Old Town Winchester Holidays from £640

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Your Old Town Winchester Holiday

Book a customized holiday package to Old Town Winchester and experience the charms of this neighbourhood from dawn to dusk. From its cafes and history to its unique personality and vibe, there are tons of fabulous reasons to visit Old Town Winchester. Can't wait to get out and see the sights during your trip to Old Town Winchester? Pencil in a visit to nearby attractions such as Shenandoah University, Rock Harbour Golf Course and Museum of the Shenandoah Valley. Stop daydreaming and start doing. When you're ready to lock in your holiday to Old Town Winchester, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
6 Oct - 11 Oct
found 24 hours ago
Return flight included
London (LHR) to Washington (WAS)
8/10 Very Good! (968 reviews)
Hotel was not so good front of hotel we have to pay parking most of hotels are packed free bcz I’m staying this hotel gives business should free parking however we went early lady receptionist she help us early check in was easy

Reviewed on 14 Aug 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
15 Oct - 20 Oct
found 14 hours ago
Return direct flight included
London (LON) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on 21 Jul 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
6 Oct - 11 Oct
found 24 hours ago
Return flight included
London (LHR) to Washington (WAS)
9.8/10 Exceptional! (28 reviews)
Staff was amazing. From the front desk to the restaurant. They made the short trip very enjoyable

Reviewed on 14 Aug 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
6 Oct - 11 Oct
found 24 hours ago
Return flight included
London (LHR) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on 12 Aug 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
6 Oct - 11 Oct
found 24 hours ago
Return flight included
London (LHR) to Washington (WAS)
9/10 Wonderful! (1,010 reviews)
it’s a good location

Reviewed on 12 Aug 2025

Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is £99 per night from 31 Aug to 1 Sept
£99
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Bed comfy, dinner delicious. Lovely ambiance in lobby and enjoyed pool."

Reviewed on 10 Aug 2025

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is £82 per night from 1 Sept to 2 Sept
£82
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,120 reviews)
"Liam was GREAT!! In addition to the young person that checked us in! This was a wonderful experience."

Reviewed on 12 Aug 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is £71 per night from 17 Aug to 18 Aug
£71
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Very nice staff, clean. Restaurant on premises with good bkfst"

Reviewed on 11 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 356 properties in Old Town Winchester
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Old Town Winchester travel package cost?
Maybe less than you imagined — from a low £640, as a matter of fact! By combining flights, hotels and car rentals into a tailor-made travel package, your trip to Old Town Winchester is just a few clicks away.
If I'm not able to travel, can I cancel my Old Town Winchester travel package?
It's hard to predict what the future holds, so it's comforting to know that you can change or cancel your Old Town Winchester travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Old Town Winchester?
If you love getting an amazing deal, bundle your bookings into an Old Town Winchester travel package. Whether you need flights, hotels, activities or rental cars, you can browse and book them all in one place. You'll have a wealth of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 properties all over the world to choose from. Fly with who you prefer, find a room where you like and save a tidy sum — now that's the perfect escape!
Does Expedia offer Book Now, Pay Later Old Town Winchester holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month works for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Old Town Winchester?
With interesting attractions like Winchester Medical Centre and Shenandoah University in this area, look for a hotel located near them. Apple Blossom Mall is another sight that pulls the crowds.
What are the top hotels in Old Town Winchester?
If this will be your first visit to Old Town Winchester, lock in a room at Travelodge by Wyndham Winchester or Holiday Inn Winchester Se-Historic Gateway, an IHG Hotel. Both hotels have good amenities and are popular options with many travellers.
How far in advance should I book my Old Town Winchester holiday?
It depends on the airline, but it's usually possible to browse through international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky travellers occasionally nab a cheaper ticket only weeks before the date of departure.
What does an Expedia Old Town Winchester travel package include?
With Expedia, you can choose a combination of hotels, car rentals and flights to create your ideal Old Town Winchester travel package. Once you've made your booking, you can add on the fun stuff like tours and activities. Remember — the more you bundle, the more dollars you'll save!
What should I know before booking an Old Town Winchester travel package?
When you book your flights, hotels and car rentals together, you'll score terrific discounts. Whether you're planning a rural escape in a cottage or want to stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with an Old Town Winchester Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to choose from across the world. With such a huge range of choice, finding the right carrier to whisk you away to Old Town Winchester shouldn't be hard.

Popular places to visit

Shenandoah Valley Discovery Museum

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.