Title: Wintergreen Vacation Rentals from CA $325: Short-Term Rentals for 2026 | Expedia.ca

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Photo by Melissa Smestad

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

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## Check prices for these dates

In two weeks

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jun 5 - Jun 7](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jul 3 - Jul 5](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 31 - Aug 2](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-07-31&endDate=2026-08-02&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

![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/eb46d699.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)

![Interior](https://images.trvl-media.com/lodging/103000000/102330000/102325400/102325315/55159b64.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)

### 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

(33 reviews)

"Check in was a breeze, amazing location and great nights stay."

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

Garrett P.

CA $159

CA $372 total

includes taxes & fees

Apr 8 - Apr 9

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

![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/dda1ec86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/d5c938fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Golf](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/6d550925.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

(149 reviews)

"Very clean and pet-friendly "

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

Heston

CA $153

CA $345 total

includes taxes & fees

Apr 8 - Apr 9

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

![Exterior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/25cf6aa0.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/69000000/68080000/68076800/68076715/319b2ae2.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. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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

Wintergreen Resort

10/10

Exceptional

(105 reviews)

"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"

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

Vicki E.

CA $188

CA $400 total

includes taxes & fees

Apr 13 - Apr 14

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

![Exterior](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/3f379aa5.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)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/4ae5f81b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/c99efe6c.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

(8 reviews)

"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 $150

CA $409 total

includes taxes & fees

Apr 8 - Apr 9

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

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/9bc2c3df.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/112000000/111310000/111307900/111307828/956722d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/5599d561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/6da2f0a0.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

(12 reviews)

"Beautiful view!"

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

Serge L.

CA $193

CA $408 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/1b87e3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/485372ad.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/110000000/109100000/109092800/109092787/6767c599.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

(34 reviews)

"Cozy, clean very attentive host Paul was amazingThis cozy kid friendly family home was very accommodating. Def will be back again!!"

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

Pamela P.

CA $144

CA $434 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109350000/109347300/109347289/w1199h809x1y1-e64db49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109350000/109347300/109347289/w1200h798x0y1-48c7360f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/110000000/109350000/109347300/109347289/w1200h797x0y1-837dbc90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109350000/109347300/109347289/w1200h797x0y1-8e27a433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Wintergreen-Condo.h109347289.Hotel-Information)

Wintergreen Resort

9.4/10

Exceptional

(14 reviews)

"We enjoyed our stay here. Brought the whole family."

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

Caroline D.

CA $188

CA $453 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Wintergreen-Condo.h109347289.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)

![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)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/e9ccaff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/200109ab.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

(30 reviews)

"Wonderful cozy condo close to the golf course and the slopes. "

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

Deborah R.

CA $167

CA $347 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/9ebdff32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/f62c61a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/b937af11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/w1280h851x0y2-5d255bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Diamond Adventure at Wintergreen Resort \*FULLY UPDATED\*

[](https://www.expedia.ca/Nellysford-Hotels-Diamond-Adventure-At-Wintergreen-Resort.h76980781.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(38 reviews)

"Amazing Condo and owner. Great access to slopes, well appointed and clean. Beautiful views and can walk to everything in the heart of the resort "

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

Patrick E.

CA $198

CA $552 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Diamond-Adventure-At-Wintergreen-Resort.h76980781.Hotel-Information)

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

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

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/2c7ab499.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)

### 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

(11 reviews)

"Great house and great host!"

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

Joe B.

CA $161

CA $532 total

includes taxes & fees

Apr 8 - Apr 9

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

![Fireplace](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/0d2cf0fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/53d40131.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

(47 reviews)

"The property was just as described and the communication was a breeze. The view from the unit’s deck was beautiful. "

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

Susan

CA $131

CA $325 total

includes taxes & fees

Apr 8 - Apr 9

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

![TV, fireplace](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/cc6d8205.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/1c6b26da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/02b37b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/965ee1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wintergreen Resort Condo Available Now!!

