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

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

9.6 out of 10, Exceptional, (297)
"Our girls getaway was perfect! The house was just as described and very clean!!! I’m a stickler for clean and every nook and cranny was spotless. There was only one tiny inconvenience with the hot hub not being filled quite enough and maybe not cleaned before we came because of a film on the surface. But the owner/host responded immediately. We had everything we needed to fix the issue. The house is in a perfect location and located on a cul de sac, so very private. Would highly recommend and we...
The price is AED 657
AED 1,534 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Family-friendly single home/Walking distance to shopping center and restaurants

9.6 out of 10, Exceptional, (23)
"This property was very clean, conveniently located and perfectly suited our needs. We would definitely stay here again!"
Family-friendly single home/Walking distance to shopping center and restaurants

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 AED 657
AED 1,518 total
includes taxes & fees
24 Mar - 25 Mar
Hillside Haven: Modern Retreat, Mountain Views

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

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 AED 496
AED 882 total
includes taxes & fees
26 Mar - 27 Mar
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (132)
"My family and I stayed here for a long weekend to make the most of some local hikes, end of season snow on the slopes and quality time together. The property met all of our needs and wants when we were browsing for availabilities. We had a hiccup accessing the property during initial check in (key code) but the property owners were helpful and got us in quickly. Their responsiveness eased my concerns right from the start, should we have needed them for anything else during our stay.What stood...
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

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

Charming Updated 3 Bedroom Home Near Downtown

9.8 out of 10, Exceptional, (50)
"We had a wonderful time staying at the house! Everything was clean and organized and our kids loved the yard. It is so close to downtown and we enjoyed going on family walks through the neighborhood. Would recommend to anyone!"
The price is AED 826
AED 1,730 total
includes taxes & fees
23 Mar - 24 Mar
Charming Updated 3 Bedroom Home Near Downtown

Spacious + Serene Mtn Top Escape, 4 En Suites

10.0 out of 10, Exceptional, (34)
"Hosts were great getting everything set for a last minute trip before a big snow storm. Very clean property; looks exactly as described in photos. 2-3 min drive from the base of the mountain."
The price is AED 611
AED 1,701 total
includes taxes & fees
25 Mar - 26 Mar
Spacious + Serene Mtn Top Escape, 4 En Suites

Boutique MicroHotel Room on Downtown Mall: The Townsman: Poe Room

10.0 out of 10, Exceptional, (2)
"This was perfect for our long weekend in Charlottesville. We enjoyed Monticello and various wineries. Had a wonderful meal at Public Fish and Oyster. Also visit Crush Pad, nearly across the street from the room. "
The price is AED 404
AED 570 total
includes taxes & fees
1 Apr - 2 Apr
Boutique MicroHotel Room on Downtown Mall: The Townsman: Poe Room

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

10.0 out of 10, Exceptional, (289)
"This annual family trip was even better than we imagined! We would return in a flash no matter the time of year. The house, resort, and surrounding areas have so much to offer and everyone in our family, of all ages, had a blast. The house was definitely bespoke, the kitchen well-supplied, and all rooms were beautiful and comfortable. Nephew and niece were especially impressed with the basement offerings. Winter Storm Kingston caused some emergency panic about accessibility and snow removal, but...
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

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!!!

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....

Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski

9.8 out of 10, Exceptional, (20)
"The house was nice and perfect for our group of three families with small children. Ideally, there would have been some basics in the house like oil and coffee filters. The garbage situation is a bit tricky as you have to take stuff to the dump yourself. Not a huge deal as the dump is on the way to wintergreen. But the dump is closed on Monday, which can present a problem if your check out is on Monday."
Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski

Book for Spring! Nelson 151, MTN views!

10.0 out of 10, Exceptional, (14)
"We had such a nice relaxing vacation. The views were beautiful. Great resource provided for local activities, trails, restaurants, etc."
Book for Spring! Nelson 151, MTN views!

Stuart Cottage: Walk to downtown + Sleeps 8

2.0 star property
10.0 out of 10, Exceptional, (6)
"I originally booked Stuart Cottage as I was looking for a place in Staunton while I was dealing with a serious family emergency. I am so lucky to have found this place on VRBO. Check-in process was a breeze, the property was immaculately clean, fully equipped kitchen with everything one could want (although I didn't have the opportunity to use it much - other than the coffee maker), nice sized bedrooms and baths, great washer/dryer, and excellent location in walking distance to Downtown. ...
The price is AED 635
AED 1,633 total
includes taxes & fees
24 Mar - 25 Mar
Stuart Cottage: Walk to downtown + Sleeps 8

Westerly Haven B: Walk to Scott Stadium!

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had four adults for a weekend getaway. The property is clean and well stocked. It is right off of I64 and within 15 min of the university and Monticello. Communication with the manager was easy and prompt. Their website is excellent with recommendations for food and activities. The only negative to this property is that it is not handicap accessible. The driveway is very steep and the stairs to the front door and upstairs are very steep. Otherwise, we thoroughly enjoyed our stay."
The price is AED 584
AED 1,411 total
includes taxes & fees
23 Mar - 24 Mar
Westerly Haven B: Walk to Scott Stadium!

Boutique Room steps from Downtown Mall | Rose Jean - Room #3

10.0 out of 10, Exceptional, (12)
"We had a lovely visit and found some wonderful places to eat!"
The price is AED 386
AED 746 total
includes taxes & fees
23 Mar - 24 Mar
Boutique Room steps from Downtown Mall | Rose Jean - Room #3

White Rock Cabin

10.0 out of 10, Exceptional, (202)
"Scott & Christie are excellent hosts. Everything was beyond expectations."
White Rock Cabin
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, (267)
"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 AED 386
AED 891 total
includes taxes & fees
23 Mar - 24 Mar
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (175)
"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 AED 394
AED 438 total
includes taxes & fees
30 Mar - 31 Mar
Valley Extended Suites

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (42)
"We booked this cottage strictly based off the aesthetic and rating. What a surprise when it turned out to be jsut the coziest, sleepiest little slice of whimsy! We were able to indulge in full relaxation and have the best girls trip. Thanks to the owner for creating such a beautiful space to make memories. "
The price is AED 731
AED 1,318 total
includes taxes & fees
31 Mar - 1 Apr
Ivy Rose Cottage nestled b/t Cville & Vineyards
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.