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.
Arlo Washington DC
Northwest
CA $815
per person
Nov 10 - Nov 14
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (2,095 reviews)
The breakfast was mediocre. Not many options available, and entirely pork based. As someone who cannot consume pork
Reviewed on Oct 3, 2026
Ready to book your vacation to Ashby?
Ashby Hotel Deals
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
CA $131
CA $146 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,444 reviews)
"The room was clean but we picked this hotel so we could use the pool which was very dirty. Piles of dirt in every corner and water was quite cool. Room was clean and beds were comfortable. Bathroom very tight. Alarm on radio was set and woke us up at 3 AM! We passed on breakfast didn’t look too ..."
Reviewed on Oct 3, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
CA $185
CA $210 total
Oct 28 - Oct 29
includes taxes & fees
TRU By Hilton Winchester
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
CA $127
CA $141 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Stay was nice for 1 night. If it would have been longer it wouldn’t have been ideal. Can easily hear rooms next door."
Reviewed on Oct 3, 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.
What to do in Ashby
Learning Lunch of Wine and Food Pairing with Winemaker Donna
CA $84
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 $811 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.
