Gainesboro Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Gainesboro

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 P3,887 per night from Jul 10 to Jul 11
P3,887
P4,230 total
Jul 10 - Jul 11
includes taxes & fees
8.2/10 Very Good! (1,110 reviews)
No frills, but clean
"The hotel room was clean no frills, the floor was wet when we got in there. It was a dark brown linoleum. I don’t know why it was wet. Room is acceptable just as stated no-frills."

Reviewed on Jun 28, 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG
Holiday Inn Winchester Se-Historic Gateway by IHG
3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is P5,239 per night from Jul 6 to Jul 7
P5,239
P5,869 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"It’s a lovely property. Clean, updated, and friendly staff."

Reviewed on Jun 30, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is P6,186 per night from Jul 10 to Jul 11
P6,186
P6,730 total
Jul 10 - Jul 11
includes taxes & fees
9/10 Wonderful! (2,071 reviews)
"Clean spacious nice staff"

Reviewed on Jun 27, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 326 properties in Gainesboro
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.

Frequently asked questions

How much does a Gainesboro vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Gainesboro costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Gainesboro?
You can typically find reduced prices and greater availability in January, February and November. Take a look at our cheap Gainesboro vacation packages and you could score some great off-season deals.
How many days is enough for Gainesboro?
The ideal length for your Gainesboro vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to tick off all the major sights and explore some hidden spots along the way.
How to find the best Gainesboro package deals?
Landing a cheap Gainesboro package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Gainesboro package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Gainesboro vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can personalize your Gainesboro getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Gainesboro?
Enjoy amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Gainesboro break.
How to plan a trip to Gainesboro?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the type of activities available will also help you decide when to vacation in Gainesboro.
  2. Set a budget: Consider expenses such as flights, transportation and food when calculating how much to put aside for your trip to Gainesboro. Then, pick a hotel that works with your budget, whether that's an economical option or a high-end retreat.
  3. Decide how long to go for: Now that you know more about Gainesboro, you can work out the ideal length of your break. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Gainesboro vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.