Ashby Vacation Packages
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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.
Top Ashby Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kimpton Banneker Hotel by IHG
Downtown Washington D.C.
Price was CA $1,479, price is now CA $1,117 per person
CA $1,117
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (799 reviews)
Friendly, family atmosphere. Everybody was so kind and helpful and all the staff was greeting us as long-time friends from day 1. They were so sincere and engaged in conversations with us and all the other guests. One of the best hotels we stayed in, it is going to be on the top of our list for our next trip to WAS.
Reviewed on May 8, 2026
Salamander Washington DC
Southwest
Price was CA $1,982, price is now CA $1,381 per person
CA $1,381
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,089 reviews)
Rooms over rail tracks would benefit from additional sound-proofing but otherwise fantastic stay
Reviewed on May 7, 2026
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Price was CA $1,576, price is now CA $1,131 per person
CA $1,131
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Great staff and a he beds were very comfortable
Reviewed on Apr 21, 2026
The Watergate Hotel
Northwest
Price was CA $1,547, price is now CA $1,139 per person
CA $1,139
per person
Jun 13 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,141 reviews)
Amazing pool area, hot tub, and sauna! Honestly, it was so good that it is all I remember about the hotel and I will definitely be back! We went at Valentine's Day and they also have an amazing restaurant experience!
Reviewed on May 8, 2026
The Jefferson, Washington, DC
Downtown Washington D.C.
Price was CA $2,477, price is now CA $1,868 per person
CA $1,868
per person
Jun 15 - Jun 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.8/10 Exceptional! (1,004 reviews)
Charming hotel and very friendly staff especially during check-in. My one and only complaint is how noisy my stay was. I highly recommend asking for a room far away from the house-keeping closet space because they are constantly in and out and shutting doors at all hours of the day. The doors to the rooms need to be sealed better but I understand it's an older hotel.
Reviewed on May 5, 2026
Ashby Hotel Deals
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from May 31 to Jun 1
CA $114
CA $130 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,029 reviews)
It was a nice hotel and very worth the price we paid! The Continental breakfast was great and had a lot of choices. The staff was very attentive as well.
Reviewed on May 7, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from May 25 to May 26
CA $97
CA $106 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,059 reviews)
Air conditioning and heat worked properly, and easy to use. I like that the door to room has an alarm if door is left open. I love the big parking lot and design. Great for semi's, RV's, etc. Staff was so friendly and helpful at daytime front desk. I love the pull-down shades verses curtains. It ...
Reviewed on May 8, 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from May 17 to May 18
CA $178
CA $202 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
Toilets are low
Reviewed on May 7, 2026
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.
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.
What to do in Ashby
Great Smoky & Shenandoah National Park Driving Audio Tour
CA $33
per traveller
Shenandoah National Park Self-Guided Driving Audio Tour
CA $23
per traveller
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
