Title: Wintergreen Vacation Home Rentals from CA $203: Search Top Private Vacation Homes for Rent | Expedia.ca

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![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

![](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

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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)

In three months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=10811&startDate=2026-05-08&endDate=2026-05-10&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four 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)

## Our top choices for Wintergreen vacation homes

![Exterior](https://images.trvl-media.com/lodging/91000000/90130000/90127700/90127668/cc117128.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)

![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)

![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)

### 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

(26 reviews)

"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"

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

Courtney S.

CA $174

CA $484 total

includes taxes & fees

Mar 12 - Mar 13

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/0b37c703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/d430d622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/c6b5a028.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90930000/90923900/90923831/bc42cfa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful 4-season Mountain Home- New Listing

[](https://www.expedia.ca/Nellysford-Hotels-Beautiful-4-Season-Mountain-Home-New-Listing.h90923831.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(43 reviews)

"The property is clean, bed rooms are spacious. 3.5 bath, kitchen has latest appliances, bedding & accessories are star hotel standard. We loved our stay. "

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

Mridul G.

CA $271

CA $739 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Nellysford-Hotels-Beautiful-4-Season-Mountain-Home-New-Listing.h90923831.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/3c9bf26c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/800464dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/dbb42ada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112400000/112394300/112394246/2e09623c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### "Glass & Pine" Home close to Bold Rock & Vineyards

[](https://www.expedia.ca/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information)

Nellysford

10/10

Exceptional

(2 reviews)

"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "

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

Robert H.

CA $236

CA $564 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Nellysford-Hotels-Glass-Pine-Home-Close-To-Bold-Rock-Vineyards.h112394246.Hotel-Information)

![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)

![Dining](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/05a5f823.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)

![Exterior](https://images.trvl-media.com/lodging/78000000/77110000/77100200/77100132/2360dc20.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

(29 reviews)

"Nice place and very clean "

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

Melad K.

CA $263

CA $805 total

includes taxes & fees

Mar 9 - Mar 10

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

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/72000000/72000000/71991100/71991030/00cee117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/72000000/71991100/71991030/9c3ba9c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/72000000/71991100/71991030/aade01b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/72000000/72000000/71991100/71991030/6b89109a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Above the Clouds! Perfect Escape for Families!

[](https://www.expedia.ca/Nellysford-Hotels-Enjoy-The-Mountain-Air-When-You-Stay-At-The-Retreat-At-Wintergreen.h71991030.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(21 reviews)

"We absolutely loved our stay at Brett’s cabin. It is very spacious and clean, has 2 fireplaces and an outdoor fire pit, ample sitting areas, and had everything we needed to enjoy a weekend in wintergreen. We are hoping to return soon!"

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

Andrea M.

CA $477

CA $953 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Nellysford-Hotels-Enjoy-The-Mountain-Air-When-You-Stay-At-The-Retreat-At-Wintergreen.h71991030.Hotel-Information)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/3eb2493c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/ee6d125e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets, wheelchair access](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/0197d413.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, offices](https://images.trvl-media.com/lodging/113000000/112540000/112532200/112532111/495338f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Distinguished Squirrel Chalet walking distance

[](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information)

Treeloft

9.0/10

Wonderful

(10 reviews)

"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "

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

Ryan R.

CA $345

CA $736 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Nellysford-Hotels-The-Distinguished-Squirrel-Chalet-Walking-Distance.h112532111.Hotel-Information)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/75000000/74070000/74065000/74064991/420c971b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74070000/74065000/74064991/52ae84dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/75000000/74070000/74065000/74064991/d8931f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/75000000/74070000/74065000/74064991/730d89e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whiskey Ridge - Luxury Mountaintop Family Retreat \* Dog Friendly \* Hot Tub

[](https://www.expedia.ca/Nellysford-Hotels-Luxury-Mountaintop-Family-Retreat.h74064991.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(10 reviews)

"House had everything we could possibly want. The layout was perfect for teens to have their own space."

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

Jessica S.

CA $393

CA $955 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Nellysford-Hotels-Luxury-Mountaintop-Family-Retreat.h74064991.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/dccda057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/a56af0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/8c2f2f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109800000/109793400/109793345/91c362f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ridge Retreat @ Wintergreen!

