Ashby Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Ashby
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
S$111
28 Sept - 29 Sept
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
S$176
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Really love this hotel. A bit more luxury with reasonable rates. The rooms are clean, comfortable and well maintained. Onsite bar and restaurant but also many other restaurants, cafes and pubs within walking distance. Ritual Spa onsite is awesome. You have to pay daily for parking but worth the convenience ..."
Reviewed on 31 Aug, 2026
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
S$147
3 Sept - 4 Sept
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Coffee maker did not work."
Reviewed on 31 Aug, 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
S$78
per adult
Frequently asked questions
How much does an Ashby holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Ashby costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ashby?
January, February and November are the best times to look for cheap Ashby holiday packages. Choosing to travel in quieter periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Ashby?
The ideal length of your Ashby holiday depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to tick off all the leading sights and explore some hidden spots along the way.
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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashby holiday as a package?
An Expedia holiday 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 holiday package to Ashby?
If you've got your Ashby holiday 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?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Ashby.
- Work out your budget: Make sure you have enough money to cover everything from transportation and meals to activities and flights. Your accommodation will likely be the biggest expense during your trip to Ashby.
- Decide how long to go away for: Now that you're more familiar with Ashby, you can work out the perfect length of your holiday. Create a rough plan and allocate enough time to cover everything you want to see.
- Combine your accommodation and airfare: Once you've nailed down your trip dates and duration, lock in the perfect Ashby holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
