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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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Cottages in Zion Crossroads

1802 cottage once part of Monticello and owned by Thomas Jefferson
Stroll up the traditional staircase to a charming entrance surrounded by lush greenery and beautiful flowering plants.

1802 cottage once part of Monticello and owned by Thomas Jefferson

9.4 out of 10, Exceptional, (83)
"This is a great place to stay. Close to town but out on a large very private farm. Highly recommend. "
1802 cottage once part of Monticello and owned by Thomas Jefferson
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Situated in a wooded area, this cottage offers a serene and setting with a well-maintained lawn and mature trees.

Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries

9.0 out of 10, Wonderful, (116)
"The listing is very accurate and was clean. My entire family loved staying!"
$191 nightly
The price is $201
Aug 18 - Aug 19
Total includes taxes and fees
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK
Situated in a serene natural setting, this charming property features a porch with a flagpole and a grassy lawn.

Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK

10.0 out of 10, Exceptional, (35)
"This is the third time we have stayed and are never disappointed. If you are visiting friends or family in Lake Monticello, this is a perfect spot."
Bluebird Cottage A: Near Charlottesville, Wineries: Firepit, Patio, Dogs OK
Cowboy hide-a-way cottage with hot tub on historic farm close to everything
Relax in a serene hot tub under a shaded pergola with a view of the surrounding green landscape.

Cowboy hide-a-way cottage with hot tub on historic farm close to everything

9.4 out of 10, Exceptional, (25)
"Beautiful property the cabin is so cute perfectly situated the hot tub is awesome very clean just a beautiful getaway and not a far drive highly highly recommend"
Cowboy hide-a-way cottage with hot tub on historic farm close to everything
Elegant Cottage on 600 Acre Horse & Livestock Farm
Relax in a serene outdoor space with a round table, wicker chairs, and a cushioned bench, surrounded by a fenced pasture view.

Elegant Cottage on 600 Acre Horse & Livestock Farm

9.8 out of 10, Exceptional, (143)
"It’s Very secluded , the horses next to the house are adorable, perfect place with kids..We really enjoyed . "
$271 nightly
The price is $291
Aug 11 - Aug 12
Total includes taxes and fees
Elegant Cottage on 600 Acre Horse & Livestock Farm
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.
Stonemont Farm Cottage in Keswick near Vineyards!
Cozy cottage with a welcoming entrance, surrounded by lush greenery and a well-maintained lawn.

Stonemont Farm Cottage in Keswick near Vineyards!

9.8 out of 10, Exceptional, (22)
"We chose to visit the Charlottesville area for spring break. The cottage was lovely and had everything we needed for our stay. Every room in the house was comfortable and nicely decorated. It was a short drive to Monticello, downtown, and the wineries. The pond was a bonus…my kids were pumped when they caught a few fish. Thank you for sharing your home. "
Stonemont Farm Cottage in Keswick near Vineyards!
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

9.6 out of 10, Exceptional, (7)
"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
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Relax in a serene garden setting with a comfortable seating area featuring two chairs and lush greenery.

Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

10.0 out of 10, Exceptional, (36)
"Such a great place for a wine weekend trip that isn’t right in the middle of UVA but just a 15 min drive to downtown. The chickens were for sure the stars, would def come back! "
$168 nightly
The price is $192
Aug 13 - Aug 14
Total includes taxes and fees
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy
Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries
Situated in a peaceful natural setting, this charming building features a porch with a red accent and an American flag.

Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries

10.0 out of 10, Exceptional, (42)
"This was a great stay! There are very nice touches in the place and the snacks were appreciated. It is spotless with everything needed for a comfortable time, The beds are great we loved the fire pit. Will stay again! "
Bluebird Cottage B: Firepit, Patio, Games; Near Charlottesville, Wineries
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
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
A rustic barn stands amidst a lush green landscape.

Servants' Cottage on 600 Acre Working Horse/Cattle Estate

9.8 out of 10, Exceptional, (136)
"Property was very peaceful. Very much enjoyed the stay. Everyone was very friendly. "
$185 nightly
The price is $199
Aug 11 - Aug 12
Total includes taxes and fees
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Escape to a serene cabin surrounded by a lush lawn and a beautiful flowering tree.

'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.

9.8 out of 10, Exceptional, (84)
"Fifth year at Wolftrap Farm. Booked again for 2025.Thanks!"
$283 nightly
The price is $304
Aug 18 - Aug 19
Total includes taxes and fees
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
Charming Cottage on beautiful Farm & Vineyard
Relax on the deck with a potted plant and comfortable seating for four.

Charming Cottage on beautiful Farm & Vineyard

10.0 out of 10, Exceptional, (30)
"Great stay, great place!"
Charming Cottage on beautiful Farm & Vineyard
Cozy Log Cabin Getaway w/ Fire Pit + 3 Acres!
Relax on the porch with a swing chair and bench, surrounded by lush greenery and a stone wall.

Cozy Log Cabin Getaway w/ Fire Pit + 3 Acres!

3.0 star property
Cozy Log Cabin Getaway w/ Fire Pit + 3 Acres!
Charming Eastham Guesthouse
Terrace/patio

Charming Eastham Guesthouse

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cute place! Exactly as pictured. We loved our stay! Beautiful location! Take a picture of the key code to get in the door as cell service is spotty. "
$191 nightly
The price is $218
Aug 11 - Aug 12
Total includes taxes and fees
Charming Eastham Guesthouse
Historic Farmhouse w/ Chef's Kitchen Near Wineries
Relax on the covered porch with a view of the beautifully landscaped garden.

Historic Farmhouse w/ Chef's Kitchen Near Wineries

3.0 star property
Historic Farmhouse w/ Chef's Kitchen Near Wineries
Charming Charlottesville Apt w/ Outdoor Space!
House (1 Bedroom) | Interior

Charming Charlottesville Apt w/ Outdoor Space!

3.0 star property
Charming Charlottesville Apt w/ Outdoor Space!
Locust Garden, A North Downtown C'ville Guesthouse
Relax on the porch with a view of lush gardens.

Locust Garden, A North Downtown C'ville Guesthouse

2.0 star property
8.0 out of 10, Very Good, (1)
"Very clean and sweet property. Attractively furnished. Check in was easy. Good communication.Kitchen was very easy to use. Did lots of our own cooking. Would have appreciated some quality stainless steel pots and tops as we can’t use anodized cookware for specific health reasons."
$273 nightly
The price is $313
Aug 26 - Aug 27
Total includes taxes and fees
Locust Garden, A North Downtown C'ville Guesthouse
Group Getaway ~ 15 Mi to Charlottesville!
Stunning two-story house with a central entrance and gabled roof, set amidst a beautifully manicured lawn.

Group Getaway ~ 15 Mi to Charlottesville!

3.0 star property
Group Getaway ~ 15 Mi to Charlottesville!
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 Zion Crossroads Hotel Reviews

Holiday Inn Charlottesville-Monticello by IHG

Holiday Inn Charlottesville-Monticello by IHG

10/10 Excellent
"The food was very good. Much better than I expected."
MO 1-night trip
Posted 19 hours ago
Holiday Inn Charlottesville-Monticello by IHG