
Vacation rentals in Wintergreen Resort
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Top-rated vacation rentals in Wintergreen Resort
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Other great vacation rentals in Wintergreen Resort
Guest favourite

Home in Wintergreen Resort
4.88 out of 5 average rating, 17 reviewsBluebird Mtn Home ~Dog Friendly ~ ~No step entry~
WhitneyRating, 5 stars2 days ago
John’s mountain home was absolutely perfect. He easily approved a late check out to accommodate my son’s nap, he proactively let me know when the house was ready early, and he quickly addressed questions we had once we were in. The home was clean and inviting throughout. The attention paid to dog-friendliness was above and beyond! They had dog beds in a couple rooms and toys for pups to play with. The location is great, too. A quick drive to a few spots at the resort and 15/20 mins to some great breweries and wineries where my son and dog could play. I would definitely stay at John’s house again!
Guest favourite

Home in Amherst
5 out of 5 average rating, 8 reviewsCountry home with amazing views
KatherineRating, 5 stars8 months ago
It was beautiful and peaceful. The house was clean and spacious and if he had any questions or needed help with something she was very responsive. It was a healing trip for our family and exactly what we needed. We hope we can return next year!
Guest favourite

Home in Wintergreen Resort
4.85 out of 5 average rating, 131 reviewsGrand Chalet w/ Hot Tub - Near Wintergreen Resort
KathrynRating, 5 stars2 weeks ago
We stayed at this mountain retreat for my mom's 70th birthday and could not have been more satisfied with the home! Everything in the house is updated and of great quality. The views are spectacular and can be taken in from one of three porches, all of which contain comfortable seating. The kitchen was a highlight for our group as we cooked special meals for the birthday party. It is stocked with everything you could possibly need. The hosts include many items like spices, condiments, paper plates, oils, etc., which is a lovely touch considering that it is a trek to the grocery store. You can tell that the hosts approach their rental with a spirit of generosity and put guests first. Towels, blankets, extra pillows, and truly anything you might need or want were provided. The location is very close to several trailheads; a couple are within a short walking distance. The home is also a great launching point for other attractions in the area. We hope to be back!

Home in Nellysford
5 out of 5 average rating, 4 reviewsSpring Break:Hiking, Breweries, Wineries
EileenRating, 5 stars4 months ago
Gretchen was so friendly and welcoming! I loved that they had a doggie room, which my dog absolutely loved. She would hang in there on the bed after being outside. The house was so cute and quaint and Gretchen was so personable, helpful and accommodating. The location was perfect. My mother and I had a lovely Christmas Eve dinner at Three Notch'd Craft Kitchen which was like a 5 min walk away from the house, hiking was a short drive, as was plenty of other good restaurants, wineries, breweries, and grocery shopping. Can't recommend enough!
Guest favourite

Home in Waynesboro
4.83 out of 5 average rating, 23 reviewsModern 5BR Home | Spacious Getaway in the Valley
MichaelRating, 5 stars5 months ago
There is a ton of space in Arturo's place, two full baths and two halfs, and plenty of beds. Well decorated and well lit. Great TV/Multi-media. It was perfect for a large group. We would definitely rent again.
Top guest favourite

Cabin in Montebello
5 out of 5 average rating, 25 reviewsBlue Ridge Cabin 5
KatieRating, 5 stars4 months ago
Spent New Year's with my husband and two Yorkies nestled deep in the woods, and it was everything I hoped for—and more! The property is surrounded by towering trees, offering a sense of tranquility and seclusion that's hard to come by. The bed deserves a special mention— it was the most comfortable bed I’ve ever slept in! We spent all three days hiking some of the best trails and relaxed comfortably watching TV in the evenings with a nice glass of Malbec. If you're looking for a peaceful retreat where you can reconnect with nature without sacrificing comfort, this Airbnb is the perfect choice. I’ll definitely be returning! Thank you Jerry and Chris.
Superhost

Cabin in Wintergreen Resort
4.87 out of 5 average rating, 79 reviewsDog Friendly - Backs to Golf - Spacious Deck
JillRating, 5 stars2 months ago
Pip's place is close enough to all the features that Wintergreen Resort offers to make them easily accessible, but far enough away to give you space and quiet. It backs up to the golf course so the back has a lovely setting. We were especially grateful that the place is dog friendly. We would totally recommend this spot and would stay again in the future.

Condo in Wintergreen Resort
4.92 out of 5 average rating, 84 reviewsCondo on Eagles Swoop! Slopes outside your door!
LoriRating, 5 stars2 months ago
This place is FANTASTIC! It was cozy and more spacious than most slope side condos. It was perfect for a weekend trip to skiing for our family of 5. Bunk beds room for kids. It has a place to store skis in a closet outside the condo. Steps from parking lot up a few stairs to condo. Beautiful to sit on the porch and watch skiers go down Eagle Swoop Slope. Easy access to the whole mountain from here. Night skiing which allows you to ski all day and night and get back home (which is not the case for all slope side places at Wintergreen). We had a blast. The place was well stocked with essentials, firewood right outside, lots of games. We will be back. Wintergreen has lots of year round activities and this place is located right in the heart…super close to the market gas station and the main Wintergreen resort. 10/10 recommend!
Quick stats about vacation rentals in Wintergreen Resort
Total rentals
670 properties
Nightly prices starting at
$97 CAD before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
520 properties are a good fit for families
Pet-friendly rentals
220 properties allow pets
Rentals with a pool
420 properties have a pool
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