Winchester Holidays from £903

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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.
Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was £1,181, price is now £903 per person
£903
per person
14 Jul - 19 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (790 reviews)
Spacious room with nice desk space and separate sitting area. Excellent breakfast The only problem was the lighting in the bathroom. The lights in front of the mirror were too dim and it was difficult to shave, put make-up on etc.

Reviewed on 5 May 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,343, price is now £959 per person
£959
per person
14 Jul - 19 Jul
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (1,165 reviews)
Beautiful hotel. They told us all in room supplies were free but there was only a few coffee pods there. Also, there was only 1 washcloth and 1 hand towel. At such a nice hotel I wouldn’t expect them to be chinch about supplies. We were also double charged for parking and they wouldn’t credit us for it without a receipt emailed to them, but we never received a receipt. we showed them the charge on our credit card app, but that wouldn’t suffice. Again, for such a nice hotel you would think they would just credit it.

Reviewed on 3 May 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was £1,242, price is now £955 per person
£955
per person
11 Jun - 15 Jun
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.2/10 Very Good! (1,002 reviews)
They don’t tell you that parking is not close, in a creepy parking lot, paying $45+$8 (parking tax for overnight parking)+1(parker membership)=$54 per night to park. There is a cool food hall nearby but that’s about it. The hotel accepts pets to keep that in mind.

Reviewed on 28 Apr 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was £1,125, price is now £911 per person
£911
per person
11 Jun - 15 Jun
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Great staff and a he beds were very comfortable

Reviewed on 21 Apr 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was £1,173, price is now £952 per person
£952
per person
11 Jun - 15 Jun
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
8.8/10 Excellent! (1,008 reviews)
I would highly recommend this hotel to anyone. The staff are nice and helpful when we had questions. The staff at Root &Vine when we order pizza's to take back to our room. The sercurity guards in the lobby would always say hi and ask how you are doing. The room was amazing and we enjoyed the view from our room.

Reviewed on 10 Apr 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 £67 per night from 27 May to 28 May
£67
27 May - 28 May
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
very nice hotel, very close to shopping and restaurants, and just off the interstate. Definitely would stay here again.

Reviewed on 6 May 2026

Spark by Hilton 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 £57 per night from 7 May to 8 May
£57
7 May - 8 May
includes taxes & fees
8.6/10 Excellent! (1,057 reviews)
Clean and comfortable. Good for the price.

Reviewed on 6 May 2026

Travelodge by Wyndham 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
The price is £109 per night from 17 May to 18 May
£109
17 May - 18 May
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
Staff was excellent- friendly, courteous. Helpful. Gym - small - but clean and most that you need. Pool - beautiful- on smaller side. Great bar vibe. Excellent location. This Wyndham so much better quality than the Wyndham we stayed at in Savannah, GA. Uno Pizzaria - connected to hotel - terrible ...

Reviewed on 2 May 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 2,041 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

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

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

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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.