Old Town Winchester Holidays from £741

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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.
Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
3 Sept - 9 Sept
found 13 hours ago
Return flight included
Glasgow (GLA) to Washington (DCA)
8.8/10 Excellent! (2,464 reviews)
Clean, excellent quality, friendly stuff. Restaurant is of an excellent quality, although maybe a little more expensive that I would expect. Good location for the purpose of my visit. Relatively far from the subway stations though; however buses are coming near.

Reviewed on 19 Jun 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
4 Sept - 11 Sept
found 13 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
10/10 Exceptional! (2 reviews)
My husband and I stayed here for our anniversary and it did not disappoint. We will definitely be coming back. The staff, the hotel, the restaurants- all absolutely amazing.

Reviewed on 22 Jun 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
3 Sept - 9 Sept
found 13 hours ago
Return flight included
Glasgow (GLA) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on 24 Jun 2025

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
4 Sept - 11 Sept
found 13 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
9.4/10 Exceptional! (1,444 reviews)
Perfect hotel and area.

Reviewed on 22 Jun 2025

Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
4 Sept - 11 Sept
found 13 hours ago
Return direct flight included
London (LGW) to Washington (DCA)
9.4/10 Exceptional! (1,001 reviews)
Excellent and exceptional. We actually extended our stay. It was fabulous.

Reviewed on 26 Jun 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 £105 per night from 7 Jul to 8 Jul
£105
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Great staff. Great location. Got nice quiet and spacious room. Easy walks to history, food and drink."

Reviewed on 14 Jun 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 7 Jul to 8 Jul
£82
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (2,068 reviews)
Would stay again!
"Very nice hotel. Super clean and comfortable. Friendly staff. Nice breakfast bar as well."

Reviewed on 23 Jun 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is £55 per night from 10 Jul to 11 Jul
£55
10 Jul - 11 Jul
includes taxes & fees
8.2/10 Very Good! (1,104 reviews)
"Very clean and eco-friendly…. Loved the waffles for breakfast!!!! Super bonus!!!"

Reviewed on 21 Jun 2025

Travelodge by Wyndham Winchester
See all 352 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 £741, 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

4/5(1 review)

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.