Ashby Vacations from $276
Book a Hotel + Flight or Car together to unlock savings
Your Ashby Vacation
Lock in a custom vacation package to Ashby and get ready for your next big adventure. Stay in the neighborhood of Old Town Winchester, which is great for cafes and history, for a true taste of this vibrant city. Blue Ridge Shadows Golf Club and Shen-Val Farm Market are among the must-see sights to visit during a trip to Ashby. A few quick clicks is all it takes to craft a tailored Ashby vacation on Expedia.
The Latest Ashby vacation packages
Price found within the past 48 hours. Click for updated prices.
Furnished Apartments
Ashton Heights
$634
per person
Oct 15 - Oct 18
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
What to do in Ashby
Learning Lunch of Wine and Food Pairing with Winemaker Donna
$60
per adult
Ashby Hotel Deals
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
$77 nightly
$87 total
Sep 13 - Sep 14
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
$130 nightly
$148 total
Sep 8 - Sep 9
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
$104 nightly
$115 total
Sep 6 - Sep 7
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
"Coffee maker did not work."
Reviewed on Aug 31, 2026
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 Ashby Vacation Packages
Ashby Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Skyline Caverns, Chester Gap Cellars and Desert Rose Ranch & Winery |
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Frequently asked questions
How much does an Ashby vacation package cost?
You can grab a vacation package to this destination from $276 on Expedia. However, how much your vacation to Ashby costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ashby?
November, December and January are great times to search for cheap Ashby vacation packages. Choosing to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Ashby?
Usually, a handful of days is enough to go to the major sights during your Ashby vacation. However, if you prefer to have more time to kick back or take day trips, think about extending your itinerary.
How to find the best Ashby package deals?
Landing a cheap Ashby package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most economical Ashby package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashby vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights individually. Better still, you can tailor your Ashby getaway to fit 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 Ashby?
If you've got your Ashby vacation dates locked in, book as early as you can to grab some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ashby?
- Choose when to travel: Check your schedule and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to vacation in Ashby.
- Budget wisely: As well as the price of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Ashby.
- Discover Ashby using Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Ashby. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
- Work out your trip length: Consider how long you want to spend exploring Ashby. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Ashby vacation package.
- Book any activities or day trips: Here's the fun part — locking in everything you want to see and do. Explore some of the best things to do in Ashby and reserve your tickets early to save time (and maybe some cash too!).
Does Expedia offer Book Now, Pay Later Ashby vacation packages?
Your Ashby trip is meant to be an escape from your daily routine, not a reason for money worries. So to give you extra flexibility, we've partnered with online lender Affirm to offer you 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 are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.