Ashby Vacations from $186

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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.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $407, price is now $186 per person
$186
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.

Reviewed on Nov 20, 2025

Hotel Ulysses, a Member of Design Hotels

Hotel Ulysses, a Member of Design Hotels

4 out of 5
Mount Vernon
Price was $413, price is now $192 per person
$192
per person
Jan 13 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (979 reviews)
Great customer service at front desk allowing early check in.

Reviewed on Dec 1, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $545, price is now $256 per person
$256
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
Dining room upgrade and staff are excellent

Reviewed on Nov 30, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $838, price is now $412 per person
$412
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,084 reviews)
Great hotel in an excellent location that is close to most museums

Reviewed on Nov 27, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $716, price is now $407 per person
$407
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,178 reviews)
The room was spacious with comfortable beds. The front desk and staff were nice and professional. I truly enjoyed my stay.

Reviewed on Dec 1, 2025

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Discover the most popular places to visit in Ashby

Front Royal Entrance Shenandoah National Park

4.5/5(178 reviews)

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

Front Royal Entrance Shenandoah National Park

Skyline Caverns

4.5/5(88 reviews)

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

Front Royal Visitor's Center

Rich with history, Front Royal Visitor's Center is a cultural attraction worth visiting in Front Royal. Stroll along the riverfront in this vibrant area, or seek out the hiking trails.

Front Royal Visitor's Center

What to do in Ashby

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
Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$16
per traveler
Shenandoah National Park Self-Guided Audio Tour
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
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
$93 nightly
The price is $101 total per night from Dec 4 to Dec 5
$101 total
Dec 4 - Dec 5
Total with taxes and fees
9.2/10 Wonderful! (2,237 reviews)
It was great

Reviewed on Nov 28, 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
$68 nightly
The price is $74 total per night from Dec 7 to Dec 8
$74 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (1,097 reviews)
Was congratulating myself on having chosen a nice, clean, simple place charging only $15 fee for each of my pets. Nice layout, smooth check in, pleasant staff. Until my better half pointed out the animal feces, dried and obviously a long-term resident, next to the bedside chair. Ed always leave tips ...

Reviewed on Nov 27, 2025

Travelodge by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $78 total per night from Dec 15 to Dec 16
$78 total
Dec 15 - Dec 16
Total with taxes and fees
9/10 Wonderful! (1,372 reviews)
Room and public areas were very clean and well taken care of.

Reviewed on Nov 26, 2025

Microtel Inn & Suites by Wyndham Winchester
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 $186 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.