[](https://www.expedia.ca/Roseland-Hotels-Ridge-Retreat-Wintergreen.h109793345.Hotel-Information)

Wintergreen Resort

9.6/10

Exceptional

(5 reviews)

"Beautiful home and it has everything you need for a get-a-way. Five couples and plenty of room to have your own space. Close to lots of recreation and entertainment. "

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

Robert J.

CA $338

CA $1,033 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Roseland-Hotels-Ridge-Retreat-Wintergreen.h109793345.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110893400/110893388/d189b6c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110900000/110893400/110893388/e9796846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/111000000/110900000/110893400/110893388/cbc9b621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110900000/110893400/110893388/1580ba8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### ​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub

[](https://www.expedia.ca/Nellysford-Hotels-6BR-Designer-Home-With-Epic-Backyard-In-Wintergreen-Resort.h110893388.Hotel-Information)

Chestnut Springs

10/10

Exceptional

(7 reviews)

"Wonderful house and host! "

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

Alyshia F.

[](https://www.expedia.ca/Nellysford-Hotels-6BR-Designer-Home-With-Epic-Backyard-In-Wintergreen-Resort.h110893388.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/b52d4b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/f7278c9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/e128d489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/112000000/112000000/111999900/111999850/a4330528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

[](https://www.expedia.ca/Nellysford-Hotels-Spacious-5-Bedroom-Modern-Home-With-Mountain-Views-Galore-Sauna-EV-Charger.h111999850.Hotel-Information)

Nellysford

10/10

Exceptional

(5 reviews)

"We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!"

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

Rachel F.

CA $409

CA $1,084 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Nellysford-Hotels-Spacious-5-Bedroom-Modern-Home-With-Mountain-Views-Galore-Sauna-EV-Charger.h111999850.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/117000000/116430000/116427300/116427236/3d285c2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/117000000/116430000/116427300/116427236/cc00949e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116430000/116427300/116427236/99469e17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116430000/116427300/116427236/b699cfa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Views, Hot Tub, Impeccable Design

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Views.h116427236.Hotel-Information)

Wintergreen Resort

9.2/10

Wonderful

(5 reviews)

"Lovely house with a great view! Highly recommend!"

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

Ron S.

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Views.h116427236.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101430000/101420600/101420502/dd6510e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/102000000/101430000/101420600/101420502/57090202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/102000000/101430000/101420600/101420502/w1439h1800x0y0-77795e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/102000000/101430000/101420600/101420502/b3b9d27f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!

[](https://www.expedia.ca/Roseland-Hotels-Cozy-Lodge-With-View-Wintergreen-Ski-Chalet-Walk-To-Slopes-Family-Friendly.h101420502.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(6 reviews)

"We had a wonderful stay. It was 8 of us and the place was nicely decorated, comfortable, clean and well stocked. Would stay here again. "

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

N P.

CA $272

CA $667 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Roseland-Hotels-Cozy-Lodge-With-View-Wintergreen-Ski-Chalet-Walk-To-Slopes-Family-Friendly.h101420502.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/c2bc8240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/05b23c92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/a45b898b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118800000/118792500/118792404/d3cfafa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

[](https://www.expedia.ca/Nellysford-Hotels-Updated-Mtn-House-2-Mins-To-Resort-3King-Beds.h118792404.Hotel-Information)

Laurel Ridge

10/10

Exceptional

(4 reviews)

"Fabulous house and we all had a great time! "

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

Mindy M.

CA $419

CA $1,252 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Nellysford-Hotels-Updated-Mtn-House-2-Mins-To-Resort-3King-Beds.h118792404.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/118000000/117160000/117151700/117151670/de42f46c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/118000000/117160000/117151700/117151670/019651c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117160000/117151700/117151670/9ba27402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117160000/117151700/117151670/9e0b95ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mountain Views in Wintergreen

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Views-In-Wintergreen.h117151670.Hotel-Information)

Laurel Ridge

10/10

Exceptional

(12 reviews)

"We really enjoyed our stay with friends and family. Plenty of room to accommodate multiple families and kids. Would stay here again."

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

Chase F.

