Winston Vacations from $952

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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.
Woodlands Guest House Windermere

Woodlands Guest House Windermere

4 out of 5
Price was $1,028, price is now $952 per person
$952
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Durham (MME)
9.2/10 Wonderful! (612 reviews)
Sound proofing. The creaks and chatter from above and neighbouring rooms are very loud.

Reviewed on Jan 26, 2026

The Brown Horse Inn

The Brown Horse Inn

3.5 out of 5
Price was $1,092, price is now $1,021 per person
$1,021
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Durham (MME)
9.6/10 Exceptional! (134 reviews)
Very friendly, and a good atmosphere, food excellent.

Reviewed on Oct 24, 2025

Cedar Manor

Cedar Manor

5 out of 5
Price was $1,274, price is now $1,194 per person
$1,194
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Durham (MME)
9.8/10 Exceptional! (103 reviews)
Room was lovely, clean and thoughtful touches. The public areas bar dining room lovely comfortable seating. Highly recommend as location to the town is ideal easy walk.

Reviewed on Dec 7, 2025

Windermere Manor Hotel

Windermere Manor Hotel

3.5 out of 5
Price was $1,114, price is now $1,050 per person
$1,050
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Durham (MME)
8/10 Very Good! (661 reviews)
Was very clean. Staff was lovely just needed more options for breakfast tomato’s and mushrooms

Reviewed on Jan 18, 2026

Beaumont House with FREE off-site Health Club - Adults Only

Beaumont House with FREE off-site Health Club - Adults Only

5 out of 5
Price was $1,190, price is now $1,122 per person
$1,122
per person
Apr 23 - Apr 26
found 2 hours ago
Roundtrip flight included
New York (NYC) to Durham (MME)
9.6/10 Exceptional! (129 reviews)
Very nice relaxed accomodations. Close to the train station and the main street. Very welcoming and kind.

Reviewed on Sep 27, 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 Raby with Keverstone, 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 top-notch restaurants in this quaint area.

The Darlington Arena

Winston Hotel Deals

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
$80 nightly
The price is $96 total per night from Feb 9 to Feb 10
$96 total
Feb 9 - Feb 10
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Room was comfortable, staff courteous and good parking

Reviewed on Jan 23, 2026

Delta Hotels Durham Royal County
Radisson BLU Hotel Durham

Radisson BLU Hotel Durham

4 out of 5
Frankland Lane Durham England
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $127 total per night from Feb 8 to Feb 9
$127 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Excellent location

Reviewed on Jan 25, 2026

Radisson BLU Hotel Durham
Redworth Hall Hotel

Redworth Hall Hotel

4 out of 5
Redworth Newton Aycliffe England
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,008 reviews)
Wide choice for breakfast, well kept room, the staff were friendly and very professional/polite

Reviewed on Jan 22, 2026

Get rates
Redworth Hall Hotel
See all 2,013 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.

Find the Best Winston Vacation Packages

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 $952 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.