Title: Sherando Condo Rentals from CA $302 | Expedia.ca

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# Search Condos Rentals in Sherando from CA $302

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## Check prices for these dates

Next weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248634999427295&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248634999427295&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248634999427295&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248634999427295&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Sherando condo rentals

![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/e57932c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

### The Modern Mountain Condo 

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

Wintergreen Resort

10/10

Exceptional

(34)

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

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

Kelsey N.

CA $130

CA $319 total

includes taxes & fees

Dec 14 - Dec 15

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

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

![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)

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

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

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

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

Wintergreen Resort

10/10

Exceptional

(92)

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

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

Amanda W.

CA $161

CA $362 total

includes taxes & fees

Dec 14 - Dec 15

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

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

![Outdoor dining](https://images.trvl-media.com/lodging/110000000/109100000/109092800/109092787/232bfb44.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)

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

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

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

Wintergreen Resort

10/10

Exceptional

(24)

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

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

Cassie H.

CA $186

CA $480 total

includes taxes & fees

Dec 13 - Dec 14

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

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

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

![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)

### Wintergreen Condo -Steps to Ski and restaurants

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

Wintergreen Resort

9.8/10

Exceptional

(30)

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

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

Michael L.

CA $157

CA $365 total

includes taxes & fees

Dec 14 - Dec 15

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

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

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

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

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122840000/122831700/122831616/10d4b392.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

CA $93

CA $275 total

includes taxes & fees

Dec 17 - Dec 18

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

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

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

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

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

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

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

Roseland

9.6/10

Exceptional

(142)

"Great stay in Wintergreen!"

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

Pete K.

CA $168

CA $362 total

includes taxes & fees

Dec 14 - Dec 15

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

![Smart TV, fireplace](https://images.trvl-media.com/lodging/44000000/43420000/43414900/43414813/231c3001.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Wintergreen Resort

9.8/10

Exceptional

(123)

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

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

John

CA $148

CA $337 total

includes taxes & fees

Dec 14 - Dec 15

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441921/e029b69d.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/b494e4a4.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)

![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442000/102441921/6624f419.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)

"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 $233

CA $405 total

includes taxes & fees

Dec 14 - Dec 15

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

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95270000/95269300/95269237/d40343ff.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)

### 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

(21)

"Excellent throughout"

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

katherine

CA $165

CA $334 total

includes taxes & fees

Dec 13 - Dec 14

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

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

![Children's area](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442095/c1861718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

### Timbers Studio 46 with Wintergreen Advantage

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

Wintergreen

10/10

Exceptional

(2)

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

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

Madison D.

CA $219

CA $368 total

includes taxes & fees

Dec 13 - Dec 14

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

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/8ed802b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102450000/102442100/102442025/593eaa05.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)

### 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)

"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 $219

CA $368 total

includes taxes & fees

Dec 14 - Dec 15

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

![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)

### 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

(302)

"Great view!!"

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

Suzanne W.

CA $123

CA $302 total

includes taxes & fees

Dec 15 - Dec 16

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

![TV, fireplace](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/c2978783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/189a53c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90240000/90233100/90233005/dfeae95a.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

(32)

"Beautiful property inside and out! Awesome views. "

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

Mandy B.

CA $191

CA $385 total

includes taxes & fees

Dec 14 - Dec 15

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

![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)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/8b8c7238.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/64fdaa18.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

(90)

"Perfect location for our weekend stay! Close to trails and breweries and gorgeous views. Responsive hosts, clean and cozy condo. "

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

Cari B.

CA $150

CA $382 total

includes taxes & fees

Dec 15 - Dec 16

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

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

![Interior](https://images.trvl-media.com/lodging/112000000/111310000/111307900/111307828/fdef2745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

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

Wintergreen Resort

9.4/10

Exceptional

(8)

"Beautiful view!"

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

Serge L.

