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Compare 550 Vacation Homes in Greenwood with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (236)
"The farm experience was delightful for the children, ages 7, 5, 3, and 1."
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Historic Beauty and Walkable to Everywhere

10.0 out of 10, Exceptional, (41)
"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 SAR 529
SAR 1,055 total
includes taxes & fees
31 Mar - 1 Apr
Historic Beauty and Walkable to Everywhere

Wintergreen Resort Post & Beam Home Beauty

9.8 out of 10, Exceptional, (18)
"Terrific, well appointed, every thing we needed. "
Wintergreen Resort Post & Beam Home Beauty

The Landmark: Luxury In Downtown Staunton

10.0 out of 10, Exceptional, (17)
"Great place for a group stay. Everything you need to cook if you wish. Street is a bit busy, parking limited to 2 vehicles."
The Landmark: Luxury In Downtown Staunton

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (298)
"The house is so nice, and area is gorgeous. We do an annual girls trip, and this was perfect for us. Walking distance to a store was nice as well. The owners were only a text away if we needed anything, but we didn't. Highlyrecommend. "
The price is SAR 672
SAR 1,584 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

10.0 out of 10, Exceptional, (52)
"If you like animals this is the place to be. The views is beautiful. Not to mention the house was lovely."
The price is SAR 563
SAR 1,159 total
includes taxes & fees
28 Mar - 29 Mar
Secluded cabin on a horse farm, bordered by the North River

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

9.8 out of 10, Exceptional, (40)
"Cute and convenient to Downtown Mall and Belmont. Beds were comfortable and communication with the host could not have been easier. Highly recommend!! "
The price is SAR 506
SAR 888 total
includes taxes & fees
9 Apr - 10 Apr
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

9.0 out of 10, Wonderful, (2)
"The property is about a 5-7 minute drive to the Wintergreen resort. It was an excellent choice for multiple families who have kids. The downstairs area is full of entertaining games such as foosball, basketball, and darts. It also includes arcade games and multiple TVs. This area kept all the kids entertained whenever the adults were upstairs. "
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

9.8 out of 10, Exceptional, (149)
"This was our second time staying at Sarah's cottage downtown. It's super convenient for our family of four and small dog when we're in town to visit family."
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive

Yellow House| 2 BR Cottage Dtwn Cville/Belmont

10.0 out of 10, Exceptional, (47)
"Great location and very comfortable accommodations. We explored Charlottesville and the Wineries during the day and were able to walk to breakfast and dinner every day for fantastic meals. Can’t wait to return!!"
Yellow House| 2 BR Cottage Dtwn Cville/Belmont

GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!

9.6 out of 10, Exceptional, (8)
"This was the best house to relax and unwind with a group of friends! We immediately fell in love with the coziness of the house. The location is great and was easy to get to. Would 10/10 recommend! "
GreenLeaf |3 bed, 2 Bath in Rugby Hills - Great central location UVA and Downtown Cville!

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

10.0 out of 10, Exceptional, (11)
"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!

Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger

10.0 out of 10, Exceptional, (14)
"Excellent decor. Very comfortable bed. Would stay again."
Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger

Walkable to UVA, and Fontaine Research park, Newly Renovated Home.

7.8 out of 10, Good, (20)
"Great location for our family visit for holiday…access was simple and straightforward. Single bathroom was tight but manageable. There were several areas that needed deep cleaning including window ledges, baseboards and blinds which had caked dirt and bugs"
Walkable to UVA, and Fontaine Research park, Newly Renovated Home.

NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

10.0 out of 10, Exceptional, (23)
"Wonderful place to stay for a family reunion-kids loved the pool and frisbee golf. The owners even had pool toys for the kids to use! "
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (26)
"Imagine a house for 7 adult couples to relax, drink and be merry without feeling cramped. This house was absolutely astonishing. Each couple had a room with bathroom. The decor and upgrades, in every single room, offers inspiration and is 1,000% upscale.The great room view is breathtaking and the home is in close proximity to the slopes.This was my first time using VRBO and the owner was very responsive to all messages throughout the process. He has set the bar high.We will visit again!"
Insane Mountain Views - New Listing

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

10.0 out of 10, Exceptional, (42)
"Everything was as advertised- family of 6 was well accommodated for a Thanksgiving weekend. Very cold windy and snowy outside but house was warm and comfortable. Very large kitchen was well suited for preparing Thanksgiving dinner. "
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Afton Farmhouse - Mountain Views off Route 151

10.0 out of 10, Exceptional, (16)
"The house was really cozy with lots of space inside and outside to enjoy. We enjoyed playing games, sitting by the fire inside and outside, and visiting the local wineries and breweries. Ashley was an excellent host and quick to respond with any questions. "
The price is SAR 626
SAR 1,736 total
includes taxes & fees
31 Mar - 1 Apr
Afton Farmhouse - Mountain Views off Route 151

Hillside Haven: Modern Retreat, Mountain Views

10.0 out of 10, Exceptional, (23)
"The place was exactly as advertised. We had a great experience. Host was super responsive, would absolutely stay there again. "
The price is SAR 672
SAR 1,559 total
includes taxes & fees
1 Apr - 2 Apr
Hillside Haven: Modern Retreat, Mountain Views

Come and enjoy a beautiful view and relaxing time at Windy Knoll....

10.0 out of 10, Exceptional, (197)
"This was a perfect place for our bestie gathering. The location is beautiful...secluded and lovely. The house was truly impeccable. We loved the space. It was so well appointed with the little things that you may need. Simply awesome! Thank you to these great hosts!thoughtfully!"
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
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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Other property types in Greenwood

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (268)
"The date of my stay was Sun Feb 9 - Tues Feb 11, 2025. It was a great place to stay with beautiful views. Our stay was short. We were there for my son to participate in WASI- Wintergreen Alpine Special Invitational. Travel to the Mountain Inn for ski competition and celebration was easy. I really enjoyed having the full kitchen so we could make breakfast each day. The washer and dryer were helpful for keeping ski bibs clean and dry."
The price is SAR 394
SAR 889 total
includes taxes & fees
16 Apr - 17 Apr
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (176)
"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"
The price is SAR 398
SAR 443 total
includes taxes & fees
13 Apr - 14 Apr
Valley Extended Suites

Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi

10.0 out of 10, Exceptional, (36)
"This was the perfect stay for what we needed (and more). I packed a ton of books and toys for our kids, but they didn't touch a single one. The house had a bin of toys, a bunch of games (we played candyland), stuffed animals in every room, and even a workout room we did a fun family workout in! The weather was just cold enough that we decided against s'mores, but we hung out by the water and promised the kids we'll be back when it's warmer.We also brought our dog, who we may not bring next time....
The price is SAR 540
SAR 906 total
includes taxes & fees
31 Mar - 1 Apr
Magical Log Cabin, streams in private yard, 4 bedrooms, pet friendly, WiFi
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.