Chestnut Springs Vacations from $362
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The Latest Chestnut Springs Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Charlottesville
Hydraulic
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
8.2/10 Very Good! (570 reviews)
Elevator went out of service right after we moved into our 3rd floor room. Wasn’t too bad for us on the stairs but some other guests were struggling with their luggage when we left.
Reviewed on Jul 2, 2025
English Inn of Charlottesville
The Meadows
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (2,264 reviews)
It worked fine but was rough needed some TLC and clearly half ass cleaned. But it was the cheapest around that's for sure.....
Reviewed on Jul 9, 2025
Little Mod Hotel at the University
Venable
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (224 reviews)
The place has a great location, the staff was super friendly and helpful and the room was cute . Despite two window shades ( presumably one was room darkening) the outside light made our room much less dark than we would have preferred for sleeping .
Reviewed on Jul 10, 2025
Oakhurst Inn at the University
Jefferson Park Avenue
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (457 reviews)
This is a really cool property, i was visiting someone at the hospital (UVA) most of the time i didn't really get to enjoy the full property!
Reviewed on Jul 7, 2025
Chestnut Springs Hotel Deals
4 BR cabin mins to trails & breweries pets welcome
Roseland
$523 nightly
The price is $587 total per night from Jul 14 to Jul 15
$587 total
Jul 14 - Jul 15
Total includes taxes and fees
9.6/10 Exceptional! (24 reviews)
Outstanding property and communication
"Members of my family and I stayed at this property for a long weekend. The home is three levels which was awesome for those of us who wanted some down time to just chill. The main level being an open floor plan with a balcony was perfect for us all to enjoy each other’s company while reminiscing ..."
Reviewed on May 1, 2025
Sleep Inn Staunton
222 Jefferson Hwy, Staunton, VA
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $104 total per night from Aug 3 to Aug 4
$104 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (1,194 reviews)
"We recently stayed at this historic inn during an impromptu anniversary date and it was nothing short of magical. When we travel we love to find historic inns and this may be the most lovingly maintained in its original glory — every detail felt like a beautiful step back in time. The location is ..."
Reviewed on Jul 7, 2025
Hotel 24 South
24 South Market Street, Staunton, VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Aug 10 to Aug 11
$123 total
Aug 10 - Aug 11
Total includes taxes and fees
9.4/10 Exceptional! (1,009 reviews)
"We enjoyed the stay at the hotel. To enhance the experience the hotel may benefit from an update/renovation. :)"
Reviewed on Jul 6, 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.
Things to do
Shenandoah National Park Self-Guided Driving Audio Tour
$17
per traveler
100% of travellers recommend
Blue Ridge Parkway Self-Guided Audio Tour Bundle
$25
per traveler
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.