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Holiday Homes in Greenwood

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Greenwood

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
Situated in a charming brick building, The Loco 824 offers a unique storefront with a large glass window and a cozy outdoor seating area.

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

9.8 out of 10, Exceptional, (47)
"This was a perfect spot for exploring Charlottesville for a few days. Loved being so close to the downtown mall, an easy walk to explore shops and restaurants there, and also the great restaurants in the Belmont neighborhood. "
The price is AU$411
includes taxes & fees
12 Aug - 13 Aug
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
Farmhouse at the foot of the Blue Ridge Mountains
Relax on the deck with two comfortable rocking chairs, surrounded by a serene landscape.

Farmhouse at the foot of the Blue Ridge Mountains

10.0 out of 10, Exceptional, (24)
"This is a very comfortable, wonderfully quiet place. Excellent spot for a family. "
The price is AU$393
includes taxes & fees
18 Aug - 19 Aug
Farmhouse at the foot of the Blue Ridge Mountains
Secluded cabin on a horse farm, bordered by the North River
Enjoy meals in the kitchen with a central island and dining area, offering a view of the adjacent yard.

Secluded cabin on a horse farm, bordered by the North River

10.0 out of 10, Exceptional, (60)
"Great place to stay "
The price is AU$454
includes taxes & fees
10 Aug - 11 Aug
Secluded cabin on a horse farm, bordered by the North River
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Stroll through the beautifully maintained garden, featuring a variety of flowering plants and shrubs, along a shaded path.

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (243)
"Thanks for a wonderful stay at your beautiful farm! Great location for visiting wineries and Charlottesville."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Historic Beauty and Walkable to Everywhere
Relax with a meal or a drink in this outdoor seating area, surrounded by lush plants and flowers.

Historic Beauty and Walkable to Everywhere

10.0 out of 10, Exceptional, (50)
"We really enjoyed our stay here. The house was wonderful, very nicely decorated and clean. We really liked how close it was to all the unique restaurants and downtown.Nightlife"
The price is AU$619
includes taxes & fees
8 Aug - 9 Aug
Historic Beauty and Walkable to Everywhere
Upscale and Family-Friendly in Wintergreen
Relax in the hot tub surrounded by lush greenery and comfortable seating.

Upscale and Family-Friendly in Wintergreen

9.8 out of 10, Exceptional, (23)
"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"
Upscale and Family-Friendly in Wintergreen
The Firefly Springhouse
Access the upper level or storage area via the wooden staircase.

The Firefly Springhouse

10.0 out of 10, Exceptional, (30)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is AU$180
includes taxes & fees
12 Aug - 13 Aug
The Firefly Springhouse
Mountaintop Wintergreen Resort Home w/ Deck, Views
Enjoy a warm gathering space with a fireplace, flat-screen TV, and access to an outdoor deck.

Mountaintop Wintergreen Resort Home w/ Deck, Views

9.8 out of 10, Exceptional, (53)
"Second time staying here and we had the best time. Great for a weekend getaway to hang out with friends and family. "
Mountaintop Wintergreen Resort Home w/ Deck, Views
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
Enjoy a serene rural retreat with a spacious deck, pool, and hot tub overlooking rolling hills.

NEW! Secluded Farmhouse + Solar Heated Pool + Firepit

10.0 out of 10, Exceptional, (25)
"We had a great time. Very pretty house in a very pretty setting!"
NEW! Secluded Farmhouse + Solar Heated Pool + Firepit
White Rock Cabin
Enjoy meals at the central dining table in this well-lit kitchen.

White Rock Cabin

10.0 out of 10, Exceptional, (208)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin
Newtown Retreat: Award-Winning Renovation + Ideal Location
Enjoy cooking in this well-lit kitchen with an oven, gas stove, and large sink.

Newtown Retreat: Award-Winning Renovation + Ideal Location

10.0 out of 10, Exceptional, (27)
"This was a great place with a great location! 10/10 would stay here again."
Newtown Retreat: Award-Winning Renovation + Ideal Location
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Enjoy expansive views of the surrounding greenery from the large windows in this room, featuring a cozy seating area and a well-equipped kitchen.

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

10.0 out of 10, Exceptional, (295)
"The house was perfect for us. Plenty of space for everyone to hang out together. "
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop
Pryor-Haynes House | 4 Bed, 4.5 Bath
Enjoy cooking in this kitchen with a double sink, oven, and range hood.

Pryor-Haynes House | 4 Bed, 4.5 Bath

9.6 out of 10, Exceptional, (108)
"We had a friend reunion and stayed at the house. Everyone loved it! We love the decor! "
Pryor-Haynes House | 4 Bed, 4.5 Bath
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and sink.

The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!

10.0 out of 10, Exceptional, (19)
"Such a great property and the owners are great! The house is super close to everything and the neighborhood is great. We can’t wait to book again! "
The All-American Cottage Seconds from Gypsy Hill Park! Kid and Pet friendly!
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Relax in a spacious hot tub with four jets for a rejuvenating soak.

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (46)
"Check-in process was a breeze, communication with the hosts was super easy and consistent. Place was very clean and exactly as appears in the pictures. My group had an amazing time and loved the location of this property. Would 110% stay here again!"
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Montrose Manor- In the heart of Belmont!
Enjoy cooking and dining in this well-equipped kitchen with a central island, sink, and flat-screen TV.

Montrose Manor- In the heart of Belmont!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had an excellent experience at Montrose Manner. The location was walkable to the downtown mall & Belmont. We enjoyed exploring both & especially liked the restaurant scene in Belmont. Francesca was an outstanding host & quickly responded to our inquiries. The house is beautifully updated & well appointed. Our group highly recommends Montrose Manor!"
The price is AU$694
includes taxes & fees
11 Aug - 12 Aug
Montrose Manor- In the heart of Belmont!
Yellow House| 2 BR Cottage Dtwn Cville/Belmont
Enjoy the serene atmosphere from the deck with a view of lush green surroundings.

Yellow House| 2 BR Cottage Dtwn Cville/Belmont

10.0 out of 10, Exceptional, (58)
"This was a great location, wonderful for the kids. Everything was clean, comfortable, and welcoming. Easy for the family to stay and everything we needed. Will definitely stay again "
Yellow House| 2 BR Cottage Dtwn Cville/Belmont
Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!
Compact kitchen with microwave, stove, and countertop, adjacent to a doorway.

Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!

10.0 out of 10, Exceptional, (2)
"We traveled to VA from NY. Check in was easy and simple. As was checkout. It was conveniently located to a lot of places. Would stay again "
Charming 3-bedroom house, breweries! hiking! wineries! scenic routes! Fishing!
Cooler in the mountains, with hot tub.
Property grounds

Cooler in the mountains, with hot tub.

9.8 out of 10, Exceptional, (66)
"House was perfect for a weekend of skiing. You’re able to walk to the resort from the house which was a huge plus since it was a packed weekend. Overall great stay! "
Cooler in the mountains, with hot tub.
RiverFront Country Home with Blue Mountain Views
Relax in a serene outdoor setting with two comfortable chairs and a small table amidst lush greenery.

RiverFront Country Home with Blue Mountain Views

9.8 out of 10, Exceptional, (24)
"This property is adorable and is a clean and comfy stay! Owner was great to deal with."
RiverFront Country Home with Blue Mountain Views
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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