Title: Wintergreen Vacation Rentals from CA $306: Short-Term Rentals for 2026 | Expedia.ca

[Hotels in Wintergreen](https://expedia.ca/Wintergreen-Hotels.d10811.Travel-Guide-Hotels)[Things to do in Wintergreen](https://expedia.ca/Things-To-Do-In-Wintergreen.d10811.Travel-Guide-Activities)[Wintergreen Car Rentals](https://expedia.ca/Car-Rentals-In-Wintergreen.d10811.Car-Rental-Guide)[Wintergreen Vacation Packages](https://expedia.ca/Wintergreen.d10811.Destination-Travel-Guides)

![Everything is frozen over at Wintergreen Resort. ](https://images.trvl-media.com/place/553248635996625639/07d79deb-5cfc-4068-8e41-c17e7657b695.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Melissa Smestad

# Wintergreen Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Wintergreen vacation rentals

![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/ef5206ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/e60e6023.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/9e454f9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/eab7e1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

[](https://www.expedia.ca/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(1)

"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lloyd F.

CA $81

CA $261 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-First-Floor-Slopeside-Ski-In-Ski-Out-At-Wintergreen.h122831616.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/091549e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/d4f21770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/bd661df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/6fa06431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Escape to the Blue Ridge Mountains at Wine-tergreen! 

[](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information)

Wintergreen Resort

9.8/10

Exceptional

(123)

"The condo was very nice. Located on top of the mountain resort having spectacular views for the outlook just a short walk away. We will be boocking again for our next trip. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John

CA $147

CA $337 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Bouvet-Island-Hotels-Vrbo-Property.h43414813.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/81343878.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/w1003h683x0y0-5eec0b74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3c52de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/78b8767e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Laurelwood Hollow: Walk to Ski & Swim

[](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(2)

"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Alexander H.

CA $131

CA $384 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Nellysford-Hotels-Laurelwood-Hollow-Walk-To-Ski-Swim.h119304212.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/a870a931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/90-e785bc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, books](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/cda6931f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/bc03c18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information)

Roseland

9.6/10

Exceptional

(142)

"Great stay in Wintergreen!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Pete K.

CA $168

CA $362 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Charlottesville-Hotels-Pet-Friendly-Wintergreen-Piso-1BD-2BA-Reserva-Ahora-Para-La-Temporada-De-Esqui.h56543658.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/604129c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/e1d8c140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/f157e73a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/d40343ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information)

Roseland

9.8/10

Exceptional

(22)

"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Phil P.

CA $165

CA $339 total

includes taxes & fees

Dec 20 - Dec 21

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-1-Bedroom-Condo-Off-12th-Hole-At-Devils-Knob-Golf-Course.h95269237.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/8b86069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/e7802cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/b8f83d57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107860000/107854800/107854723/6989a232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bear Tracks Cottage: New Hot Tub + Fire Pit

[](https://www.expedia.ca/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information)

Nellysford

10/10

Exceptional

(30)

"Great location, beautiful home and so much to do nearby."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jordan D.

CA $252

CA $595 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-Bear-Tracks-Cottage-NEW-HOT-TUB-FIRE-PIT.h107854723.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/e57932c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/f81462f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/29fa29ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Modern Mountain Condo 

[](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(34)

"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelsey N.

CA $130

CA $321 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/eb46d699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/a92ed0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/c3acb08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/1b7442ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintergreen Condo -Steps to Ski and restaurants

[](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information)

Wintergreen Resort

9.8/10

Exceptional

(30)

"Had everything we needed, snacks and coffee were great for a cold weekend."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael L.

CA $157

CA $354 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-Wintergreen-Condo-Steps-To-Ski-And-Restaurants.h102325315.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/f8a3b378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, internet](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/abde4226.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/c029b4b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/79000000/78460000/78450300/78450238/1d0451ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pine Cottage: Hot Tub, 2 mins to Bold Rock!

[](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information)

Nellysford

10/10

Exceptional

(23)

"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jody W.

CA $260

CA $634 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-Pine-Cottage-Hot-Tub-And-Central-To-Nelson-151.h78450238.Hotel-Information)

![](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/b70b419a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/12a54ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/26d64274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information)

Roseland

9.0/10

Wonderful

(303)

"Great view!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Suzanne W.

CA $123

CA $306 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/6a8171b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/d81b69fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/70001ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/97000000/96720000/96718100/96718013/b46bd3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Condo in the Sky! Finest in Wintergreen!

[](https://www.expedia.ca/Nellysford-Hotels-Luxury-Condo-In-The-Sky-Finest-In-Wintergreen.h96718013.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(26)

"Great views"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Arpit N.

