Winston Vacation Packages 2026 from $1,445

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.

Hawksmoor Guest House

$1,445

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Durham (MME)

9.8/10 Exceptional! (269 reviews)

clean room but small. excellent breakfast, easy walk to restsurants

Reviewed on Mar 1, 2026

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

$1,660

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Durham (MME)

9.6/10 Exceptional! (130 reviews)

Lovely & clean & in an ideal location. Breakfast was very nice & the hosts were very good.

Reviewed on May 4, 2026

Macdonald Old England Hotel & Spa

$1,630

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Durham (MME)

8.2/10 Very Good! (1,003 reviews)

Hotel location was A+++. Staff were fantastic. Would highly recommend!

Reviewed on May 29, 2026

Fair Rigg by Cradel Haus

$1,737

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Durham (MME)

9/10 Wonderful! (17 reviews)

The place is very beautiful, but the checkout time is very early.

Reviewed on Jun 1, 2026

Another Place The Lake

$2,345

per person

Jul 19 - Jul 23

found 1 day ago

Roundtrip non-stop flight included

Chicago (ORD) to Durham (MME)

10/10 Exceptional! (3 reviews)

Beautiful grounds and spacious room

Reviewed on May 22, 2026

Don't see what you're looking for?

See all available trips from Columbus to Winston

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Discover the most popular places to visit in Winston

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.

Rockliffe Hotel Spa

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

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.

Winston Hotel Deals

Delta Hotels Durham Royal County

Old Elvet Durham England

Fully refundableReserve now, pay when you stay

$96 nightly

$115 total

Jun 7 - Jun 8

Total with taxes and fees

9/10 Wonderful! (1,003 reviews)

"Happy with my stay. Parking is on site, but costs extra. The staff will help you if the car park is full."

Reviewed on Jun 3, 2026

Radisson BLU Hotel Durham

Frankland Lane Durham England

Fully refundableReserve now, pay when you stay

$110 nightly

$132 total

Jun 7 - Jun 8

Total with taxes and fees

8.8/10 Excellent! (1,008 reviews)

"Hotel was of excellent standard, room was very comfortable, breakfast was good and hotel very well presented. Only minor issue was rolling back in the hotel around 10pm and hoping to grab something to eat, we didn't expect the resturant to be open but hoped we could have something light or even room ..."

Reviewed on Jun 1, 2026

Redworth Hall Hotel

Redworth Newton Aycliffe England

Fully refundableReserve now, pay when you stay

$90 nightly

$108 total

Jun 7 - Jun 8

Total with taxes and fees

8.4/10 Very Good! (1,004 reviews)

"The staff at this lovely hotel were lovely and friendly. The room was spacious, Clean and modern and loved it. The swimming pool and amenities were fantastic as well. We ate at the bar which was tasty and enjoyed the bar area for some beverages. We also visited Beamish which was local to this ..."

Reviewed on Jun 1, 2026

See all 2,120 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 $1,445 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.

Winston Vacations from $1,445

Book a Hotel + Flight or Car together to unlock savings

Room 1

Your Winston Vacation

The Latest Winston vacation packages

Hawksmoor Guest House

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

Macdonald Old England Hotel & Spa

Fair Rigg by Cradel Haus

Another Place The Lake

Discover the most popular places to visit in Winston

Raby Castle

Rockliffe Hotel Spa

The Darlington Arena

Winston Hotel Deals

Delta Hotels Durham Royal County

Radisson BLU Hotel Durham

Redworth Hall Hotel

Find the Best Winston Vacation Packages

Winston Essential Information

More vacations you might like

Frequently asked questions