CA $643

CA $1,340 total

includes taxes & fees

Feb 23 - Feb 24

[](https://www.expedia.ca/Nellysford-Hotels-Mountain-Views-In-Wintergreen.h117151670.Hotel-Information)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/42ee1156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/22047e16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/f6b9d806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/73000000/72100000/72098800/72098776/cce1d2b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

[](https://www.expedia.ca/Nellysford-Hotels-Black-Bear-Lodge-Wintergreen-Sleeps-12-5bd4ba-Ski-Sky-More-Space-To-Play.h72098776.Hotel-Information)

Pedlars Edge

9.8/10

Exceptional

(33 reviews)

"The house was great! It was very clean and spacious, and also accessible to older grandparents who use walkers. And the view from the deck is fantastic, particularly with the fall colors. We really enjoyed the activities at Wintergreen, including walking/hiking trails and the riding the chairlift to see fall foliage. We had a great stay! "

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

Randy S.

CA $511

CA $1,066 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Nellysford-Hotels-Black-Bear-Lodge-Wintergreen-Sleeps-12-5bd4ba-Ski-Sky-More-Space-To-Play.h72098776.Hotel-Information)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/9686cc2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/1cef43e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/e325d9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95420000/95414800/95414737/d6c7475a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Serene Wintergreen Retreat, Nestled in the Trees

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Home-In-Wintergreen-Close-To-Ski-Slopes.h95414737.Hotel-Information)

Wintergreen Resort

9.6/10

Exceptional

(18 reviews)

"A great weekend stay with our guests and family as well as the dogs! The only thing I could find to complain about was that the balcony area was piled with leaves when we arrived but other than that it wasn't much of a bother. The kids had fun throwing the leaves back into the woods. It was spacious and our host was very communicative. Would come to stay again!"

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

Samantha Mae S.

CA $929

CA $1,661 total

includes taxes & fees

Mar 14 - Mar 15

[](https://www.expedia.ca/Nellysford-Hotels-Cozy-Mountain-Home-In-Wintergreen-Close-To-Ski-Slopes.h95414737.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/34f30416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/202ad8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/89e1bc03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71280000/71271600/71271547/5972c422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whole House

[](https://www.expedia.ca/Amherst-Hotels-Whole-House.h71271547.Hotel-Information)

Amherst

9.6/10

Exceptional

(35 reviews)

"Nice house!!"

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

Tracy T.

CA $123

CA $203 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Amherst-Hotels-Whole-House.h71271547.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/66c9e85e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/dfedc5d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/c2e9d716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/79000000/78650000/78647300/78647228/620df162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### NEW! Cheerful 2 bd bungalow with hot tub. Must see!

[](https://www.expedia.ca/Waynesboro-Hotels-NEW-Cheerful-2-Bd-Bungalow-With-Hot-Tub-Must-See.h78647228.Hotel-Information)

Waynesboro

9.8/10

Exceptional

(46 reviews)

"loved the quiet location, sunny private back yard, and well-stocked kitchen"

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

George D.

CA $159

CA $279 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Waynesboro-Hotels-NEW-Cheerful-2-Bd-Bungalow-With-Hot-Tub-Must-See.h78647228.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/84bbbc13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/ce44437f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/c12d991d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83020000/83010900/83010856/2c0e912e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hillside Haven: Modern Retreat, Mountain Views

[](https://www.expedia.ca/Faber-Hotels-Hillside-Haven-Modern-Retreat.h83010856.Hotel-Information)

Faber

10/10

Exceptional

(33 reviews)

"Fantastic property with all the amenities near UVA, and lots of wineries."

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

roberto c.

CA $244

CA $572 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Faber-Hotels-Hillside-Haven-Modern-Retreat.h83010856.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/e65b3395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/2b941ca3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/977401aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/104000000/103170000/103166000/103165960/4cf77170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

[](https://www.expedia.ca/Nellysford-Hotels-NEWTucked-Inn-Upper-Unit-151-Getaway.h103165960.Hotel-Information)

Nellysford

10/10

Exceptional

(6 reviews)

"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "

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

Katie K.

