 16 near Durham City & Bishop Auckland: You might want to consider this vacation home rental near Winston, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Raby Castle and Bowes Museum.

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.