Chestnut Springs Vacations from $449
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chestnut Springs Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Shenandoah Wilderness Traveler
Price was $640, price is now $449 per person
$449
per person
Jan 22 - Jan 27
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Charlottesville (CHO)
8.6/10 Excellent! (65 reviews)
It was a lodge and it was picturesque on water and all around. It was pastures full of beautiful horses. The rooms were really small but they worked and the one thing that I was surprised is when I paid through Expedia I thought I was paid 100% but when I got there, they charge a $25 per day resort fee. Because they also have an RV and cabins and they have a playground basketball court things like that so I guess they charge a resort fee personally it should just be part of the rental so you’re not getting any surprise charges when you get there, otherwise it was lovely and I would actually consider going back there.
Reviewed on Oct 21, 2025
Little Mod Hotel at the University
Venable
Save 100% on your flight
Price was $882, price is now $554 per person
$554
per person
Jan 22 - Jan 27
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Charlottesville (CHO)
9.2/10 Wonderful! (281 reviews)
All of the above. Super friendly and helpful front desk!
Reviewed on Nov 13, 2025
Oakhurst Inn at the University
Jefferson Park Avenue
Save 100% on your flight
Price was $927, price is now $603 per person
$603
per person
Jan 22 - Jan 27
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Clean room. Staff was very accommodating when the temperature in the room was too warm.
Reviewed on Nov 7, 2025
The Draftsman, Charlottesville, University, Autograph Collection Hotel
10th and Page
Save 100% on your flight
Price was $917, price is now $615 per person
$615
per person
Jan 22 - Jan 27
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Charlottesville (CHO)
9.4/10 Exceptional! (323 reviews)
Perfect corner spot!
Reviewed on Sep 17, 2025
Chestnut Springs Hotel Deals
New Build! Log Cabin with Hot Tub in Wintergreen
Wintergreen Resort VA
10/10 Exceptional! (2 reviews)
Overall great experience. We did take down one smoke detector in down stairs bedroom due to beeping and I did not know where any batteries were. Other than that, everything was great!
Reviewed on Oct 17, 2025
4 BR cabin mins to trails & breweries pets welcome
Roseland VA
$522 nightly
The price is $586 total per night from Nov 30 to Dec 1
$586 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (28 reviews)
Nice place and very clean
Reviewed on Aug 22, 2025
Fully Loaded 8BR in Wintergreen! Sleeps 23
Wintergreen Resort VA
Our family had an excellent experience staying at this home during the fall. The host was extremely responsive, promptly addressing all of our questions and making sure we felt welcome. The house was exceptionally comfortable, spacious, and thoughtfully stocked with all the necessary utensils and ...
Reviewed on Nov 13, 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 Chestnut Springs
Reids Gap Trailhead
4.5/5(15 reviews)
You can take time to visit Reids Gap Trailhead during your travels to Roseland. Discover the mountain views in this relaxing area.
Woodson's Mill
You can spend an afternoon studying the exhibits at Woodson's Mill during your trip to Lowesville. Take in the museums while you're in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.