Photo by Karyn Leary

Holiday Homes in Greenwood

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in Greenwood

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

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

9.6 out of 10, Exceptional, (293)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Property grounds

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

10.0 out of 10, Exceptional, (49)
"We just left this morning, and we are already planning our next stay. This place was absolutely PERFECT. It had every amenity we could ever need, especially the kitchen. The hot tub was exactly what we "
The price is AU$1,135
includes taxes & fees
2 Mar - 3 Mar
Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Interior

Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort

10.0 out of 10, Exceptional, (63)
"The house is perfect and only 10 minutes from the slopes."
Relaxing 3 bdrm Mountain Cabin on Wintergreen Resort
Wintergreen Resort Post & Beam Home Beauty
Smart TV, fireplace, offices

Wintergreen Resort Post & Beam Home Beauty

9.8 out of 10, Exceptional, (16)
"Everything about the listing and the location was spot on. We have stayed in numerous VRBO-units all over, and this was one of the most well-stocked homes I’ve seen. The house was very convenient to Wintergreen for fun winter activities, and the three bedrooms bathrooms were perfect for our family of 5. The kids loved the little loft space for playing card games, and we loved the view from the main living room. The only thing I’d suggest to the owner would be a handy-man to tighten the...
Wintergreen Resort Post & Beam Home Beauty
Hilltop Escape At Wintergreen
Smart TV, fireplace

Hilltop Escape At Wintergreen

2.0 star property
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our time in the house! We loved the family room and fireplace. The kitchen was also very well stocked. We appreciated so much all the extra amenities of soap, shampoo and body wash. As well as firewood for the fireplace. The hot tub was broken… but the property manager was exceptional! He tried his best to get it up and running but was unsuccessful. He was very responsive and kind. "
Hilltop Escape At Wintergreen
Historic Beauty and Walkable to Everywhere
Outdoor dining

Historic Beauty and Walkable to Everywhere

10.0 out of 10, Exceptional, (39)
"A clean and charming stay a short walk from downtown. Really enjoyed our stay."
The price is AU$355
includes taxes & fees
24 Feb - 25 Feb
Historic Beauty and Walkable to Everywhere
Boutique Room steps from Downtown Mall | Rose Jean - Room #3
Outdoor dining

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

10.0 out of 10, Exceptional, (11)
"The check-in process was super easy, all automated. You do have to pay for parking but we used the garage which was a block away and it was 12 for the day. The place was very modern and clean. The location was great, about a block off the pedestrian mall. There are 3 restaurants right next to the house, if you needed a quick bite, It was quiet during our stay and we had a great experience. I would defy stay here again! "
The price is AU$326
includes taxes & fees
24 Feb - 25 Feb
Boutique Room steps from Downtown Mall | Rose Jean - Room #3
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (81)
"Beautiful area and beautiful home."
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
Charming Updated 3 Bedroom Home Near Downtown
Fridge, microwave, oven, stovetop

Charming Updated 3 Bedroom Home Near Downtown

9.8 out of 10, Exceptional, (49)
"Super accommodating host and very nice property— clean and comfortable. "
The price is AU$744
includes taxes & fees
25 Feb - 26 Feb
Charming Updated 3 Bedroom Home Near Downtown
The Navel Nalle: Downtown Bungalow, Patio, Parking
Fridge, microwave, oven, stovetop

The Navel Nalle: Downtown Bungalow, Patio, Parking

10.0 out of 10, Exceptional, (4)
"Stayed for a quick trip to go to a UVA basketball game. Host was very responsive leading up to the stay. House was well appointed, clean and very accommodating. Host was responsive throughout the duration with any questions. Would definitely recommend!"
The price is AU$1,032
includes taxes & fees
24 Feb - 25 Feb
The Navel Nalle: Downtown Bungalow, Patio, Parking
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Fridge, microwave, oven, stovetop

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (173)
"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!
Cooler in the mountains, with hot tub.
Outdoor pool

Cooler in the mountains, with hot tub.

9.8 out of 10, Exceptional, (65)
"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.
Red White & WTG: Game Room + Hot Tub
Exterior

Red White & WTG: Game Room + Hot Tub

The price is AU$1,518
includes taxes & fees
25 Feb - 26 Feb
Red White & WTG: Game Room + Hot Tub
4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku
Terrace/patio

4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

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!!!
Secluded winter getaway, Nelson 151, MTN views!
Fridge, microwave, oven, stovetop

Secluded winter getaway, Nelson 151, MTN views!

10.0 out of 10, Exceptional, (13)
"We loved our stay! House was lovely and views were amazing. Very peaceful! We really enjoyed the fireplace since the weather was bad. It was close to wineries, distilleries and restaurants. Katie, our host, was so responsive from booking to departing. You get a Guide Book which is so helpful. We would definitely return. Loved it! "
Secluded winter getaway, Nelson 151, MTN views!
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes
Fridge, microwave, oven, stovetop

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (55)
"This was the prefect house for the holiday. Plenty of space for our family yet very cozy. The temps were cold and we had the fire place going every night. The views from the main room and master suite were breathtaking. The owners were very responsive and communicative. Highly recommend this home to anyone wanting a mountain getaway to Wintergreen resort!"
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes
White Rock Cabin
Property grounds

White Rock Cabin

10.0 out of 10, Exceptional, (199)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin
Cozy Craftsman: Newly Renovated/Downtown Staunton
Exterior

Cozy Craftsman: Newly Renovated/Downtown Staunton

9.6 out of 10, Exceptional, (15)
"We had a wonderful stay at the Cozy Craftsman! The home is beautiful and clean, great kitchen, two full bathrooms, and lots of space. It is super close to downtown (15 minute walk or a few minutes drive). We would definitely stay here again and would recommend to everyone!"
The price is AU$552
includes taxes & fees
23 Feb - 24 Feb
Cozy Craftsman: Newly Renovated/Downtown Staunton
RiverFront Country Home with Blue Mountain Views
Pet-friendly

RiverFront Country Home with Blue Mountain Views

9.8 out of 10, Exceptional, (24)
"Plenty of space for everyone. Grandchildren loved the playground and the big yard. "
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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Other property types in Greenwood

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

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

9.0 out of 10, Wonderful, (265)
"Overall our stay was great, the place had a great view and was super clean, the property managers were easy to reach as well! Two things to note i would suggest bringing a throw blanket if you get cold easily as there were no extras, also the hot tub mentioned in the comments is actually just the master bed rooms tub! "
The price is AU$385
includes taxes & fees
24 Feb - 25 Feb
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Valley Extended Suites
Standard Suite | Private kitchen

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (173)
"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 AU$186
includes taxes & fees
24 Mar - 25 Mar
Valley Extended Suites
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Terrace/patio

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

9.6 out of 10, Exceptional, (293)
"Cozy, Clean and Convenient!"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
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.