Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Find vacation rentals that suit your style
Cabins
Apartments
Our top choices for Greenwood condo rentals
1. 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-friendlyRoseland
9.6 out of 10, Exceptional, (163 reviews)
"Perfect condo for couple. Two bathrooms, big kitchen, big porch, big living area."
Kathleen K.
$220 nightly
The price is $247
Nov 12 - Nov 13
Total with taxes and fees
2. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.
2 minutes from the shops and activities; Cozy 1 bedroom end unit.Wintergreen
9.4 out of 10, Exceptional, (129 reviews)
"Clean property that was well equipped, and easy check in."
Joseph Blaine
$205 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
3. 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, (338 reviews)
"We enjoyed our time at the stay. "
michael b.
$216 nightly
The price is $242
Nov 9 - Nov 10
Total with taxes and fees
4. Escape to the Blue Ridge Mountains at Wine-tergreen!
Escape to the Blue Ridge Mountains at Wine-tergreen!Wintergreen Resort
9.6 out of 10, Exceptional, (132 reviews)
"Close to Ski lifts and great for a weekend stay!"
Jennifer D.
$219 nightly
The price is $246
Nov 11 - Nov 12
Total with taxes and fees
5. Walk to Market/Private community outdoor pool!
Walk to Market/Private community outdoor pool!Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Enjoyed our stay."
Alice W.
$215 nightly
The price is $241
Nov 8 - Nov 9
Total with taxes and fees
6. Updated! Cozy and clean two bedroom condo.
Updated! Cozy and clean two bedroom condo.Wintergreen Resort
9.2 out of 10, Wonderful, (38 reviews)
"Great stay for my family!"
Joel M.
$215 nightly
The price is $241
Nov 12 - Nov 13
Total with taxes and fees
7. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • FireplaceWintergreen Resort
10.0 out of 10, Exceptional, (128 reviews)
"Nice condo in a nice resort. House has everything you need and more."
Thomas B.
$244 nightly
The price is $274
Nov 9 - Nov 10
Total with taxes and fees
8. Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Condo -Steps to Ski and restaurantsWintergreen Resort
9.8 out of 10, Exceptional, (39 reviews)
"It was a fine place for our family to stay during our staycation!"
Alicia G.
$257 nightly
The price is $289
Nov 7 - Nov 8
Total with taxes and fees
9. Unit 5 - Cozy Lower Level Studio Suite
Unit 5 - Cozy Lower Level Studio SuiteCharlottesville
10.0 out of 10, Exceptional, (35 reviews)
"Perfect for a short stay."
Gaye W.
$133 nightly
The price is $152
Nov 8 - Nov 9
Total with taxes and fees
10. Panoramic Peak
Panoramic PeakNellysford
10.0 out of 10, Exceptional, (1 review)
"The place was absolutely beautiful and spotless. The view was amazing. The only issue we had was when we asked where it was. We were told Nellysford and didn’t really understand that it was part of the Wintergreen resort so it was much further away from our actual destination. But the place was really amazing. We would stay there again."
Carrie
$263 nightly
The price is $295
Nov 23 - Nov 24
Total with taxes and fees
11. Northridge 07 With Wintergreen Advantage
Northridge 07 With Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
"Good Stay! Clean, need to have a lock on master bathroom. Door slides"
William M.
$237 nightly
The price is $266
Nov 8 - Nov 9
Total with taxes and fees
12. Diamond Hill Studio 09 with Wintergreen Advantage
Diamond Hill Studio 09 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great location and cozy condo! "
Molly M.
$228 nightly
The price is $256
Nov 8 - Nov 9
Total with taxes and fees
13. Luxury Condo in the Sky! Finest in Wintergreen!
Luxury Condo in the Sky! Finest in Wintergreen!Wintergreen Resort
10.0 out of 10, Exceptional, (48 reviews)
"Views were amazing!"
Sang Rea
14. Mountain Inn Studio 94 with Wintergreen Advantage
Mountain Inn Studio 94 with Wintergreen AdvantageWintergreen
$192 nightly
The price is $215
Nov 8 - Nov 9
Total with taxes and fees
15. Three Ridges 64 With Wintergreen Advantage
Three Ridges 64 With Wintergreen AdvantageChestnut Springs
$237 nightly
The price is $266
Nov 8 - Nov 9
Total with taxes and fees
16. Highridge Court 30 with Wintergreen Advantage
Highridge Court 30 with Wintergreen AdvantageChestnut Springs
10.0 out of 10, Exceptional, (1 review)
$255 nightly
The price is $287
Nov 8 - Nov 9
Total with taxes and fees
17. Cliffs 21 with Wintergreen Advantage
Cliffs 21 with Wintergreen AdvantageWintergreen
$255 nightly
The price is $287
Nov 9 - Nov 10
Total with taxes and fees
18. Mountain Inn Lodge 71 with Wintergreen Advantage
Mountain Inn Lodge 71 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, nice facilities.. polite staff "
Rich C.
$215 nightly
The price is $241
Nov 13 - Nov 14
Total with taxes and fees
19. Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort - Ski Slopes, Hike, Swim, & GolfWintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
Sarah L.
$256 nightly
The price is $288
Nov 9 - Nov 10
Total with taxes and fees
20. Mountain View Vista
Mountain View VistaNellysford
$266 nightly
The price is $299
Nov 15 - Nov 16
Total with taxes and fees
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.
Learn more about Greenwood
Escape to Greenwood! Enjoy its wineries.
Photo by Karyn Leary
Open Photo by Karyn Leary