Ashby Holidays from AU$834
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
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
Your Ashby Holiday
Create a custom holiday package to Ashby and get ready for your next great escape. Base yourself in the neighbourhood of Old Town Winchester, which is good for cafes and history, for a real taste of this captivating city. Be sure to do some sightseeing during your trip to Ashby. Blue Ridge Shadows Golf Club and Shen-Val Farm Market are some leading attractions to check out. A few quick clicks is all it takes to create your perfect Ashby holiday on Expedia.
The Latest Ashby Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The St. Gregory Hotel
Downtown Washington D.C.
Save 100% on your flight
per person
23 Sept - 27 Sept
found 6 hours ago
Return flight included
Toronto (YYZ) to Washington (DCA)
8.6/10 Excellent! (1,007 reviews)
Lovely property and super friendly bar staff! The room was great, too. Unfortunately I booked the room with the intention of pushing a major project across the finish line in the quiet of my room, but there was no internet the entire time I was there and no electricity on the morning of departure (no fault of their own as the entire city block lost power).
Reviewed on 21 Jul. 2025
Ashby Holiday
Ashby Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 7ºC |
Max Temp Summer | 29ºC |
Top Sights | Skyline Caverns, Chester Gap Cellars and Desert Rose Ranch & Winery |
Our pick of the best Ashby Hotel Deals
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$194 per night from 23 July to 24 July
AU$194
23 July - 24 July
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
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 27 July to 28 July
AU$119
27 July - 28 July
includes taxes & fees
8.4/10 Very Good! (1,089 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
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is AU$160 per night from 3 Aug to 4 Aug
AU$160
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Staff was super nice when checking in!"
Reviewed on 15 Jul. 2025
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.
Discover the most popular places to visit in Ashby
Skyline Caverns
Explore the great outdoors at Skyline Caverns, a lovely green space in Front Royal. Stroll along the riverfront in this vibrant area or seek out the hiking trails.
What to do in Ashby
Explore America's Best: 30+ National Parks Self-Guided Bundle
AU$229
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
AU$26
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Audio Tour
AU$24
per traveller
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.