Gainesboro Vacations from $332

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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 $692, price is now $332 per person
$332
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8/10 Very Good! (1,178 reviews)
No hot water in the morning. Very quick shower

Reviewed on Dec 13, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,047, price is now $540 per person
$540
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,084 reviews)
We loved our stay at the Sofitel. Very clean and very conveniently located. The staff was very welcoming and absolutely nice. We were at first given a junior suite on the 12th floor. The heating unit was too loud and unbearable, they immediately sent someone to inspect it and - given that there was no working around it - they moved us to another suite and - without asking - they included next morning complimentary breakfast at their wonderful Opaline Restaurant. Yes 5 stars!

Reviewed on Dec 12, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
Price was $850, price is now $474 per person
$474
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,603 reviews)
The room was well-appointed with some thoughtful touches that made a longer stay more comfortable. The gym was better than an average hotel gym. The location is convenient to Dupont Circle, and I'd definitely stay again.

Reviewed on Dec 10, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $637, price is now $365 per person
$365
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
Exceptionally friendly and accommodating staff.

Reviewed on Dec 10, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
Price was $895, price is now $522 per person
$522
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,059 reviews)
As always, the staff at the Watergate is warm and welcoming. The rooms are immaculate and the food is amazing.

Reviewed on Dec 2, 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 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

Hampton Inn Martinsburg

Hampton Inn Martinsburg

2.5 out of 5
975 Foxcroft Ave Martinsburg WV
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Dec 21 to Dec 22
$94 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Room fabulous, staff superior , breakfast great

Reviewed on Dec 11, 2025

Hampton Inn Martinsburg
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
$73 nightly
The price is $79 total per night from Jan 7 to Jan 8
$79 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
9/10 Wonderful! (1,375 reviews)
Everything was great. Had to leave early in the morning because of a snowy weather forecast- missed breakfast.

Reviewed on Dec 7, 2025

Microtel Inn & Suites by Wyndham Winchester
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 Jan 11 to Jan 12
$112 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,221 reviews)
Comfortable and clean room.

Reviewed on Dec 9, 2025

La Quinta Inn & Suites by Wyndham Winchester
See all 322 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 $332 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.