
Gainesboro Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Gainesboro Holiday
Come and experience this captivating city for yourself with a Gainesboro holiday package. Think about staying in the neighbourhood of Shawnee Land, which is great for hiking and nature, and your time here will be nothing short of unforgettable. Eager to sightsee? Spend your days exploring well-known attractions like Rocking S Ranch during your trip to Gainesboro. Expedia has what you need to escape your routine. Tailor your holiday to Gainesboro to suit your travel style, whatever that may be.
Gainesboro Holiday
Gainesboro Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre |
Our pick of the best Gainesboro Hotel Deals

La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 29 Sept to 30 Sept
AU$179
29 Sept - 30 Sept
includes taxes & fees
9.2/10 Wonderful! (2,152 reviews)
"Easy access to the highway as we passed through."
Reviewed on 13 Sept 2025

Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 29 Sept to 30 Sept
AU$143
29 Sept - 30 Sept
includes taxes & fees
9/10 Wonderful! (1,342 reviews)
"Close to route 81"
Reviewed on 19 Sept 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is AU$158 per night from 28 Sept to 29 Sept
AU$158
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Excellent hotel.
"The hotel was very nice and the staff was great! Check-in was easy and very helpful. We had our breakfast included which worked out well. Tina, our server, was above and beyond. She was so friendly and offered my husband a few suggestions which was wonderful. Highly recommend anyone staying ..."
Reviewed on 16 Sept 2025
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.
Discover the most popular places to visit in Gainesboro
George Washington's Office
You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.