CA $191

CA $401 total

includes taxes & fees

Dec 14 - Dec 15

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

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/0ca17bc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/ac376d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/a99e93cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120090000/120087400/120087344/ae25bee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy Wintergreen Retreat, Fireplace, Patio, Ski Shuttle, Pet Friendly

[](https://www.expedia.ca/Nellysford-Hotels-Pet-Friendly-3BR3BA-Condo-At-Wintergreen-Resort-Golf-Views-Year-Round-Fun.h120087344.Hotel-Information)

Wintergreen Resort

10/10

Exceptional

(1)

"Awesome just Awesome place. Definitely recommend this place. Very well taken care of and everything you needed all rolled into one place. Thank you so much again and we will definitely be coming back. "

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

Lance B.

CA $225

CA $486 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Nellysford-Hotels-Pet-Friendly-3BR3BA-Condo-At-Wintergreen-Resort-Golf-Views-Year-Round-Fun.h120087344.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/b73ebb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/43bd17c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/c1b55eb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99240000/99231000/99230991/ac8a6741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish-Updated-Central -Walk to Slopes-Dogs OK!

[](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information)

Wintergreen Resort

9.8/10

Exceptional

(28)

"This was a great place for our short weekend getaway! We needed a place we could unplug, and that's exactly what we did reading by the fire, but there was plenty to do if we wanted to! We look forward to staying here again."

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

Richard

CA $268

CA $531 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Nellysford-Hotels-Stylish-Updated-Central-Walk-To-Slopes-Dogs-OK.h99230991.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441732/54e4c59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441732/f2f8cffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441732/9ba6a364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441800/102441732/2e5b6c7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Overlook 43 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Overlook-43-With-Wintergreen-Advantage.h102441732.Hotel-Information)

Wintergreen

10/10

Exceptional

(1)

"Clean, beautiful views, lots to do! "

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

Tara Elizabeth M.

CA $412

CA $684 total

includes taxes & fees

Dec 14 - Dec 15

[](https://www.expedia.ca/Nellysford-Hotels-Overlook-43-With-Wintergreen-Advantage.h102441732.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/103000000/102450000/102441900/102441819/119bea0e.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/103000000/102450000/102441900/102441819/b42da9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102450000/102441900/102441819/d841e912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/103000000/102450000/102441900/102441819/fd972b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Northridge 03 with Wintergreen Advantage

[](https://www.expedia.ca/Nellysford-Hotels-Northridge-03-With-Wintergreen-Advantage.h102441819.Hotel-Information)

Wintergreen

10/10

Exceptional

(1)

"We spent the day brewery hopping and came back to relax. Had so much fun and will be returning to this property. "

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

Courtney A.

CA $371

CA $620 total

includes taxes & fees

Dec 13 - Dec 14

[](https://www.expedia.ca/Nellysford-Hotels-Northridge-03-With-Wintergreen-Advantage.h102441819.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/42c89d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/bd8e69ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/6f8277a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/115000000/114160000/114150300/114150295/974f0f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Overlook 180 degree views w/Peloton!

[](https://www.expedia.ca/Nellysford-Hotels-Overlook-180-Degree-Views-WPeloton.h114150295.Hotel-Information)

Wintergreen Resort

9.4/10

Exceptional

(3)

"Excellent stay. Thank you!"

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

Kimberly B.

CA $245

CA $552 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Nellysford-Hotels-Overlook-180-Degree-Views-WPeloton.h114150295.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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## Top Sherando Hotel Reviews

![Howard Johnson by Wyndham Staunton](https://images.trvl-media.com/lodging/1000000/670000/663700/663617/99b5e75e_y.jpg)

### Howard Johnson by Wyndham Staunton

10/10 Excellent

"Ok"

[](https://expedia.ca/Staunton-Hotels-Howard-Johnson-By-Wyndham-Staunton.h663617.Hotel-Information)

![Days Inn by Wyndham Waynesboro](https://images.trvl-media.com/lodging/1000000/20000/13100/13044/b02f560b_y.jpg)

### Days Inn by Wyndham Waynesboro

10/10 Excellent

"Nice Room and staff."

