Gainesboro Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Gainesboro
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundable
The price is 2.374.848 ₫ per night from 24 Jun to 25 Jun
2.374.848 ₫
2.690.704 ₫ total
24 Jun - 25 Jun
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"The room was clean and very comfortable and parking was on site"
Reviewed on 5 Jun 2026
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is 2.755.485 ₫ per night from 5 Jul to 6 Jul
2.755.485 ₫
3.039.355 ₫ total
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (910 reviews)
"great visit and would stay again for sure"
Reviewed on 4 Jun 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is 1.869.643 ₫ per night from 7 Jun to 8 Jun
1.869.643 ₫
2.034.224 ₫ total
7 Jun - 8 Jun
includes taxes & fees
8.6/10 Excellent! (1,055 reviews)
"The room was very clean and the staff was friendly."
Reviewed on 2 Jun 2026
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.
Popular places to visit
Museum of the Shenandoah Valley
You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Jim Barnett Park
Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.
Shenandoah University
Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.
