Winchester Holidays from £760

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Your Winchester Holiday

The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester holiday package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organising your ultimate tailored Winchester holiday is easy with Expedia.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was £1,007, price is now £760 per person
£760
per person
6 Sept - 13 Sept
found 21 hours ago
Return flight included
London (LON) to Baltimore (BWI)
8.8/10 Excellent! (1,033 reviews)
We love our stay at this hotel. So well located. The staff was friendly specially Deborah. Breakfast was second to none. Great quality ingredients and the price accordly to the area so I recommend it prepay the breakfast. Thank you the lady what serve our breakfast every day, she was super kind and professional.

Reviewed on 23 Jun 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,739, price is now £1,272 per person
£1,272
per person
31 Jul - 7 Aug
found 1 day ago
Return direct flight included
Birmingham (BHX) to Baltimore (BWI)
9/10 Wonderful! (1,194 reviews)
Location and access to the sights and attractions of DC is great! Everything is within walking distance.

Reviewed on 23 Jun 2026

Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Price was £1,303, price is now £970 per person
£970
per person
6 Sept - 13 Sept
found 21 hours ago
Return flight included
London (LON) to Baltimore (BWI)
9.2/10 Wonderful! (1,295 reviews)
Very clean, huge rooms, excellent location. Free laundry facilities were available.

Reviewed on 22 Jun 2026

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was £1,139, price is now £879 per person
£879
per person
6 Sept - 13 Sept
found 21 hours ago
Return flight included
London (LON) to Baltimore (BWI)
9.2/10 Wonderful! (1,012 reviews)
Location and staff were great. That’s about it.

Reviewed on 20 Jun 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was £1,279, price is now £1,013 per person
£1,013
per person
29 Jul - 5 Aug
found 23 hours ago
Return flight included
London (LON) to Baltimore (BWI)
8.8/10 Excellent! (1,004 reviews)
Property is clean but well overdue for updates. The room was old and dated. It had a broken bathroom vanity and our AC was barely working. AC required multiple resets to get it to blow cold air, it was extremely loud when it turned on, and required to be reset multiple times throughout our 3 nights there. When informed of the poorly working AC, staff offered very minimal solutions. No on was on site to fix the issue, no room change offered and no compensation offered. No follow up was done with us to ensure that the issue had been fixed after we informed them we were able to reset our AC ourselves. Would definitely not stay again.

Reviewed on 18 Jun 2026

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
27,300
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre

Top hotels in Winchester

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 £82 per night from 28 Jun to 29 Jun
£82
28 Jun - 29 Jun
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Staff was friendly and responsive. Room was clean. We did not use amenities, but they seemed nice enough"

Reviewed on 21 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 £65 per night from 7 Jul to 8 Jul
£65
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (979 reviews)
"It was the cleanest hotel I have ever stayed at. The property was well maintained. Free breakfast was good. I will stay there every time I pass through Winchester. The hotel looked like it was built and opened yesterday. Lol! Maybe that’s why everything was so clean. Only time will tell. And the ..."

Reviewed on 23 Jun 2026

TRU By Hilton 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 £112 per night from 7 Jul to 8 Jul
£112
7 Jul - 8 Jul
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Enjoyed the stay here for a weekend exploring the Shenandoah Valley."

Reviewed on 23 Jun 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 2,088 properties in 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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Popular places to visit

Apple Blossom Mall

You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Apple Blossom Mall

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

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

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* 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.