Charlottesville, VA (CHO-Charlottesville-Albemarle)
Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
50 min drive
Room options
About the neighborhood
Wintergreen
Chestnut Springs stay.Within a 10-minute walk of this Chestnut Springs vacation home, you'll find Wintergreen Resort and George Washington National Forest. Also, Raven's Roost Overlook is within 3 miles (5 km) and Reids Gap Trailhead is within 6 miles (10 km).
Shenandoah National Park - 16 min drive - 13.1 miles
University of Virginia - 35 min drive - 37.2 miles
John Paul Jones Arena - 38 min drive - 39.1 miles
Monticello - 42 min drive - 42.4 miles
Getting around
Staunton Station - 49 min drive
Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 58 min drive
Restaurants
Belties - 20 min drive
Hill Top Berry Farm & Winery - 23 min drive
Iron & Ale At Wintergreen Resort - 24 min drive
Devils Backbone Brewing Company - 16 min drive
The Market - 4 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
The Fairway Chalet Wintergreen
Welcome to The Fairway Chalet, your perfect mountain retreat nestled in the heart of Wintergreen Resort. Perched alongside pristine golf fairways with breathtaking Blue Ridge Mountain vistas beyond, this thoughtfully appointed chalet offers the ideal blend of comfort, convenience, and natural beauty. Property Highlights Generous Space: 4 bedrooms and 4.5 bathrooms, perfect for families or groups Prime Location: Situated directly on Wintergreen's championship golf course with panoramic fairway and mountain views Spacious Living: Open-concept floor plan perfect for gathering with family and friends Mountain-Modern Décor: Tastefully furnished with cozy mountain charm Outdoor Living: Private deck overlooking the fairway, perfect for morning coffee or evening cocktails Year-Round Comfort: Central heating and air conditioning, plus a stone fireplace for those crisp mountain evenings Amenities Our chalet comes fully equipped with everything you need for a memorable stay: Fully stocked kitchen with pots, pans, baking equipment, and utensils to make family meals High-speed WiFi and smart TV with streaming services Game Room: Exciting ping pong table, air hockey and retro arcade machine for endless entertainment Washer and dryer for your convenience Premium linens and towels Dedicated workspace for remote workers Board games and books for family entertainment Wintergreen Experience When you stay at The Fairway Chalet, you'll have access to all that Wintergreen Resort has to offer: Winter Activities: Skiing, snowboarding, and tubing just minutes away Summer Fun: Championship golf, tennis, hiking trails, and swimming pool Dining & Shopping: Restaurants, cafés, and boutique shops within the resort Natural Beauty: Explore the Blue Ridge Mountains, scenic overlooks, and nearby breweries and wineries Just 1.5 miles from the Mountain Inn, you are just a short drive from all the spring and summer activities Wintergreen has to offer. The Fairway Chalet is also just up the hill from the famous route, Nelson 151 where cideries, wineries and breweries abound. The home is a welcoming and warm space for large families and big enough to accommodate 2 families! Pull your cars into our 2 car garage and unload with ease. A long driveway allows space for additional cars.
The large open floor plan means there is space for all, while maintaining that feeling of being together. The dining room table will comfortably seat 10 and there are 3 additional stools at the counter for keeping the chef company. You can enjoy the outdoors even if it is a rainy day. We have furniture on the screened in porch where you can drink your favorite beverage or read a book. Step out to the deck and grill up your dinner! With a table and four chairs just off the dining room you can eat inside or out. Out on the wrap around deck we have Adirondack chairs and benches to sit around the fire pit and make s’mores or enjoy a glass of wine after dinner. Plug in the twinkle lights and sit back and relax. The kitchen is fully equipped to brew your favorite warm beverage with a Keurig (coffee pods provided), Krups drip coffee maker (with ground coffee), tea pot (with tea bags), gooseneck water kettle and ceramic tea pot. Other appliances for your convenience included a 4-slice toaster, large toaster oven, microwave, electric 4 burner stovetop, oven and stainless steel refrigerator with ice maker. There is plenty of room and counter space to host everyone in the kitchen. On a chilly evening, build a fire in the wood burning 2 story stone fireplace (wood is provided) and stretch out on the sectional sofa big enough for everyone. The 65” smart frame TV is is visible from the living or dining room so you can login to your favorite streaming services. We have unlimited WIFI so everyone can stream on their devices. Need a quick charge? The living room lamps are equipped with USB ports. If you desire to unplug, next to the fireplace are two built in cabinets full of puzzles, board games and a full set of poker chips. On the first level by the two-car garage is the “bear hole” room where you will find a full size retro arcade, ping pong table and air hockey. Ready to rest for the night? Each of the four bedrooms has its own ensuite bathroom. Each bathroom is supplied with shampoo, conditioner and shower gel. No need to bring a hairdryer either, we have 2. Each guest will be given: 1 towel, 1 washcloth and 1 hand towel. All bed linens are provided for your stay, no need to bring a thing! Just off the living room is a ½ bath for your convenience. On the main floor, the king bedroom, with brand new memory foam mattress, has direct access to the large wrap around deck. There is plenty of room to unpack your bags since the bedroom includes a large dresser and his and her closets. The bathroom has a vanity and tub/shower combo. Upstairs there are three more bedrooms. To your left is the large king size room (brand new Casper memory foam mattress) with vaulted ceilings, large dresser, his and her closets, smart TV and ensuite bathroom with jetted tub and separate shower. You can even step out onto your private balcony and sit at the bistro set with your morning coffee and take in the view. Between the other two bedrooms is a fun loft area perfect for the kids or teens to hangout and watch TV or movies and play games. A full-size futon couch can be used as an extra bed. Bedroom three has a queen size bed and private ensuite bathroom with a vanity and tub/shower combo with a bedside lamp to plug in your devices. Unpack your bags into the dresser and large closet. There is lovely view of the golf course from this room. The fourth bedroom is equipped with two twin beds, large dresser, walk-in closet and ensuite bathroom with separate vanity and tub/shower combo. We also provide an extra roll-away memory foam bed, perfect for a kid or tween. If you are traveling with younger children, our home is ready to welcome them too. We will provide a Pack n’ Play, kid sized table and chairs and a booster seat for mealtime. There are even puzzles, and toys for hours of entertainment. Come experience the magic of the mountains at The Fairway Chalet, where unforgettable memories await in every season. Book your stay today and discover why our guests return year after year to this special mountain haven.