CA $206

CA $453 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-Luxury-Condo-In-The-Sky-Finest-In-Wintergreen.h96718013.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/b384df8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/79d4e134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/48c0e694.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintergreen. Sunset Vista Villa - Close to the ski slopes

[](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(92)

"Beautiful property! Had everything we needed and was very clean! Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Amanda W.

CA $161

CA $362 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/add548d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/w1021h678x3y3-264d8a13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/f9b08921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/57b1d668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4 BR cabin mins to trails & breweries pets welcome

[](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information)

Chestnut Springs

9.6/10

Exceptional

(28)

"Nice place and very clean "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Melad K.

CA $266

CA $805 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-4-BR-Cabin-Mins-To-Trails-Breweries-Pets-Welcome.h77100132.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/93f9d9bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/d176c035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/b003bae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/68a8e7c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

[](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(24)

"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cassie H.

CA $186

CA $479 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Nellysford-Hotels-Modern-Wintergreen-Retreat-3-Min-From-Slopes.h109092787.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/84000000/83660000/83655000/83654961/c3fb0c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83660000/83655000/83654961/d5c3968d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83660000/83655000/83654961/b37c3a5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83660000/83655000/83654961/b1159632.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bide-a-Wee- Hike the Trails! Close to the slopes!

[](https://www.expedia.ca/Roseland-Hotels-Bide-A-Wee-Hike-The-Trails-Close-To-The-Slopes.h83654961.Hotel-Information)

Wintergreen Resort

9.4/10

Exceptional

(11)

"very nice "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

claire b.

CA $289

CA $635 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Roseland-Hotels-Bide-A-Wee-Hike-The-Trails-Close-To-The-Slopes.h83654961.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/5c8096d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/7b8c9b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/41c181e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet, bed sheets](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/322fe5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Timbers Studio 46 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.Hotel-Information)

Wintergreen

10/10

Exceptional

(2)

"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Madison D.

CA $219

CA $368 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-Timbers-Studio-46-With-Wintergreen-Advantage.h102442095.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/5164314f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/8aa82274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/66529dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/a1aab594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serenity Cabin-Woodland Retreat

[](https://www.expedia.ca/Nellysford-Hotels-Serenity-Cabin-3-Bedroom-Woodland-Retreat-In-Wintergreen.h109542556.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(3)

"Great house and great host!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joe B.

CA $207

CA $558 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Nellysford-Hotels-Serenity-Cabin-3-Bedroom-Woodland-Retreat-In-Wintergreen.h109542556.Hotel-Information)

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/78744a11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/a54a7818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/85dceb55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/ddfb8915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain View Vista: Resort Condo w/ Views

[](https://www.expedia.ca/Nellysford-Hotels-NEW-Mountain-View-Vista-Resort-Condo-W-Views.h111307828.Hotel-Information)

Wintergreen Resort

9.4/10

Exceptional

(8)

"Beautiful view!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Serge L.

CA $191

CA $400 total

includes taxes & fees

Dec 18 - Dec 19

[](https://www.expedia.ca/Nellysford-Hotels-NEW-Mountain-View-Vista-Resort-Condo-W-Views.h111307828.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/f2101dda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/faaf96bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/40009d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119240000/119238400/119238386/7a98b6f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lofty Pursuits: Spectacular View + EV Charger

[](https://www.expedia.ca/Nellysford-Hotels-Lofty-Pursuits-Spectacular-View-EV-Charger.h119238386.Hotel-Information)

Treeloft

10/10

Exceptional

(4)

"Will definitely stay at this location again!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Richard W.

CA $234

CA $536 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Nellysford-Hotels-Lofty-Pursuits-Spectacular-View-EV-Charger.h119238386.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93330000/93321800/93321751/60351bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/94000000/93330000/93321800/93321751/d7add339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/94000000/93330000/93321800/93321751/b112549a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93330000/93321800/93321751/59a5c302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 4 BD Modern Cabin w/ Game Room + Golf Course View

[](https://www.expedia.ca/Nellysford-Hotels-4-BD-Modern-Cabin-W-Game-Room-Golf-Course-View.h93321751.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(2)

"Cozy cabin. Perfect for a quick family getaway! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kurt W.

CA $432

CA $934 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Nellysford-Hotels-4-BD-Modern-Cabin-W-Game-Room-Golf-Course-View.h93321751.Hotel-Information)

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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## Find vacation rentals that suit your style

Cabins

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Private vacation homes

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Aparthotels

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America&regionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America&regionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CONDO)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America&regionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=APARTMENT)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Wintergreen%2C+Virginia%2C+United+States+of+America&regionId=10811&latLong=37.884861%2C-78.899467&adults=2&startDate=2026-03-16&d1=2026-03-16&endDate=2026-03-19&d2=2026-03-19&lodging=CHALET)

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## Top Wintergreen Hotel Reviews

![Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! ](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/922abceb_y.jpg)

### Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026! 

