Holiday Packages in Winchester, Virginia

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Tips for booking hotels in Winchester

Gain useful insights to help choose a hotel in Winchester. Data was last updated on Wed Jan 07 2026.
Cheapest month:July
Most expensive month:October
Average price in Winchester:£78/night
Cheapest price found:£28/night
Cheapest day:Friday
Most expensive day:Wednesday
£60 - £100
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£68 - £106
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Winchester vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Wed Jan 07 2026.
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

160 Front Royal Pike, Winchester, VA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£666
Avg. per night
View Deal
Hampton Inn Winchester-University/Mall Area
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

640 East Jubal Early Drive, Winchester, VA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£954
Avg. per night
View Deal
Hampton Inn Winchester N/Conference Center
Hampton Inn Winchester N/Conference Center

Hampton Inn Winchester N/Conference Center

1204 Berryville Avenue, Winchester, VA, United States
0.0 mi from city centre
Free Wi-Fi
Parking
£982
Avg. per night
View Deal
The George Washington - A Wyndham Grand Hotel
The George Washington - A Wyndham Grand Hotel

The George Washington - A Wyndham Grand Hotel

103 East Piccadilly Street, Winchester, VA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,079
Avg. per night
View Deal
Courtyard by Marriott Winchester Medical Center
Courtyard by Marriott Winchester Medical Center

Courtyard by Marriott Winchester Medical Center

300 Marriott Drive, Winchester, VA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£873
Avg. per night
View Deal
Holiday Inn Winchester Se-Historic Gateway By IHG
Holiday Inn Winchester Se-Historic Gateway By IHG

Holiday Inn Winchester Se-Historic Gateway By IHG

333 Front Royal Pike, Winchester, VA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£790
Avg. per night
View Deal
Hilton Garden Inn Winchester
Hilton Garden Inn Winchester

Hilton Garden Inn Winchester

120 Wingate Drive, Winchester, VA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£982
Avg. per night
View Deal
La Quinta by Wyndham Winchester
La Quinta by Wyndham Winchester

La Quinta by Wyndham Winchester

1055 Millwood Pike, Winchester, VA, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
£826
Avg. per night
View Deal
Motel 6 Winchester
Motel 6 Winchester

Motel 6 Winchester

2951 Valley Avenue, Winchester, VA, United States
0.0 mi from city centre
Free Wi-Fi
Air conditioning
£661
Avg. per night
View Deal
See all

Where to stay in Winchester

Utilise the map to find the perfect place to stay for your trip to Winchester. There are 39 hotels to choose from in Winchester.

FAQ about Winchester holiday packages

Find answers to frequently asked questions Cheapflights users have about Winchester holiday deals.

  • How much are vacation packages to Winchester?

    The cheapest price of a Winchester flight+hotel is currently £661.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Yes! Holidays on Cheapflights are designed to help users save money by bundling their flight, car rental, and hotel.

  • What other destinations does Winchester have flight+hotel deals to?

    Remember to check back often to keep track of all the enticing offers for holiday packages to Winchester and more.

Other popular holiday deals in Virginia

Consider booking a Flight+Hotel in one of these other areas of Virginia.
Virginia holidays
Norfolk holidays
Richmond holidays
Virginia Beach holidays
Charlottesville holidays
Woodbridge holidays
Arlington holidays
Newport News holidays
Williamsburg holidays
Alexandria holidays