Ashby Vacations from $438

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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.

The Latest Ashby vacation packages

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
Price was $692, price is now $438 per person
$438
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Staff was professional, helpful, and friendly!

Reviewed on Feb 16, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $1,137, price is now $725 per person
$725
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,001 reviews)
Nice room and a short walk to bars and restaurants

Reviewed on Feb 24, 2026

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $832, price is now $534 per person
$534
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.6/10 Excellent! (1,002 reviews)
Clean room staff was great

Reviewed on Mar 3, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $969, price is now $647 per person
$647
per person
May 28 - May 30
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Great location, hotel was beautiful and staff was very friendly.

Reviewed on Feb 24, 2026

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $924, price is now $619 per person
$619
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,835 reviews)
Carpets are very dirty with stains, nasty carpet Someone was vacuum cleaning after 9pm, and neighbors room was screaming late night. I had a busy trip and was looking forward to rest and have my sleep, but unfortunately the amount of noise was unbearable.

Reviewed on Mar 2, 2026

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Discover the most popular places to visit in Ashby

Image depicts a view of Carlsbad Caverns in New Mexico, shrouded in an ethereal mist

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.

Skyline Caverns
Panoramic View of Shenandoah National Park Overlook from Dickey Ridge Visitor Center

Dickey Ridge Visitor Center

Explore the great outdoors at Dickey Ridge Visitor Center, a lovely green space in Front Royal. Discover the mountain views in this vibrant area, or seek out the hiking trails.

Dickey Ridge Visitor Center

Front Royal Entrance Shenandoah National Park

Explore the great outdoors at Front Royal Entrance Shenandoah National Park, a lovely green space in Front Royal. While in this family-friendly area, you can savor the top-notch restaurants.

Front Royal Entrance Shenandoah National Park

What to do in Ashby

Appalachia Audio Tour Bundle Experience

Appalachia Self-Guided Tour Bundle

$35
per traveler
Appalachia Self-Guided Tour Bundle
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

$60
per adult
Learning Lunch of Wine and Food Pairing with Winemaker Donna
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

$60
per adult
Wine Bootcamp - Led by our winemaker
See all activities in Ashby

Ashby Hotel Deals

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
$109 nightly
The price is $119 total per night from Mar 5 to Mar 6
$119 total
Mar 5 - Mar 6
Total with taxes and fees
9.2/10 Wonderful! (2,280 reviews)
Clean room. Comfortable bed. Easy in and out. Reasonably close to Old Town Winchester in historic district. Friendly staff.

Reviewed on Mar 1, 2026

La Quinta Inn & Suites by Wyndham Winchester
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
$122 nightly
The price is $138 total per night from Mar 9 to Mar 10
$138 total
Mar 9 - Mar 10
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
Room was clean but a lil noisy. We didn't have the best room location. Must have been close to a staff area

Reviewed on Mar 2, 2026

The George Washington Hotel, A Wyndham Grand Hotel
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
Fully refundable
$80 nightly
The price is $87 total per night from Mar 23 to Mar 24
$87 total
Mar 23 - Mar 24
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
Hotel needs updating and repair. Had hole in bathroom door and securiity latch was broken.

Reviewed on Feb 23, 2026

Sleep Inn & Suites Winchester near University
See all 457 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.

Find the Best Ashby Vacation Packages

Ashby Essential Information

Language
English
Currency
U.S dollars
Top Sights
Skyline Caverns, Chester Gap Cellars and Desert Rose Ranch & Winery

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Frequently asked questions

How much does an Ashby vacation package cost?
You can grab a vacation package to this destination from $438 on Expedia. However, how much your vacation to Ashby costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Ashby?
November, December and January are great times to search for cheap Ashby vacation packages. Choosing to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Ashby?
Usually, a handful of days is enough to go to the major sights during your Ashby vacation. However, if you prefer to have more time to kick back or take day trips, think about extending your itinerary.
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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Ashby vacation as a package?
An Expedia vacation 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 vacation package to Ashby?
If you've got your Ashby vacation 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. Choose when to travel: Check your schedule and get your bags packed. Your favorite time of year and the activities on offer will also help you decide when to vacation in Ashby.
  2. Budget wisely: As well as the price of your hotel, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Ashby.
  3. Discover Ashby using Expedia's trip planning tool: Gain insights into the leading attractions and best properties for your trip to Ashby. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Work out your trip length: Consider how long you want to spend exploring Ashby. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Ashby vacation package.
  6. Book any activities or day trips: Here's the fun part — locking in everything you want to see and do. Explore some of the best things to do in Ashby and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Ashby vacation packages?
Your Ashby trip is meant to be an escape from your daily routine, not a reason for money worries. So to give you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.