Old Town Winchester Holidays from £966

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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.
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
Price was £1,324, price is now £966 per person
£966
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)
Expected better from crown plaza

Reviewed on 30 Jun 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £2,496, price is now £1,661 per person
£1,661
per person
14 Sept - 21 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9/10 Wonderful! (1,199 reviews)
Definitely think this hotel should be labeled 3 or 4 stars instead of 5. How wore down it looks in like the elevators and certain places. Staff super friendly though! Love free the coffee and unique selection of teas but that area was always quite messy and no trash can to throw away items in that area even though I brought it to their attention prior that the trash can was missing.. not sure if its worth 40 dollar a day amenity fee prob wont stay at this location in the future

Reviewed on 1 Jul 2026

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Price was £1,568, price is now £1,106 per person
£1,106
per person
14 Sept - 21 Sept
found 15 hours ago
Return direct flight included
London (LGW) to Baltimore (BWI)
8.8/10 Excellent! (1,901 reviews)
Next door to the Metro. Good coffee.. Friendly staff. Small rooms..Very cozy beds..

Reviewed on 1 Jul 2026

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was £1,467, price is now £1,037 per person
£1,037
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,691 reviews)
Great location , super clean and great staff !

Reviewed on 29 Jun 2026

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was £2,867, price is now £2,045 per person
£2,045
per person
22 Sept - 29 Sept
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.8/10 Exceptional! (1,001 reviews)
Great staff. Very approachable and helpful.

Reviewed on 28 Jun 2026

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 £104 per night from 16 Jul to 17 Jul
£104
16 Jul - 17 Jul
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Cool historic hotel! Very clean and nice!"

Reviewed on 1 Jul 2026

The George Washington Hotel, A Wyndham Grand Hotel
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is £74 per night from 2 Aug to 3 Aug
£74
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 Jun 2026

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is £77 per night from 26 Jul to 27 Jul
£77
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"Very inviting front desk lobby. Staff was friendly and courteous. Area by lobby had information on area restaurants, things to do, very helpful."

Reviewed on 2 Jul 2026

TRU By Hilton Winchester
See all 372 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.
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Frequently asked questions

How much does an Old Town Winchester travel package cost?
Maybe less than you imagined — from a low £966, 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.

Stay near popular Old Town Winchester attractions

Shenandoah Valley Discovery Museum

8.6/10 (78 reviews)
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.
See properties

* 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.