Howardsville, VA
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Holiday Inn Charlottesville-Monticello by IHG
1200 5th St. SW Charlottesville VA
Fully refundable
$97 nightly
The price is $111 total per night from Aug 31 to Sep 1
$111 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Sleep Inn & Suites Monticello
1185 5th St SW Charlottesville VA
$85 nightly
The price is $97 total per night from Aug 23 to Aug 24
$97 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Charlottesville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
8.4/10 Very Good! (1,008 reviews)
"I liked it here I s"
Reviewed on Aug 9, 2026
The Crossroads Inn
5010 Plank Rd North Garden VA
$205 nightly
The price is $235 total per night from Aug 17 to Aug 18
$235 total
Aug 17 - Aug 18
Total with taxes and fees
Book a stay at this luxury B&B in North Garden. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pippin Hill Farm & Vineyards and Albemarle ...
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.
Endless Mountain Top Views from All The Way Up!
Wintergreen Resort VA
Stay at this condo in Wintergreen. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Wintergreen Resort and Raven's Roost ...
10/10 Exceptional! (117 reviews)
"Great location with amazing views, perfect size living space, and everything we needed. Easy access to walking, hicking, swimming, golf, spa, food, etc. Short drive to wineries, recreational lake and local restaurants. Really didn't have to leave the mountain for much. Super enjoyable ..."
Reviewed on Jul 24, 2026
Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler VA
Stay at this cabin in Schuyler. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Walton's Mountain Museum and Caromont Farm are located ...
10/10 Exceptional! (196 reviews)
"This is a perfect cabin for a couple’s getaway. Our favorite part was sitting on the back deck in the evenings with the Mountain View and enjoying the stillness and song of nature. The cabin is very comfortable and has everything you need!"
Reviewed on Aug 5, 2026
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Roseland VA
Stay at this condo in Wintergreen. Enjoy free WiFi, laundry facilities, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Wintergreen ...
10/10 Exceptional! (368 reviews)
"Beautiful condo close to the Mountain Inn. Kitchen is well stocked and the owners provide a lot for your furry companions. We had a great time hiking the trails and coming back for a quiet evening. Wonderful place to stay and I can't wait to come back!!"
Reviewed on Aug 2, 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.
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- Flights from Boston (BOS) to Charlottesville (CHO)
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- Visit Schuyler
- Visit Wayland Park
- Visit Massies Mill
- Visit Arrington
- Caromont Farm
- Visit Covesville
- Visit Ivy
- Visit Crozet
- Visit Wingina
- Visit North Garden
- Visit Buckingham
- Visit Nellysford
- Visit Lake Monticello
- Visit Cumberland
- Visit Keswick
- Visit Scottsville
- Walton's Mountain Museum
- Visit Roseland
- Visit Piney Mountain
- Visit Wintergreen
- Visit Greenwood
- Visit Arvonia
- Visit Afton
- Visit Faber
- Visit Lowesville
- Visit Appomattox
- Visit Dillwyn
- Visit Charlottesville
- Visit Lovingston
- Visit Tyro
- Visit Palmyra
- Visit Lyndhurst
- Wintergreen Resort
- Trump Winery
- Carter Mountain Orchard
- James River
- George Washington National Forest
- Walton's Mountain Museum
- Bold Rock Hard Cider Nellysford Cidery
- Pippin Hill Farm & Vineyards
- Holliday Lake State Park
- Jefferson Vineyards
- Lovingston Winery
- Oak Ridge Estate
- Silverback Distillery
- Hill Top Berry Farm & Winery
- Blenheim Vineyards
- Bear Creek Lake State Park
- Virginia Blue Ridge Railway Trail
- Cardinal Point Vineyard and Winery
- Stoney Creek Golf Course
- Appomattox River
- Flying Fox Vineyard
- Winton Country Club
- Pine Knot
- James River Brewing
- DelFosse Vineyards and Winery