CA $161

CA $431 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Nellysford-Hotels-NEWTucked-Inn-Upper-Unit-151-Getaway.h103165960.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=2026-03-01&endDate=2026-03-02&regionId=10811&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN)

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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE)

Private vacation homes

[](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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME)

Aparthotels

[](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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL)

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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO)

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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CHALET)

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=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT)

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## Top Wintergreen Hotel Reviews

![Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️](https://images.trvl-media.com/lodging/41000000/40900000/40894200/40894108/228cd4e3_y.jpg)

### Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10/10 Excellent

"This is a beautiful home in an excellent location, conveniently situated near ski school and the beginner slopes. The property was exceptionally clean and offered a warm, inviting atmosphere. The owner was highly responsive, friendly, and accommodating throughout our stay. We look forward to returning in the future."

[](https://expedia.ca/Charlottesville-Hotels-New-To-The-Market.h40894108.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

"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"

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

![Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall](https://images.trvl-media.com/lodging/68000000/67620000/67610200/67610139/337b5b81_y.jpg)

### Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

10/10 Excellent

"Very easy check in & out with clear instructions. Condo was in a great location, was clean and comfortable, and had everything we needed!"

[](https://expedia.ca/Nellysford-Hotels-2-Bedroom-Condo-At-The-Top-Of-The-Mountain.h67610139.Hotel-Information)

![Serenity Cabin-Woodland Retreat](https://images.trvl-media.com/lodging/110000000/109550000/109542600/109542556/5164314f_y.jpg)

### Serenity Cabin-Woodland Retreat

10/10 Excellent

"This was a wonderful place for family and friends. The host was very responsive, the kitchen was well stocked and the beds and linens were very comfortable! The location was perfect and close to the slopes. A fantastic stay in a fantastic cabin! "

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

"Troy was the best!"

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

"Cozy condo with beautiful sunrise view of the mountain. Loved the relaxing atmosphere and the shuttle access to the main lodge. Would love to stay again for another visit. "

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

![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

"Fantastic views! Gorgeous setting. Comfortable beds and furniture. Spacious and well-appointed. We will be back soon. Maureen is also a delight and made us feel right at home. "

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

![Diamond Adventure at Wintergreen Resort *FULLY UPDATED*](https://images.trvl-media.com/lodging/77000000/76990000/76980800/76980781/e36b50fc_y.jpg)

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

10/10 Excellent

"It was perfect and as described! Great location, great view of one of the main ski runs. Seemed to be updated recently and super clean! The massage chair is a GREAT Touch after you are done skiing. Couldn't recommend this place any higher, It was Great!"

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

![Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d_y.jpg)

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

10/10 Excellent

"This is our 4th stay at this condo and as always it’s been clean and cozy. We love it here and will be back soon! "

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

## Find out more about Wintergreen

## Wintergreen Vacation Homes information

| Number of reviews | 351                |
| ----------------- | ------------------ |
| Accommodation     | 197 Vacation Homes |
| Lowest Price      | CA $203            |
| Highest Price     | CA $1,252          |

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- [Flights to Stuarts Draft ](https://www.expedia.ca/Cheap-Flights-To-Stuarts-Draft.d6056908.Travel-Guide-Flights)
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- [Flights from Covesville ](https://www.expedia.ca/lp/flights/3000355074/flights-from-covesville)
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- [Visit Blue Ridge Tunnel Trail ](https://www.expedia.ca/Blue-Ridge-Tunnel-Trail.dx847217400490500096)
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- [Visit Roseland ](https://www.expedia.ca/Roseland.dx6361484)
- [Visit Tyro ](https://www.expedia.ca/Tyro.dx3000460704)
- [Visit Waynesboro ](https://www.expedia.ca/Waynesboro.dx6733)

- [Car rental Afton ](https://www.expedia.ca/Car-Rentals-In-Afton.d6056907.Car-Rental-Guide)
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- [Enterprise Rental Cars in Blue Ridge Tunnel Trail ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Blue-Ridge-Tunnel-Trail.d847217400490500096-c15.Car-Rental-Guide-Suppliers)
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- [Things to do in Roseland ](https://www.expedia.ca/Things-To-Do-In-Roseland.d6361484.Travel-Guide-Activities)
- [Things to do in Waynesboro ](https://www.expedia.ca/Things-To-Do-In-Waynesboro.d6733.Travel-Guide-Activities)

- [Book Vacation Homes in Wintergreen on Expedia.com ](https://www.expedia.com/Wintergreen-Private-Vacation-Homes.d10811-aaPrivateVacationHomes.Travel-Guide-Accommodation)