Gainesboro Vacations from $147

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was $306, price is now $147 per person
$147
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (1,012 reviews)
You have to pay for the parking even though the parking lot empty and there are not many cars

Reviewed on Aug 26, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was $975, price is now $458 per person
$458
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.6/10 Excellent! (1,008 reviews)
Nicely renovated and great staff

Reviewed on Aug 28, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $433, price is now $245 per person
$245
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.2/10 Very Good! (2,066 reviews)
The property was very clean. The agents were helpful. On checking in, our room couch had a stain on it. We really didnt want to sit on it. We needed to call the desk to report the problem but i phone didn't work. We had to go to the desk to report the problem. They told us that the phone was hsving network problems but it was not fixed before we left. We also had a problem casting to the tv. We had to go down to the desk agent and report problem because our phone didn't work. Very disappointing stay.

Reviewed on Aug 28, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $379, price is now $217 per person
$217
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,006 reviews)
Convenient external room door made it easy walking my dog. Did not have to walk thru.obby.

Reviewed on Aug 24, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $943, price is now $551 per person
$551
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful place! Amazing staff!

Reviewed on Aug 21, 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 top-notch restaurants or charming coffeehouses 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 top-notch restaurants or charming coffeehouses in this walkable area.

Handley Regional Library

Winchester Medical Center

4/5(39 reviews)

Though Winchester Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Winchester while you are here.

Winchester Medical Center

Gainesboro Hotel Deals

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
$103 nightly
The price is $112 total per night from Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on Aug 25, 2025

La Quinta Inn & Suites 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
$85 nightly
The price is $92 total per night from Sep 1 to Sep 2
$92 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Clean and staff was great."

Reviewed on Aug 23, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $86 total per night from Sep 15 to Sep 16
$86 total
Sep 15 - Sep 16
Total with taxes and fees
9/10 Wonderful! (1,326 reviews)
"It was a great experiencia. It was really clean and the staff was exactly friendly and accommodated"

Reviewed on Aug 24, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 327 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.

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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 $147 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.