[](https://www.expedia.ca/Nellysford-Hotels-Ready-For-Ski-Season-Book-NOW.h91333207.Hotel-Information)

Wintergreen Resort

9.8/10

Exceptional

(25 reviews)

"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "

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

Pam M.

CA $216

CA $450 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Ready-For-Ski-Season-Book-NOW.h91333207.Hotel-Information)

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

![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/4641225d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/254bda6d.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

(317 reviews)

"I love this place!!! Will book again everytime we are there!"

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

Thavikiet T.

CA $144

CA $351 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Nellysford-Hotels-2br2ba-Million-Dollar-View-From-Luxury-Condo-On-The-Ridge.h27767679.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/44000000/43420000/43414900/43414813/6fa06431.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)

![Interior](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/d10f5f40.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

(126 reviews)

"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "

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

David L.

CA $162

CA $358 total

includes taxes & fees

Apr 8 - Apr 9

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

![1 bedroom, desk, internet, bed sheets](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/d991cebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/29d540e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/bc698b19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/4a80edab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Panoramic Peak: Wintergreen Condo with Views

[](https://www.expedia.ca/Nellysford-Hotels-Panoramic-Peak-Wintergreen-Condo-With-Views.h90233005.Hotel-Information)

Wintergreen Resort

9.8/10

Exceptional

(41 reviews)

"The location was great and the sunrise views were amazing!"

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

Jennifer B.

CA $193

CA $408 total

includes taxes & fees

Apr 12 - Apr 13

[](https://www.expedia.ca/Nellysford-Hotels-Panoramic-Peak-Wintergreen-Condo-With-Views.h90233005.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/8543bb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/1751da82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/a4bff7e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442100/38271547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Diamond Hill Studio 09 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Diamond-Hill-Studio-09-With-Wintergreen-Advantage.h102442100.Hotel-Information)

Wintergreen

10/10

Exceptional

(2 reviews)

"Great location and cozy condo! "

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

Molly M.

CA $221

CA $375 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Diamond-Hill-Studio-09-With-Wintergreen-Advantage.h102442100.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/c12a7e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/a15eafd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/9b156d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/89000000/88080000/88074700/88074679/7b798769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious + Serene Mtn Top Escape, 4 En Suites

[](https://www.expedia.ca/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(54 reviews)

"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."

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

James S.

CA $93

CA $475 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Spacious-Serene-Mtn-Top-Escape.h88074679.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441921/14701ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441921/5eb09382.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441921/36fe38ba.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/103000000/102450000/102442000/102441921/adfa5a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Inn Lodge 54 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Lodge-54-With-Wintergreen-Advantage.h102441921.Hotel-Information)

Wintergreen

10/10

Exceptional

(3 reviews)

"We were in the area looking to possibly relocate and this loft on the mountain was a beautiful stay. Convenient to restaurants within walking distance. We would definitely book again!"

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

Erin C.

CA $193

CA $351 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Lodge-54-With-Wintergreen-Advantage.h102441921.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/ae35c88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/403fa3ca.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/123000000/122840000/122831700/122831616/3e9a531d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/b56e2b25.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

(13 reviews)

"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 $113

CA $303 total

includes taxes & fees

Apr 12 - Apr 13

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

![Exterior](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/820fcb7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/790a2a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/cd4f8621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/120000000/119550000/119543400/119543302/0cbe3407.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Three Ridges 64 With Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-64-With-Wintergreen-Advantage.h119543302.Hotel-Information)

Chestnut Springs

CA $228

CA $421 total

includes taxes & fees

Apr 8 - Apr 9

[](https://www.expedia.ca/Nellysford-Hotels-Three-Ridges-64-With-Wintergreen-Advantage.h119543302.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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Condos

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Cottages

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Aparthotels

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Private vacation homes

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Apartments

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Chalets

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## Top Wintergreen Hotel Reviews

![WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS](https://images.trvl-media.com/lodging/49000000/48840000/48830800/48830715/2a174ad4_y.jpg)

### WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10/10 Excellent

"Della was amazing and allowed for an early check in once the condo was cleaned and ready for us, which was much appreciated after traveling with a toddler. She was very responsive and helpful throughout our stay. Place has everything you need and gorgeous views. The deer even came up to our window one morning! "

[](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Resort-Home-With-Blue-Ridge-Views.h48830715.Hotel-Information)

![The Modern Mountain Condo ](https://images.trvl-media.com/lodging/78000000/77100000/77096800/77096798/w1273h849x4y3-b64d948a_y.jpg)

### The Modern Mountain Condo 

10/10 Excellent

"This was an amazing cozy place for the weekend. Everything is near by and easy to get to. The kit hen is well stocked for cooking, and the back porch was lovely to sit on. "

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

![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/6e5f684e_y.jpg)

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

10/10 Excellent

"Perfect vacation getaway in the heart of Wintergreen Resort."

[](https://expedia.ca/Charlottesville-Hotels-Wintergreen-Pet-Friendly-Condo-Wwifi.h29852618.Hotel-Information)

![Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14](https://images.trvl-media.com/lodging/52000000/51800000/51793700/51793663/4496093e_y.jpg)

### Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

10/10 Excellent

"Great home with amazing view of the sunrise."

[](https://expedia.ca/Nellysford-Hotels-Stunning-Newly-Rebuilt-Home-Perfect-Peaceful-Getaway-That-Sleeps-14.h51793663.Hotel-Information)

![Wintergreen. Sunset Vista Villa - Close to the ski slopes](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/25cf6aa0_y.jpg)

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

10/10 Excellent

"My two sisters and I got away to the mountains for a weekend and I'm so glad I found Sunset Vista! The condo was absolutely perfect! It was so well appointed, had a beautiful "large" balcony where we were able to see amazing sunsets. It was clean, the beds were very comfortable and it was so close to local wineries and breweries.Our host, Rebecca was so responsive and accommodating!We can't wait to visit again and no need to look at another property - Sunset Vista is it!"

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

![Endless Mountain Top Views from All The Way Up!](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7_y.jpg)

### Endless Mountain Top Views from All The Way Up!

10/10 Excellent

"As advertised, the view was amazing. We appreciated all the conveniences of paper products, toiletries, kitchen items. Very enjoyable trip and accomodations comfortable for 2 couples. Great location for MANY wineries, breweries, distilleries. Had a gorgeous day to see Natural Bridge."

[](https://expedia.ca/Nellysford-Hotels-Endless-Mountain-Top-Views-From-All-The-Way-Up.h90087205.Hotel-Information)

![Cozy Cabin with private HOT TUB!](https://images.trvl-media.com/lodging/59000000/58990000/58985800/58985753/90-636eaa8c_y.jpg)

### Cozy Cabin with private HOT TUB!

10/10 Excellent

"The host is very responsive. Cute rustic cabin. Close to resort, hiking trails and scenic overlooks. "

[](https://expedia.ca/Nellysford-Hotels-Cozy-Cabin-With-Private-HOT-TUB.h58985753.Hotel-Information)

![Best views on Mountain! Breathtaking 5 Star condo! EASTER STILL AVAILABLE!](https://images.trvl-media.com/lodging/31000000/30510000/30501600/30501528/f17119a4_y.jpg)

### Best views on Mountain! Breathtaking 5 Star condo! EASTER STILL AVAILABLE!

10/10 Excellent

"We had a lovely and comfortable stay with beautiful views!"

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

![2br/2ba:  Million Dollar View from Luxury Condo on the Ridge.   ](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/254bda6d_y.jpg)

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

10/10 Excellent

"As advertised, the view was amazing and the sunrise was so beautiful over the mountains. We really enjoyed having a fire on a rainy Monday and being able to go out to lunch without leaving the resort. Really close to the Blue Ridge Parkway and some lovely walks right in the resort. Thanks for a great weekend getaway!"

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