Winston Vacation Rentals from CA $93: Short-Term Rentals for 2026

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Our top choices for Winston vacation rentals

A stone gate leading to a courtyard with a bench and a small tree.

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

Bishop Auckland

Gregory

CA $181 total

includes taxes & fees

Oct 12 - Oct 13

A two-story building with multiple windows, some with shutters, and a well-lit entrance.

2. Stable Yard Rooms

Richmond

Nadine

CA $224 total

includes taxes & fees

Oct 12 - Oct 13

A stone building with a green door, a window with lace curtains, and potted plants outside.

3. Wayside Cottage

Darlington

CA $525 total

includes taxes & fees

Oct 15 - Oct 16

A bedroom with a bed, a dresser, and three framed botanical prints on the wall.

4. Central Bishopauckland - House - Stay5 - Pooltable

Bishop Auckland

CA $477 total

includes taxes & fees

Oct 13 - Oct 14

A cozy living room with a fireplace, a television, and comfortable seating.

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

Bishop Auckland

Shelley

CA $257 total

includes taxes & fees

Oct 12 - Oct 13

A compact living space with a kitchenette, grey sofa, and a door leading to another room.

6. 11 Larchfield House

Darlington

CA $210 total

includes taxes & fees

Oct 12 - Oct 13

A hallway with carpeted stairs leading to a room, a white door, and a small table with a plant.

7. 17 Larchfield House

Darlington

CA $307 total

includes taxes & fees

Oct 12 - Oct 13

A green door with a metal knocker, flanked by two potted plants with pink flowers, and a mailbox on the left.

8. The Old Chapel Retreat

Staindrop, Barnard Castle

Kirsty Leslie

CA $1,334 total

includes taxes & fees

Oct 15 - Oct 16

A stone building with a wooden door and windows. There are potted plants and flowers on the steps.

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

Middleton-in-Teesdale

Julie N.

CA $300 total

includes taxes & fees

Oct 12 - Oct 13

A neatly made bed with white linens and a wooden headboard, a bedside table with a clock, and a radiator on the wall.

10. The Old Colliery Stables

Durham

Terry

CA $123 total

includes taxes & fees

Oct 12 - Oct 13

A hotel room with two beds, teal bedding, white pillows with circular patterns, and a wall art of blue flowers.

11. 2 bedroom accommodation in Shildon, near Bishop Auckland

Shildon, near Bishop Auckland

Anna M.

CA $496 total

includes taxes & fees

Oct 14 - Oct 15

A stone cottage with a light-colored door, a window with a curtain, and a sign reading "Willow Cottage."

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

Middleton-in-Teesdale

Claire B.

CA $322 total

includes taxes & fees

Oct 12 - Oct 13

A cozy wooden cabin bedroom with a bed, a small kitchenette, and a view of the forest.

13. The Leveret

Richmond

Poppy

CA $726 total

includes taxes & fees

Oct 18 - Oct 19

A living room with a sofa, a coffee table, a fireplace, and a chandelier.

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

Bishop Auckland

Rajalingham

CA $93 total

includes taxes & fees

Oct 26 - Oct 27

A dining area with a wooden table and chairs, a vase, and a cabinet with glass doors.

15. 5 bedroom accommodation in Hudswell, near Richmond

Hudswell, near Richmond

Mark Hawkins

CA $798 total

includes taxes & fees

Oct 14 - Oct 15

A wooden shelf with decorative items and books.

16. The Den - Small but cosy apartment in the Dales.

Leyburn

JOANNE

CA $157 total

includes taxes & fees

Oct 13 - Oct 14

17. Modern Self-catering Apartment - The Holt

Leyburn

Janet

CA $179 total

includes taxes & fees

Nov 2 - Nov 3

A stone cottage with a black metal fence, a sign reading "Ivy Cottage," and a small garden area.

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

Richmond

Victoria

CA $590 total

includes taxes & fees

Nov 9 - Nov 10

A neatly made bed with a striped bedspread, a bedside table with a lamp, and two framed botanical prints on the wall.

19. The Drey Apartment - self-catered Dales luxury

Leyburn

Kevin

CA $189 total

includes taxes & fees

Oct 15 - Oct 16

A modern living room with a grey sofa, white coffee table, and a vase of yellow flowers.

20. White House Cottages

Durham

Ashley

CA $179 total

includes taxes & fees

Oct 15 - Oct 16

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Top Winston Hotel Reviews

The Kings Head Hotel, Richmond, North Yorkshire

10/10 Excellent

"We stayed one night on way north. Nice room. Nice evening meal. Paid £10 to park overnight at hotel. Did not want to pay £32 for breakfast for two (went to The Station). Very central. Would recommend."

Redworth Hall Hotel

10/10 Excellent

"An extremely warm welcome at reception was followed by an offer to upgrade our room to accommodate for a mobility issue. Throughout our stay all staff were extremely friendly and helpful. Breakfast was good but lacked a couple of items that I expect to be on the menu. Overall, I would highly recommend booking this Hotel."

Hotel Indigo Durham by IHG

8/10 Good

"The staff is absolutely 5 star! They go above and beyond and truly make you feel like a guest … they’re so helpful and kind ! My only con about this property is the lack of a traditional lobby with seating area etc, the cafe downstairs is dark and gloomy although the scones are delicious and the staff is super kind as well !"

Honest Lawyer Hotel

8/10 Good

"Good and reasonably priced Hotel with Great Food The check in was a quick and easy process. The room was a good size with a decent sized table to use my laptop on, good amount of power points, and with the decent speed free internet made it a very useful stop over. The shower and bathroom were good, but let down a bit by tatty worn painting work, along with the extractor fan not being hoovered out and quite dusty. The window opening and fascia above were tatty and quite dirty. Unfortunately the bed was squeaky when you moved, and wasn’t too comfortable. The food in the bar was very good, good portions, tasty and reasonably priced. The staff in the pub were friendly and efficient, and the service was quick, including bringing the food out to us. The room was quiet and had good views of woodland at the back, and was not affected by any light from the front of the Hotel car park. The parking right outside the rooms were great, peace of mind the car was visible and good lighting in the car park, making it a reassuring feeling parking the car. At the price point it was a reasonably priced stop over."

Find out more about Winston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

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Check prices for these dates

Our top choices for Winston vacation rentals

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

2. Stable Yard Rooms

3. Wayside Cottage

4. Central Bishopauckland - House - Stay5 - Pooltable

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

6. 11 Larchfield House

7. 17 Larchfield House

8. The Old Chapel Retreat

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

10. The Old Colliery Stables

11. 2 bedroom accommodation in Shildon, near Bishop Auckland

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

13. The Leveret

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

15. 5 bedroom accommodation in Hudswell, near Richmond

16. The Den - Small but cosy apartment in the Dales.

17. Modern Self-catering Apartment - The Holt

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

19. The Drey Apartment - self-catered Dales luxury

20. White House Cottages

Find vacation rentals that suit your style

Top Winston Hotel Reviews

The Kings Head Hotel, Richmond, North Yorkshire

Redworth Hall Hotel

Hotel Indigo Durham by IHG

Honest Lawyer Hotel

Delta Hotels Durham Royal County

Hampton by Hilton Stockton on Tees

Blackwell Grange Hotel

Holiday Inn Darlington - A1 Scotch Corner by IHG

The Old Mill Rooms

Find out more about Winston

Frequently asked questions

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