Winston Vacations from $743

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Your Winston Vacation

The exciting city of Winston is calling. Discover its hot spots and hidden treasures with a Winston vacation package that's customized to you. You'll want to take in the sights during your trip to Winston. Make time for famous attractions like Barnard Castle, Raby Castle and Bowes Museum. Expedia will help you escape the everyday. Tailor your vacation to Winston to suit your style of travel, whatever that may look like.

The Latest Winston vacation packages

Price found within the past 48 hours. Click for updated prices.
Rum Doodle B&B

Rum Doodle B&B

4 out of 5
Price was $785, price is now $743 per person
$743
per person
Nov 19 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Durham (MME)
9.6/10 Exceptional! (178 reviews)
This quaint property was within walking distance of Windermere. There is also a bus you can catch just around the corner. Our room was clean and well appointed but only had a bath which my husband struggled with. The breakfast was adequate and served by a bright and friendly lady. Check in could have been better by offering some additional information regarding the bus service to town and maybe some suggestions of things to do in the area or good restaurants to eat at. Overall a great stay, thank you.

Reviewed on Oct 14, 2025

Windermere Manor Hotel

Windermere Manor Hotel

3.5 out of 5
Price was $990, price is now $841 per person
$841
per person
Nov 19 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Durham (MME)
8/10 Very Good! (658 reviews)
Lovely hotel with kind staff. Only bad thing was rooms were far to hot and hard to sleep.

Reviewed on Oct 12, 2025

Shap Wells Hotel

Shap Wells Hotel

3 out of 5
Price was $1,035, price is now $883 per person
$883
per person
Nov 19 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Durham (MME)
8.2/10 Very Good! (523 reviews)
Lovely quaint hotel.

Reviewed on Oct 9, 2025

Denecrest Guest House

Denecrest Guest House

2 out of 5
Price was $888, price is now $827 per person
$827
per person
Nov 19 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Durham (MME)
10/10 Exceptional! (1 review)
The Three Shires Inn

The Three Shires Inn

4 out of 5
Price was $1,094, price is now $1,062 per person
$1,062
per person
Nov 19 - Nov 25
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Durham (MME)
9.6/10 Exceptional! (82 reviews)
Really great value for money, lovely surroundings and beautiful hotel.

Reviewed on Aug 24, 2025

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Discover the most popular places to visit in Winston

Reflection on the water

Raby Castle

Raby Castle is just one of the places to see in Darlington, so why not enjoy the other things to explore during your travels? Check out the spas and lively bars in this relaxing area.

Raby Castle

Rockliffe Hotel Spa

You can take time to visit Rockliffe Hotel Spa during your travels to Hurworth-on-Tees. Check out the spas and lively bars in this relaxing area.

Rockliffe Hotel Spa

The Darlington Arena

Catch an event at The Darlington Arena during your trip to Darlington. Check out the spas and lively bars in this relaxing area.

The Darlington Arena

Winston Hotel Deals

Radisson BLU Hotel Durham

Radisson BLU Hotel Durham

4 out of 5
Frankland Lane, Durham, England
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $132 total per night from Oct 26 to Oct 27
$132 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Nice spa area and the area around the hotel was nice. Train station is relatively close but would advise a taxi or uber due to elevation difference"

Reviewed on Oct 12, 2025

Radisson BLU Hotel Durham
Delta Hotels Durham Royal County

Delta Hotels Durham Royal County

4 out of 5
Old Elvet, Durham, England
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $113 total per night from Oct 27 to Oct 28
$113 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"Have to pay for the car park as it’s privately owned which I find disgraceful, hotels should provide free parking not sell their car park, put me off"

Reviewed on Oct 15, 2025

Delta Hotels Durham Royal County
Redworth Hall Hotel

Redworth Hall Hotel

4 out of 5
Redworth, Newton Aycliffe, England
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $102 total per night from Oct 23 to Oct 24
$102 total
Oct 23 - Oct 24
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Lovely, relaxing 2 day break at Redworth. Friendly staff, excellent leisure facilities and well-equipped room."

Reviewed on Oct 18, 2025

Redworth Hall Hotel
See all 1,806 properties in Winston
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.

Winston Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Teesside Intl. Airport (MME)
Top Sights
Raby Castle, Darlington Civic Theatre and Raby Castle

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Frequently asked questions

How much does a Winston vacation package cost?
Offering excellent value package deals from $743 on Expedia, you'll be surprised at how little a vacation to Winston costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Winston?
You can usually find lower rates and greater availability in December, January and February. Browse our cheap Winston vacation packages and you could land some great off-season discounts.
How many days is enough for Winston?
With a well-organized itinerary, you can easily visit the main Winston attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your Winston vacation for longer.
How to find the best Winston package deals?
Begin your search for a Winston package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winston package deal right away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winston adventure off to a flying start.
Is it cheaper to book a Winston vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a customized Winston vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Winston?
If you're considering a spur-of-the-moment Winston getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Winston vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Winston trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.