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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Howardsville Cottages

Mechum Hill Cottage: Central to Crozet & Cville
Enjoy serene views of the forest from this outdoor space, perfect for dining or relaxation.

Mechum Hill Cottage: Central to Crozet & Cville

9.4 out of 10, Exceptional, (12)
"The location and very clean cottage"
The price is CA $177
CA $385 total
includes taxes & fees
Aug 10 - Aug 11
Mechum Hill Cottage: Central to Crozet & Cville
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Relax on the deck with a glass-enclosed space, two chairs, and a small table amidst lush greenery.

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

10.0 out of 10, Exceptional, (19)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
The price is CA $260
CA $634 total
includes taxes & fees
Aug 10 - Aug 11
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Quiet Blue Ridge Mountain Cottage
Relax on the porch with a swing seat suspended from the ceiling, surrounded by lush greenery and a serene atmosphere.

Quiet Blue Ridge Mountain Cottage

9.6 out of 10, Exceptional, (88)
"small, quaint little cottage that accommodated our lodging needs sufficiently"
Quiet Blue Ridge Mountain Cottage
Clear Sky Cottage - A Spacious 1 BR Cottage Close to Charlottesville & Wineries.
Exterior

Clear Sky Cottage - A Spacious 1 BR Cottage Close to Charlottesville & Wineries.

10.0 out of 10, Exceptional, (1)
"Beautifully decorated and super clean. They’ve thought of all the little touches. Location is perfect, around 7 miles outside of town but in the peaceful countryside. We sat on the porch watching wildlife in the back. There are vineyards and breweries in all directions. We visited Monticello and even mountain top orchards. Owners were great. We will be returning. "
Clear Sky Cottage - A Spacious 1 BR Cottage Close to Charlottesville & Wineries.
Brand new serene luxury cottage just off the Brew Ridge Trail
Exterior

Brand new serene luxury cottage just off the Brew Ridge Trail

The price is CA $106
CA $219 total
includes taxes & fees
Aug 18 - Aug 19
Brand new serene luxury cottage just off the Brew Ridge Trail
Loveshack, a charming tiny house on a 5 acre farm
Guests enter through a charming stone pathway to a single-story building with a gabled roof.

Loveshack, a charming tiny house on a 5 acre farm

9.4 out of 10, Exceptional, (6)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
Enjoy al fresco dining on the deck with a round table and grill.

Afton Cottage w/ Hot Tub, Firepit, Mountain Views

9.8 out of 10, Exceptional, (8)
"Very quiet and peaceful. Perfect for a couples getaway :) "
The price is CA $188
CA $443 total
includes taxes & fees
Aug 10 - Aug 11
Afton Cottage w/ Hot Tub, Firepit, Mountain Views
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Stunning two-story house with a central entrance and symmetrical facade.

❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!

9.8 out of 10, Exceptional, (25)
"We had a great time!! The house was spotless, hot tub was great, and the fire pit was perfect! We had fun playing pool every night and seeing the animals next door during the day. Master bedroom and bathroom are amazing!!!"
The price is CA $235
CA $889 total
includes taxes & fees
Aug 12 - Aug 13
❤️️Stoney Creek Cottage❤️️Minutes to Wintergreen!
Serene Roseland Retreat Near Wintergreen Resort!
House (3 Bedrooms) | Interior

Serene Roseland Retreat Near Wintergreen Resort!

3.0 star property
Serene Roseland Retreat Near Wintergreen Resort!
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Set amidst lush greenery, this two-story house offers a serene retreat with a balcony overlooking the surrounding landscape.

Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries

10.0 out of 10, Exceptional, (25)
"My husband and I enjoyed this home so much! Beautiful location, house is immaculate, communication with owners was perfect! Cannot say enough wonderful things. We booked it again immediately for a trip we having coming in the fall. "
Fairwood Cottage-Exceptional 1BR Cottage Minutes From Charlottesville & Wineries
Bluebird Cottage: Near 151 + Appalachian Trail
Relax in this serene outdoor space with a glass-enclosed view of the lush lawn and trees.

