Photo by Karyn Leary

Greenwood Holiday Rentals

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Check prices for these dates

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Holiday Rentals in Greenwood

Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Wintergreen
10.0 out of 10, Exceptional, (252)
"Stayed 3 nights for a wedding at Wintergreen. Wonderful place with spectacular views "
United States
Michael S.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Terrace/patio
Love Ridge Mountain Lodging

Love Ridge Mountain Lodging

3.0 star property
Montebello
10.0 out of 10, Exceptional, (13)
"Amazing stay I had, very peaceful and very quiet. "
United States
Abby
The price is HK$1,398
HK$2,038 total
includes taxes & fees
11 Dec - 12 Dec
Love Ridge Mountain Lodging
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Chestnut Springs
10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
The price is HK$4,087
HK$7,938 total
includes taxes & fees
7 Jan - 8 Jan 2026
New Build! Log Cabin with Hot Tub in Wintergreen
Exterior
Wow! What A View!

Wow! What A View!

Wintergreen Resort
10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

Roseland
9.0 out of 10, Wonderful, (302)
"Great view!!"
United States
Suzanne W.
The price is HK$694
HK$1,741 total
includes taxes & fees
9 Dec - 10 Dec
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Outdoor dining
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Wintergreen Resort
9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Roseland
10.0 out of 10, Exceptional, (336)
"Great stay, highly recommended"
United States
Jeffrey E.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Property grounds
Large and Luxurious Exec 5BR Chalet

Large and Luxurious Exec 5BR Chalet

Pedlars Edge
10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet
Pool
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is HK$856
HK$1,950 total
includes taxes & fees
9 Dec - 10 Dec
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Fridge, microwave, oven, stovetop
Hiker’s paradise! Come relax this summer!!!

Hiker’s paradise! Come relax this summer!!!

Roseland
10.0 out of 10, Exceptional, (36)
"Best place we have stayed around wintergreen hands down."
United States
Allen M.
Hiker’s paradise! Come relax this summer!!!
Smart TV, fireplace, video games, books
The newest and largest edition to the Wintergreen Retreat portfolio!

The newest and largest edition to the Wintergreen Retreat portfolio!

Wintergreen Resort
9.8 out of 10, Exceptional, (47)
"Beautiful property, well maintained. Perfect for a large group."
United States
Kenneth H.
The newest and largest edition to the Wintergreen Retreat portfolio!
Interior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen Resort
10.0 out of 10, Exceptional, (91)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is HK$911
HK$2,072 total
includes taxes & fees
9 Dec - 10 Dec
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Interior detail
Afton Mountain Vineyards

Afton Mountain Vineyards

2.5 star property
Afton
10.0 out of 10, Exceptional, (1)
"Amazing little cottage with everything you need. Loved the back porch and listening to music from the winery and enjoying the view. Good news, did not hear the music inside. "
United States
Kristin
The price is HK$2,725
HK$3,060 total
includes taxes & fees
9 Dec - 10 Dec
Afton Mountain Vineyards
Property grounds
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Wintergreen Resort
9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.
Property grounds
Cozy Cabin with private HOT TUB!

Cozy Cabin with private HOT TUB!

Nellysford
10.0 out of 10, Exceptional, (30)
"This location was a nice place to relax and enjoy family time."
United States
Melissa H.
Cozy Cabin with private HOT TUB!
Dining
Rustic Mountain Retreat-Bear Paw

Rustic Mountain Retreat-Bear Paw

Montebello
9.8 out of 10, Exceptional, (235)
"The river access is top notch. Great location near a bunch of hikes. A perfect, peaceful spot for a weekend. "
United States
John M.
Rustic Mountain Retreat-Bear Paw
Exterior
Wintergreen Oasis - PRIVATE POOL & SAUNA

Wintergreen Oasis - PRIVATE POOL & SAUNA

Nellysford
9.6 out of 10, Exceptional, (34)
"We enjoyed our stay"
United States
Miriam F.
Wintergreen Oasis - PRIVATE POOL & SAUNA
Exterior
Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail

Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail

Nellysford
10.0 out of 10, Exceptional, (4)
"Awesome property and location. We had a group with 11 adults and 8 kids. It was perfect for entertaining kids and adults. We will definitely book again."
United States
Peter T.
The price is HK$6,239
HK$10,860 total
includes taxes & fees
3 Jan - 4 Jan 2026
Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail
Outdoor dining
Mountain Views in Wintergreen

Mountain Views in Wintergreen

Laurel Ridge
10.0 out of 10, Exceptional, (9)
"We had a great trip! The house was beautiful with so much space! We loved using the hot tub at night. The host was helpful and responsive to all my questions. Would be happy to book this house again."
United States
Kara S.
Mountain Views in Wintergreen
Outdoor dining
Dragon's Back, 9BR 10BA in Wintergreen

Dragon's Back, 9BR 10BA in Wintergreen

Wintergreen Resort
Dragon's Back, 9BR 10BA in Wintergreen
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 Greenwood Hotel Reviews

Holiday Inn Express & Suites Charlottesville by IHG

Holiday Inn Express & Suites Charlottesville by IHG

10/10 Excellent
"Room was nice and clean"
Ari 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Charlottesville by IHG

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

  • View our selection of featured holiday rentals in Greenwood
  • Use the map to find apartments and other holiday homes in the Greenwood neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenwood while they last

Look no further and take a look at our great range of rental properties in Greenwood!

Frequently asked questions

Can I find holiday rentals in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing stay. Greenwood is known for its wineries.

What are some of the best holiday rentals that Greenwood has to offer?

Large and Luxurious Exec 5BR Chalet: This holiday home rental outside of Greenwood is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Greenwood?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Greenwood stay.

What’s there to see and do in Greenwood?

Explore the area and family-friendly sights such as War Fields, or get out into nature at a spot like Shenandoah National Park. In the wider area, you’ll find Pollak Vineyards and King Family Vineyards.

What’s a holiday rental in Greenwood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Greenwood. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips.