Title: Wintergreen Vacation Rentals from CA $323: Short-Term Rentals for 2026 | Expedia.ca

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Photo by Melissa Smestad

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## Check prices for these dates

In two weeks

[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)

In two months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-07-17&endDate=2026-07-19&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

![Exterior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/25cf6aa0.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)

![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)

![Interior](https://images.trvl-media.com/lodging/69000000/68080000/68076800/68076715/b384df8b.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 $168

CA $373 total

includes taxes & fees

Mar 29 - Mar 30

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

![Golf](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/6d550925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/57000000/56550000/56543700/56543658/132f64a4.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)

### 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 $152

CA $343 total

includes taxes & fees

Mar 29 - Mar 30

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

![Interior](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/eab7e1aa.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 $112

CA $301 total

includes taxes & fees

Mar 29 - Mar 30

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

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/502be393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/3cc1f40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/3fff845d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123220000/123217600/123217549/6f9b9681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Little Mountain Haven. True ski-in, ski-out. First floor!

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Studio-In-The-Fantastic-Wintergreen-Resort.h123217549.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(9 reviews)

"Great little ski and ski out Property"

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

Richard

CA $99

CA $285 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Studio-In-The-Fantastic-Wintergreen-Resort.h123217549.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)

![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)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119310000/119304300/119304212/4ae5f81b.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

(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 $131

CA $386 total

includes taxes & fees

Mar 29 - Mar 30

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

![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)

![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)

### The Modern Mountain Condo 

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

Wintergreen Resort

10/10

Exceptional

(46 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 $130

CA $323 total

includes taxes & fees

Mar 29 - Mar 30

[](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)

![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)

![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)

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

(32 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 $157

CA $369 total

includes taxes & fees

Mar 29 - Mar 30

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

![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)

![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)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27770000/27767700/27767679/64d05be3.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

(316 reviews)

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

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

Elaine B.

CA $143

CA $348 total

includes taxes & fees

Mar 29 - Mar 30

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

![Exterior](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/w1280h851x0y2-5d255bac.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)

![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/142bac58.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

(36 reviews)

"Great"

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

Daniel W.

CA $196

CA $544 total

includes taxes & fees

Mar 30 - Mar 31

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

![Dining](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/4a80edab.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)

### Panoramic Peak: Wintergreen Condo with Views

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

Wintergreen Resort

9.6/10

Exceptional

(40 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 $192

CA $405 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Nellysford-Hotels-Panoramic-Peak-Wintergreen-Condo-With-Views.h90233005.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/96000000/95270000/95269300/95269237/200109ab.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)

### 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)

"Great condo and n the Wintergreen area. Absolutely beautiful with the fall foliage colors. Close to so many breweries and wineries."

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

Anna D.

CA $166

CA $344 total

includes taxes & fees

Mar 30 - Mar 31

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

![Property grounds](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/07c4a1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/89b7b76d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/02bbf7d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Wintergreen Resort

10/10

Exceptional

(99 reviews)

"Highly recommend staying at this beautiful condo! The kitchen has everything you need, the views are breath-taking, the condo is very clean, and the hosts are very communicative and helpful. Will definitely stay here again the next time we travel to the area!"

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

Allison N.

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

![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)

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

### 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 $160

CA $355 total

includes taxes & fees

Mar 31 - Apr 1

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

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

![TV, fireplace](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/d370f505.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 $192

CA $405 total

includes taxes & fees

Mar 29 - Mar 30

[](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/110000000/109100000/109092800/109092787/6767c599.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/110000000/109100000/109092800/109092787/485372ad.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 $162

CA $455 total

includes taxes & fees

Mar 29 - Mar 30

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

![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)

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

![Interior](https://images.trvl-media.com/lodging/92000000/91340000/91333300/91333207/3abeba53.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 $214

CA $447 total

includes taxes & fees

Mar 29 - Mar 30

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

![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/cc117128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/48db9b15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/6eff1174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/c8e58b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

[](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(29 reviews)

"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "

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

Jeremiah H.

CA $158

CA $468 total

includes taxes & fees

Mar 29 - Mar 30

[](https://www.expedia.ca/Nellysford-Hotels-New-Listing-3-Min-To-Ski-Whot-Tub-And-Fireplace-Dog-Friendly.h90127668.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)

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

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/110000000/109350000/109347300/109347289/w1199h797x1y1-4e7a5a6f.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)

### 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 $186

CA $450 total

includes taxes & fees

Mar 29 - Mar 30

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/3e6d7427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/5a21de65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/c23d20f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, internet](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/747eed18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Inn Studio 96 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Studio-96-With-Wintergreen-Advantage.h102442025.Hotel-Information)

Wintergreen

10/10

Exceptional

(1 review)

"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "

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

Lana

CA $178

CA $313 total

includes taxes & fees

Mar 28 - Mar 29

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Inn-Studio-96-With-Wintergreen-Advantage.h102442025.Hotel-Information)

![Cabin, Private Bathroom (Blackwood Chalet) | Lounge](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/cbf52e3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, Private Bathroom (Blackwood Chalet) | Exterior](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/cb763d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, Private Bathroom (Blackwood Chalet) | Exterior](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/f99d2e26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin, Private Bathroom (Blackwood Chalet) | Lounge](https://images.trvl-media.com/lodging/112000000/111090000/111087800/111087718/w1024h662x0y21-0ba6e6d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Blackwood Chalet

[](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.Hotel-Information)

Nellysford

10/10

Exceptional

(3 reviews)

"Love the area"

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

Toni

[](https://www.expedia.ca/Nellysford-Hotels-Blackwood-Chalet.h111087718.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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-04-10&endDate=2026-04-11&regionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Cabins

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Condos

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Cottages

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Aparthotels

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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=2026-06-24&d1=2026-06-24&endDate=2026-06-27&d2=2026-06-27&lodging=CHALET)

Apartments

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## Top Wintergreen Hotel Reviews

![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)

![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)

![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

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

[](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

"We had a wonderful time! The condo was perfect for our family of 4 with 2 small dogs. The condo was clean, well laid out, and very well stocked. It had everything we needed and more! The communication with the host was super fast and helpful. We already booked for next year!"

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

![Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort](https://images.trvl-media.com/lodging/117000000/116730000/116728200/116728114/552218fd_y.jpg)

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

10/10 Excellent

"The most breathtaking view! Easy communication, clean, and very comfortable. We will definitely be back!"

[](https://expedia.ca/Nellysford-Hotels-Breathtaking-Mountain-Views-In-A-2-Bedroom-Condo-At-Wintergreen-Resort.h116728114.Hotel-Information)

![Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope](https://images.trvl-media.com/lodging/73000000/72040000/72035400/72035303/w1280h851x0y3-1cfe3ccf_y.jpg)

### Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

10/10 Excellent

"Very nice house right near everything you want at wintergreen. Host was very responsive to messages and the house was extremely clean and well cared for."

[](https://expedia.ca/Nellysford-Hotels-Fantastic-Mountain-Views-Walk-To-Ski-Slopes-Modern-Luxury-Wintergreen-Home.h72035303.Hotel-Information)

![Upscale and Family-Friendly in Wintergreen](https://images.trvl-media.com/lodging/97000000/96500000/96498900/96498850/31eb2d68_y.jpg)

### Upscale and Family-Friendly in Wintergreen

8/10 Good

"The house was big,comfortable and clean. We appreciated being able to bring our pets too.The hot tub was hot but was a bit dirty. Our family enjoyed the sauna and deck area and had a wonderful stay!"

[](https://expedia.ca/Nellysford-Hotels-Upscale-And-Family-Friendly-In-Wintergreen.h96498850.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

"This condo was exceptional. It was clean and exactly as pictured in the photos. The beds were comfortable and we appreciated a pantry with basic staples. The best part was the views. You could see for miles across the Blue Ridge mountains. The hosts were also great about checking in and making sure everything was okay. I really appreciated the personal touches they put in the place, including a guide that went over the local area. I would highly recommend this place and would definitely stay again. "

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

![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

"Very clean, gorgeous views"

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