Winston Vacations from $1,416

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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.
Denecrest Guest House

Denecrest Guest House

2 out of 5
Price was $1,526, price is now $1,416 per person
$1,416
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to Durham (MME)
9.4/10 Exceptional! (6 reviews)
Great location for Windermere town centre

Reviewed on Jul 19, 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 $1,806, price is now $1,655 per person
$1,655
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to Durham (MME)
9.6/10 Exceptional! (134 reviews)
Nice hotel with ample parking and fair sized rooms. I've stayed in many hotels in the area and this is the first time where B&B does not include an English breakfast. Apparently this has to be ordered the day before and payed as a surcharge??? Very disappointing. Why not just include it in the price?

Reviewed on Jul 25, 2026

Low Wood Bay Resort & Spa

Low Wood Bay Resort & Spa

4 out of 5
Price was $2,096, price is now $1,925 per person
$1,925
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to Durham (MME)
8.6/10 Excellent! (743 reviews)

Hawksmoor Guest House

Hawksmoor Guest House

4 out of 5
Price was $1,658, price is now $1,525 per person
$1,525
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to Durham (MME)
9.8/10 Exceptional! (276 reviews)
Every thing is good. I really could not complain anything. Highly recommend.

Reviewed on Jul 27, 2026

Howbeck Guest House

Howbeck Guest House

5 out of 5
Price was $1,625, price is now $1,540 per person
$1,540
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Port of Spain (POS) to Durham (MME)
9.2/10 Wonderful! (147 reviews)

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Winston Hotel Deals

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 Sep 6 to Sep 7
$102 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (1,008 reviews)
"The staff were fantastic, really nice. The room was massive, but missed out on 5-star as the shower was pathetic; there was a better shower in the pool. Food was a good selection, and the beer on tap was fantastic. Overall, I had a great break. It would have been excellent if the shower in the room ..."

Reviewed on Aug 5, 2026

Redworth Hall Hotel
The Kings Head Hotel, Richmond, North Yorkshire

The Kings Head Hotel, Richmond, North Yorkshire

4 out of 5
Market Place Richmond England
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $133 total per night from Aug 9 to Aug 10
$133 total
Aug 9 - Aug 10
Total with taxes and fees
The Kings Head Hotel, Richmond, North Yorkshire
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
$96 nightly
The price is $115 total per night from Aug 31 to Sep 1
$115 total
Aug 31 - Sep 1
Total with taxes and fees
Delta Hotels Durham Royal County
See all 2,216 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 $1,416 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.