Ashby Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Ashby

TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 26 Jul to 27 Jul
S$131
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,035 reviews)
"A clean room and a comfy bed, friendly staff, and the right location for me."

Reviewed on 15 Jul, 2026

TRU By Hilton 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$123 per night from 2 Aug to 3 Aug
S$123
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Clean room, good room amenities. Could use a few more outdoor seating options."

Reviewed on 15 Jul, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 6 Aug to 7 Aug
S$179
6 Aug - 7 Aug
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Best hotel I’ve stayed in!! Will definitely be booking again each visit to Pa from SC! Clean and classy rooms/bathrooms. Historic charm yet updated/maintained. No jail quality sheets/towels, staff was great, pool and hot tub felt more spa like then traditional indoor hotel pool! Just all around wonderful ..."

Reviewed on 15 Jul, 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 462 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

Savor our unique Blue Ridge Mountain Views

Relax and Unwind at The Blue Ridge Retreat

S$504
per adult
Relax and Unwind at The Blue Ridge Retreat
Indulge in Flavor: A delightful lunch plate featuring three scrumptious sliders including, a savory roast beef slider, chicken and salmon sliders, Then! A sweet finish with dessert and tasty truffles!

Learning Lunch of Wine and Food Pairing with Winemaker Donna

S$77
per adult
Learning Lunch of Wine and Food Pairing with Winemaker Donna
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.

Explore a world of travel with Expedia

* 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.