Ashby Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Ashby Vacation Deals
Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
Southwest
CA $2,462
per person
Oct 3 - Oct 9
found 13 hours ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (1,215 reviews)
We had a wonderful stay at the InterContinental. The hotel is in a great location. We enjoyed being on the Wharf. The river view was wonderful, and there are many great restaurants within walking distance.
Reviewed on Aug 18, 2026
Club Quarters Hotel in Washington DC
Downtown Washington D.C.
CA $1,246
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (2,006 reviews)
I love it, perfect location, clan room, very kind staff, good air conditioning and public transportation near, definitely I will comeback¡¡
Reviewed on Aug 18, 2026
Ready to book your vacation to Ashby?
Ashby Hotel Deals
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
CA $110
CA $125 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
"When I arrived D at the front desk was so helpful to me! She was very professional in her job answering all my questions to her. The room I stayed in was very clean. Breakfast was really good too! Overall experience 10 of 10!"
Reviewed on Aug 18, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
CA $129
CA $148 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"It was a convenient location and having on-site dining was a plus for us. The room was clean and comfortable and the staff was very friendly."
Reviewed on Aug 18, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
CA $170
CA $192 total
Aug 27 - Aug 28
includes taxes & fees
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.
What to do in Ashby
Shenandoah National Park Self-Guided Driving Audio Tour
CA $24
per traveller
100% of travellers recommend
Learning Lunch of Wine and Food Pairing with Winemaker Donna
CA $85
per adult
Frequently asked questions
How much does an Ashby vacation package cost?
You can pick up a vacation package to this destination from CA $1,131 on Expedia. However, how much your vacation to Ashby costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Ashby?
If you'd like to snag a cheap Ashby vacation package, consider travelling in January, February and November. You'll generally find better prices on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Ashby?
Typically, a handful of days is enough to check out the major attractions during your Ashby vacation. However, if you want to have some time to chill out or go on day trips, think about extending your trip.
How to find the best Ashby package deals?
Landing a cheap Ashby package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most economical Ashby package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Ashby vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Ashby getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Ashby?
If you have your Ashby travel dates confirmed, book as early as you can to grab some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Ashby?
- Choose your dates: The things you plan to do in Ashby and your preferred season will help you decide when to get away.
- Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will probably be the biggest expense during your trip to Ashby.
- Set the duration of your trip: Start by making a list of all the activities and sights you want to get to in Ashby. Then, estimate how long you'll need for each, including any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Ashby vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
