Ashby Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Ashby

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
The price is S$162 per night from 24 Jul to 25 Jul
S$162
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (2,082 reviews)
Highly recommend
"Hotel was very clean and comfortable. Staff were friendly and helpful. It was very quiet, we didn’t heard anyone. Will definitely stay again if in the area!"

Reviewed on 20 Jul, 2025

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 23 Jul to 24 Jul
S$97
23 Jul - 24 Jul
includes taxes & fees
8.4/10 Very Good! (1,090 reviews)
"Close to Sportsman 's Warehouse. Short drive to Chick-fil-A. Breakfast was good, as we like a light meal. Room was quiet, slept well on comfy bed."

Reviewed on 17 Jul, 2025

Travelodge by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is S$134 per night from 3 Aug to 4 Aug
S$134
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,013 reviews)
"I loved this hotel! The property is very clean and the employees are professional, willing to go above and beyond for their customers and kind which can be a rarety these days. I liked the restaurant on site Kem's, the food is good and the employees are nice and helpful. The only two things that ..."

Reviewed on 20 Jul, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 440 properties in Ashby
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

Shenandoah National Park Self-Guided Driving Audio Tour

S$22
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

S$20
per traveller
Shenandoah National Park Self-Guided Audio Tour
You'll gain a solid knowledge of wine basics, pairing concepts, and tasting techniques, enabling you to explore and savor wines with a newfound expertise. Cheers to a voyage of flavor and discovery!

Wine Bootcamp - Led by our winemaker

S$77
per adult
Wine Bootcamp - Led by our winemaker
See all activities in Ashby

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.