10/10 Excellent

"We absolutely loved this condo, and especially the outstanding views.....a front row seat to gorgeous winter sunrises in your pjs! It was well equipped with everything one needs and was super cozy with a wood burning fireplace to boot. This 2 bedroom was perfect for 2 couples on a birthday weekend....an ideal spot for watching lots of football with beautiful views at every angle in the backdrop. The location is perfect, right across the street from the golf course, seconds from the Wintergarden, and just a few minutes from best sunset spot, Three Ridges Overlook on Devils Knob. We look forward to coming back. Maureen, our host, was wonderful and always available to answer any questions."

[](https://expedia.ca/Nellysford-Hotels-Best-Views-On-Mountain-Breathtaking-5-Star-Available-August-26-31-BOOK-NOW.h30501528.Hotel-Information)

![Wintergreen. Sunset Vista Villa - Sea of Mountains](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/3c2ad4b6_y.jpg)

### Wintergreen. Sunset Vista Villa - Sea of Mountains

10/10 Excellent

"We love staying at Sunset Vista, especially in December. The condo is clean and has everything we need to enjoy a weekend away. Rebecca and Matt are so helpful, quickly responding to all our questions and needs. Can't wait to go back. This year was extra beautiful with snow! "

[](https://expedia.ca/Charlottesville-Hotels-Stunning-Condo-Sunset-Vista-Villa.h68076715.Hotel-Information)

![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131_y.jpg)

### The Modern Mountain Condo 

10/10 Excellent

"Everything was perfect. Very welcoming, responsive, and clean. "

[](https://expedia.ca/Nellysford-Hotels-NEW-Modern-Mountain-Condo-WPool.h77096798.Hotel-Information)

![You deserve it all! Awesome Views, Comfy Condo & Elevator!](https://images.trvl-media.com/lodging/20000000/19630000/19624500/19624409/86699d42_y.jpg)

### You deserve it all! Awesome Views, Comfy Condo & Elevator!

10/10 Excellent

"The views are amazing. The host can also responds promptly if any questions. "

[](https://expedia.ca/Charlottesville-Hotels-You-Deserve-It-All-Awesome-Views.h19624409.Hotel-Information)

![Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop](https://images.trvl-media.com/lodging/34000000/33490000/33484800/33484712/31658c2d_y.jpg)

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

10/10 Excellent

"Home was well appointed and clean. Host was very helpful and timely in trying to get the TV's working - not being a "streamer", the process was new and frustrating.Enjoyed our stay - second time in this property. "

[](https://expedia.ca/Nellysford-Hotels-Wintergreen-Retreat-Bespoke-Luxury-Post-Beam-Home-On-Devils-Knob-Loop.h33484712.Hotel-Information)

![2br/2ba:  Million Dollar View from Luxury Condo on the Ridge.   ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/3ac798a2_y.jpg)

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

10/10 Excellent

"Gorgeous view. Our fourth time here, and still a lovely place. "

[](https://expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.Hotel-Information)

![New Build! Log Cabin with Hot Tub in Wintergreen](https://images.trvl-media.com/lodging/120000000/119320000/119318700/119318633/d3789b54_y.jpg)

### New Build! Log Cabin with Hot Tub in Wintergreen

10/10 Excellent

"Perfect place - thank you so much for letting us borrow your home!"

[](https://expedia.ca/Nellysford-Hotels-New-Build-Log-Cabin-With-Hot-Tub-In-Wintergreen.h119318633.Hotel-Information)

![Wow! What A View!](https://images.trvl-media.com/lodging/113000000/112620000/112613800/112613786/893db66c_y.jpg)

### Wow! What A View!

10/10 Excellent

"Everything was perfect. Loved the view"

[](https://expedia.ca/Nellysford-Hotels-Youll-Say-Wow-Over-This-View.h112613786.Hotel-Information)

![Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC](https://images.trvl-media.com/lodging/115000000/114430000/114424800/114424716/a7f8c534_y.jpg)

### Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

10/10 Excellent

"This Wintergreen condo was perfect for 2 couples. Very clean, beautiful views and well-equipped kitchen. Communication with host was timely, with clear check-in and out instructions. We stay on the Wintergreen ridge for our annual getaway and this place was great."

[](https://expedia.ca/Nellysford-Hotels-Cozy-2-Bedroom-Condo-With-Stunning-Views-Of-Lovely-Wintergreen-WiFi.h114424716.Hotel-Information)

## Find out more about Wintergreen

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wintergreen. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Condo Rentals in Wintergreen ](https://expedia.ca/Wintergreen-Condos.d10811-aaCondos.Travel-Guide-Accommodation)
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- [Cottages in Wintergreen ](https://expedia.ca/Wintergreen-Cottages.d10811-aaCottages.Travel-Guide-Accommodation)
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