Gainesboro Vacations from $247

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Your Gainesboro Vacation

Come and experience this amazing city for yourself with a Gainesboro vacation package. Consider staying in the neighborhood of Shawnee Land, which is great for hiking and nature, and your time here is sure to be unforgettable. Any trip to Gainesboro has to include some sightseeing. Rocking S Ranch is an excellent place to begin exploring. Expedia is here to help you escape the everyday. Tailor your vacation to Gainesboro to match your travel style, whatever that may look like.

The Latest Gainesboro vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn & Suites by Wyndham Laurel Near Fort Meade

Days Inn & Suites by Wyndham Laurel Near Fort Meade

2 out of 5
North Laurel
Save 100% on your flight
per person
Aug 11 - Aug 17
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
7/10 Good! (1,008 reviews)
Front desk customer service was excellent! I've definitely recommended a boost in your ratings as it appears you have been unfairly rated.

Reviewed on Jun 27, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
10/10 Exceptional! (3 reviews)
Very difficult to pull up and take advantage of valet parking. Otherwise, everything was AMAZING!

Reviewed on Jun 29, 2025

Element Arundel Mills BWI Airport

Element Arundel Mills BWI Airport

3 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 17
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Shower was banged up with cracks in wall and handle fell off when I grabbed it.

Reviewed on Jul 8, 2025

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
Save 100% on your flight
per person
Aug 11 - Aug 17
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (573 reviews)
The hotel was nice I wish that it had a gym and better pillows but it was overall great.

Reviewed on Jul 5, 2025

Hotel Revival Baltimore

Hotel Revival Baltimore

4 out of 5
Mount Vernon
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,007 reviews)
The property and the hotel was great.

Reviewed on Jul 9, 2025

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Discover the most popular places to visit in Gainesboro

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Staircase at Handley Library

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Handley Regional Library

Shenandoah University

4.5/5(69 reviews)

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah University

Gainesboro Hotel Deals

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
$69 nightly
The price is $75 total per night from Jul 14 to Jul 15
$75 total
Jul 14 - Jul 15
Total includes taxes and fees
8.4/10 Very Good! (1,096 reviews)
"The stay was relaxing, as I didn't have to stress about uncleanliness. And the breakfast was very nice."

Reviewed on Jul 8, 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
$96 nightly
The price is $104 total per night from Jul 20 to Jul 21
$104 total
Jul 20 - Jul 21
Total includes taxes and fees
9/10 Wonderful! (1,000 reviews)
"The shower floor could be upgraded and I wish there was not carpet in room but other then that it was great! We will stay again! Breakfast was excellent and the bar/restaurant was open until 9pm and that was on July 4th holiday!"

Reviewed on Jul 6, 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
$116 nightly
The price is $126 total per night from Jul 13 to Jul 14
$126 total
Jul 13 - Jul 14
Total includes taxes and fees
9/10 Wonderful! (2,077 reviews)
"Every thing was great . Definitely will come again"

Reviewed on Jul 5, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 321 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.

Find the Best Gainesboro Vacation Packages

Gainesboro Essential Information

Language
English
Currency
U.S dollars
Top Sights
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater

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Frequently asked questions

How much does a Gainesboro vacation package cost?
You can snap up a vacation package to this destination from $247 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?
If you're hoping to snag a cheap Gainesboro vacation package, consider visiting in December, January and February. You'll generally find better prices on flights and hotels during these quieter months --- perfect for budget-conscious travelers.
How many days is enough for Gainesboro?
Typically, a handful of days is enough to see the main sights during your Gainesboro vacation. But if you want to have some time to unwind or go on day tours, consider extending your trip.
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.
Does Expedia offer Book Now, Pay Later Gainesboro vacation packages?
Your Gainesboro getaway should be an escape from your daily routine, not a source of money-related stress. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.