[](https://expedia.ca/Staunton-Hotels-Days-Inn-By-Wyndham-Waynesboro.h13044.Hotel-Information)

![avid hotel Staunton by IHG](https://images.trvl-media.com/lodging/1000000/20000/17600/17558/3f6256d5_y.jpg)

### avid hotel Staunton by IHG

10/10 Excellent

"Check in went smoothly. Room was clean. Only issue was the the door on the shower unit was loose we attempted to tighten however we were unable to. the next morning the handle came loose we notified front desk staff who would pass the message on to maintenance. as it was Sunday maintenance was not in house, clerk did not convey this and when I returned that evening handle remained broken. Upon check out the following day they took off one of my pet fee charges to compensate me for the inconvenience of the shower. "

[](https://expedia.ca/Staunton-Hotels-Avid-Hotels-Staunton.h17558.Hotel-Information)

![Clarion Pointe Staunton East](https://images.trvl-media.com/lodging/1000000/330000/328900/328834/150e95df_y.jpg)

### Clarion Pointe Staunton East

10/10 Excellent

"Clean room | Great Staff | great Breakfast | Parking"

[](https://expedia.ca/Staunton-Hotels-Quality-Inn-Suites.h328834.Hotel-Information)

![Hotel 24 South](https://images.trvl-media.com/lodging/2000000/1320000/1311400/1311324/76d25ca1_y.jpg)

### Hotel 24 South

10/10 Excellent

"The room was clean and comfortable, and, as always, the staff was friendly and helpful."

[](https://expedia.ca/Staunton-Hotels-Hotel-24-South.h1311324.Hotel-Information)

![Sleep Inn Staunton](https://images.trvl-media.com/lodging/1000000/170000/168400/168389/f334eca9_y.jpg)

### Sleep Inn Staunton

10/10 Excellent

"A very nice hotel, and the perfect area and near tons of food choices. Very clean, renovated and the breakfast was just enough for us. Front desk reception were very helpful and polite. Highly recommend."

[](https://expedia.ca/Staunton-Hotels-Sleep-Inn-Staunton.h168389.Hotel-Information)

![Comfort Inn](https://images.trvl-media.com/lodging/1000000/70000/64100/64084/2a69aac3_y.jpg)

### Comfort Inn

10/10 Excellent

"Front desk and breakfast staffs were very attentive and friendly"

[](https://expedia.ca/Staunton-Hotels-Comfort-Inn.h64084.Hotel-Information)

![Quality Inn Verona - Staunton North](https://images.trvl-media.com/lodging/1000000/180000/172800/172798/a429ddd5_y.jpg)

### Quality Inn Verona - Staunton North

10/10 Excellent

"Room was clean and nice for the price. Staff was kind and free breakfast was stocked with good stuff…even biscuits and gravy! "

[](https://expedia.ca/Staunton-Hotels-Quality-Inn-Verona-Staunton-North.h172798.Hotel-Information)

![Holiday Inn Staunton Conference Center by IHG](https://images.trvl-media.com/lodging/1000000/20000/19200/19125/c184cf6d_y.jpg)

### Holiday Inn Staunton Conference Center by IHG

10/10 Excellent

"The staff at this Holiday Inn were very kind and accommodating. The place was beautiful, if I had to complain about something, id say the shower curtains smelled of mold and the tub was slightly ratty, but the decent beds and view made up for it. Breakfast is paid, so little different than most holiday inns that offer free breakfast, some of the cups were dirty, but all in all, not bad for the price I think."

[](https://expedia.ca/Staunton-Hotels-Holiday-Inn-Staunton-Conference-Center.h19125.Hotel-Information)

## Find out more about Sherando

## Sherando Condo Rentals information

| Number of reviews | 908               |
| ----------------- | ----------------- |
| Accommodation     | 298 Condo Rentals |
| Lowest Price      | CA $302           |
| Highest Price     | CA $684           |

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- [Things to do in Waynesboro ](https://www.expedia.ca/Things-To-Do-In-Waynesboro.d6733.Travel-Guide-Activities)
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