Howardsville, VA
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Holiday Inn Charlottesville-Monticello by IHG
1200 5th St. SW Charlottesville VA
Fully refundable
$89 nightly
The price is $102 total per night from Oct 25 to Oct 26
$102 total
Oct 25 - Oct 26
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
$82 nightly
The price is $93 total per night from Oct 18 to Oct 19
$93 total
Oct 18 - Oct 19
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 ...
The Crossroads Inn
5010 Plank Rd North Garden VA
$205 nightly
The price is $235 total per night from Sep 28 to Sep 29
$235 total
Sep 28 - Sep 29
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 ...
9.8/10 Exceptional! (69 reviews)
"Five stars! With a property circa 1830 (so much charm), I didn’t expect such a quiet luxe experience—great bed, pillows, and linens, soft robes, perfect in-room coffee service, convenient for plugging in all your modern technology, well thought-out lighting, very tasteful decor (in keeping with the ..."
Reviewed on Sep 26, 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.
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! (374 reviews)
"Wonderful condo in a good location with pretty easy walking access to the main lodge and market store. We really enjoyed this property."
Reviewed on Sep 2, 2026
Peacefull, private Cabin! 140 acres,mile of river trails! 10 minutes to Rt.151!
Faber VA
Stay at this cabin in Faber. Enjoy free WiFi, a garden, and patios. Popular attractions DelFosse Vineyards and Winery and Hill Top Berry Farm & Winery are located ...
10/10 Exceptional! (66 reviews)
"Perfect quiet solitude is what we hoped for and received it beyond measure. The bed was the most comfortable sleeping experience I’ve had in years. As someone with severe back issues I always worry when we book a vacation. I didn’t need to worry at all. I haven’t slept this much in years. The icing ..."
Reviewed on Aug 18, 2026
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland VA
Stay at this condo in Wintergreen. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Wintergreen Resort and Raven's Roost Overlook ...
9.6/10 Exceptional! (161 reviews)
"This place was spotless and cozy we loved it!"
Reviewed on Sep 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.
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- 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
- Oak Ridge Estate
- Jefferson Vineyards
- Lovingston Winery
- Blenheim Vineyards
- Silverback Distillery
- Holliday Lake State Park
- Bear Creek Lake State Park
- Stoney Creek Golf Course
- Hill Top Berry Farm & Winery
- Appomattox River
- James River Brewing
- Winton Country Club
- Layz S Ranch
- Cardinal Point Vineyard and Winery
- DelFosse Vineyards and Winery
- Virginia Blue Ridge Railway Trail
- Buckingham Historic Village