Bluebird Cottage: Near 151 + Appalachian Trail

2.0 star property
7.8 out of 10, Good, (7)
"Such a cute house! Had a very relaxing time! Great location to one of our favorite spots - Bold Rock! "
The price is CA $158
CA $401 total
includes taxes & fees
Aug 17 - Aug 18
Bluebird Cottage: Near 151 + Appalachian Trail
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Situated in a rural setting, this house offers a covered outdoor seating area with a table and chairs.

Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!

10.0 out of 10, Exceptional, (13)
"We really enjoyed our stay. The house, as always, is well stocked and clean. Very convenient location."
Hot Tub! Short walk to Three Notch'd - Charming Mid-Century Modern Cottage!
Beautiful, Remodeled Cottage in the Heart of Afton
Set amidst a lush garden, this charming house features a cozy porch and a well-manicured yard with a gravel path.

Beautiful, Remodeled Cottage in the Heart of Afton

10.0 out of 10, Exceptional, (65)
"My husband and I were just looking for a quick getaway for the weekend and this was perfect!"
Beautiful, Remodeled Cottage in the Heart of Afton
Cozy cottage with PRIVATE hot tub and year round pool.
Stroll through the serene surroundings of this two-story home, featuring a charming porch and a detached garage.

Cozy cottage with PRIVATE hot tub and year round pool.

10.0 out of 10, Exceptional, (3)
"Host was available and helpful. Property is clean and comfortable. Traffic noise was a lot louder than expected but overall a great stay!"
Cozy cottage with PRIVATE hot tub and year round pool.
Cottage w/ James River Access in Wingina!
Relax on the porch with two comfortable rocking chairs, each with a cushion featuring the word 'Lives Here'.

Cottage w/ James River Access in Wingina!

3.0 star property
Cottage w/ James River Access in Wingina!
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Enjoy the serene forest view from this cozy porch with a hanging plant arrangement and large windows.

Wintergreen Resort Home w/ 2 Decks + Ski Access!

3.0 star property
Wintergreen Resort Home w/ 2 Decks + Ski Access!
Grand Chalet w/ Hot Tub - Near Wintergreen Resort
Relax in a hot tub on a raised deck with a view of the surrounding trees and sky.

Grand Chalet w/ Hot Tub - Near Wintergreen Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"The Shamokin Chalet (Grand Chalet) was a gorgeous home with amazing mountain views! It was one of the most well appointed homes I’ve stayed in - well stocked kitchen (paper products, spices, dishes, cooking supplies, coffees), shampoos, conditioners, body wash, toilet paper and plenty of towels in all bathrooms, even beach towels for the hot tub. The home was beautifully decorated and immaculate. The landscaping was gorgeous. It had the most massive TV I’ve ever seen. The owner was a great...
Grand Chalet w/ Hot Tub - Near Wintergreen Resort
Blue Rivers Cottage with Mountain Views
Enjoy outdoor dining or relaxation on the deck with a round table and two chairs, surrounded by lush greenery.

Blue Rivers Cottage with Mountain Views

10.0 out of 10, Exceptional, (3)
"This property is beautiful inside and out, and we were very comfortable during our stay. Highly recommend!!"
Blue Rivers Cottage with Mountain Views
Cozy 'hillside Hideaway' in Wintergreen Resort!
Guests can enjoy a rustic cabin-style retreat with a spacious deck and easy access to multiple levels.

Cozy 'hillside Hideaway' in Wintergreen Resort!

3.0 star property
Cozy 'hillside Hideaway' in Wintergreen Resort!
Spacious Home: 10 Miles to Wintergreen Resort!
House (3 Bedrooms) | Interior

Spacious Home: 10 Miles to Wintergreen Resort!

3.0 star property
Spacious Home: 10 Miles to Wintergreen Resort!
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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Top Howardsville Hotel Reviews

Sleep Inn & Suites Monticello

Sleep Inn & Suites Monticello

10/10 Excellent
"There was no air in the elevator or hallways. Otherwise a very nice hotel."
James 4-night trip
Posted 3 days ago
Sleep Inn & Suites Monticello