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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)
The price is CA $154
CA $331 total
includes taxes & fees
Nov 18 - Nov 19

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)
The price is CA $138
CA $317 total
includes taxes & fees
Nov 8 - Nov 9

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)
The price is CA $131
CA $334 total
includes taxes & fees
Nov 9 - Nov 10

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)
The price is CA $162
CA $328 total
includes taxes & fees
Nov 15 - Nov 16

5. Updated! Cozy and clean two bedroom condo.
Updated! Cozy and clean two bedroom condo.Wintergreen Resort
9.2 out of 10, Wonderful, (38 reviews)
The price is CA $138
CA $323 total
includes taxes & fees
Nov 15 - Nov 16

6. Walk to Market/Private community outdoor pool!
Walk to Market/Private community outdoor pool!Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
The price is CA $138
CA $333 total
includes taxes & fees
Nov 8 - Nov 9

7. Panoramic Peak
Panoramic PeakNellysford
10.0 out of 10, Exceptional, (1 review)
The price is CA $242
CA $413 total
includes taxes & fees
Nov 23 - Nov 24

8. Northridge 07 With Wintergreen Advantage
Northridge 07 With Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
The price is CA $208
CA $372 total
includes taxes & fees
Nov 8 - Nov 9

9. Endless Mountain Top Views from All The Way Up!
Endless Mountain Top Views from All The Way Up!Wintergreen Resort
10.0 out of 10, Exceptional, (125 reviews)
The price is CA $227
CA $465 total
includes taxes & fees
Nov 8 - Nov 9

10. Three Ridges 64 With Wintergreen Advantage
Three Ridges 64 With Wintergreen AdvantageChestnut Springs
The price is CA $208
CA $372 total
includes taxes & fees
Nov 8 - Nov 9

11. 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)
The price is CA $226
CA $410 total
includes taxes & fees
Nov 15 - Nov 16

12. Mountain Inn Studio 94 with Wintergreen Advantage
Mountain Inn Studio 94 with Wintergreen AdvantageWintergreen
The price is CA $180
CA $298 total
includes taxes & fees
Nov 8 - Nov 9

13. Timbers Studio 14 with Wintergreen Advantage
Timbers Studio 14 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)

14. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & TrailsWintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
The price is CA $201
CA $440 total
includes taxes & fees
Nov 18 - Nov 19

15. Highridge Court 30 with Wintergreen Advantage
Highridge Court 30 with Wintergreen AdvantageChestnut Springs
10.0 out of 10, Exceptional, (1 review)
The price is CA $229
CA $401 total
includes taxes & fees
Nov 8 - Nov 9

16. 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)

17. Mountain View Vista
Mountain View VistaNellysford
The price is CA $247
CA $419 total
includes taxes & fees
Nov 16 - Nov 17

18. Vistas 71 with Wintergreen Advantage
Vistas 71 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
The price is CA $229
CA $401 total
includes taxes & fees
Nov 9 - Nov 10

19. Diamond Hill Studio 09 with Wintergreen Advantage
Diamond Hill Studio 09 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $222
CA $358 total
includes taxes & fees
Nov 8 - Nov 9

20. Overlook 180 degree views w/Peloton!
Overlook 180 degree views w/Peloton!Wintergreen Resort
9.4 out of 10, Exceptional, (3 reviews)
The price is CA $249
CA $545 total
includes taxes & fees
Nov 24 - Nov 25
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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Photo by Karyn Leary
Open Photo by Karyn Leary


































