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Gravel flooring in public areas
Handrails in stairways
Hardwood flooring in public areas
Thin carpet in public areas
Upper floors accessible by stairs only
Smoking not allowed
Things to do
Arcade/game room
Safety features
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
General
Unit size: 3,064 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25
Check-out
Check-out before 11:00 AM
Contactless check-out available
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Check-out instructions
The host requires you complete the following before checking out:
Load and start the dishwasher
Remove leftover food and drinks and take out the trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Pets
No pets allowed
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.
Property Registration Number 113
Property is also known as
421240
Frequently asked questions
How close is The Fairway Chalet Wintergreen to the airport?
This vacation home is 42.7 mi (58-min drive) away from the Weyers Cave, VA (SHD-Shenandoah Valley Regional) airport, the closest popular airport to the property.
Does The Fairway Chalet Wintergreen have an airport shuttle?
Airport shuttle services are not available at this vacation home.
Does The Fairway Chalet Wintergreen offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at The Fairway Chalet Wintergreen?
No, there is no casino at this vacation home.
What time is check-in at The Fairway Chalet Wintergreen?
Check-in begins at 4:00 PM.
Is there free parking at The Fairway Chalet Wintergreen?
Free parking is not available at this vacation home.
Does The Fairway Chalet Wintergreen have a pool?
This vacation home does not have a pool.
Does The Fairway Chalet Wintergreen have a spa?
There are no spa services available at this vacation home.
How close is The Fairway Chalet Wintergreen to downtown Wintergreen?
This vacation home is 3.9 mi away from Wintergreen.
The Fairway Chalet Wintergreen Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 13 out of 13 reviews
10 - Excellent
13
Rating 8 - Good. 0 out of 13 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 13 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 13 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 13 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Cindy H.
Jan 30, 2026
Liked: Cleanliness
The home was cozy and lovely. The hosts shared all necessary information and everything went smoothly. We had a wonderful time and would definitely stay at The Fairway Chalet again!
Cindy H.
Stayed 3 nights in Jan 2026
10/10 Excellent
Abby E.
Jan 4, 2025
Liked: Cleanliness
Family Ski Trip
Such a welcoming and inviting place to stay! Would absolutely stay here again!Love that each bedroom had a en-suite bath. The game room was such a hit, and the choice of board games was spot on!! The host was so helpful and a great communicator!Was just a short drive to Wintergreen.
Abby E.
Stayed 3 nights in Jan 2025
10/10 Excellent
Linda C.
Oct 20, 2024
Liked: Cleanliness
Absolutely wonderful!
Our family of brothers, sister, and in-laws had planned for a year to go to the NC mountains. Obviously, this was not going to happen. We were blessed to come upon the Fairway Chalet! Stacie is a wonderful host who is outstanding in her communication ! The Chalet was incredibly well-appointed , with so many features to make you feel at home. With 4 bedrooms and 4-1/2 baths, it met ALL our needs. We sat in the back deck with the gas fire pit, enjoying the views and the golfers! Stacie offered so many ideas to enjoy the area! We highly recommend this beautiful home !
Linda C.
Stayed 7 nights in Oct 2024
10/10 Excellent
Kimberly R.
Nov 5, 2023
Liked: Cleanliness
Great getaway
We had the best time at Fairway Chalet. The house was very clean and very well equipped with pots, pans, trashbags, paper towels, toilet paper, etc. You name it, they had it. The host was very helpful and responsive. I would highly recommend. It is high up into the Wintergreen resort. Beautiful scenery, hard on my vans brakes.
Kimberly R.
Stayed 3 nights in Nov 2023
10/10 Excellent
Heather F.
Nov 9, 2022
Liked: Cleanliness
Friends Getaway
What a great weekend! Our stay was for a long weekend - 4 couples. The house was PERFECT! Nice bedrooms with comfy beds, kitchen had everything you could need and more.
Really enjoyed the spacious common areas for games and relaxing. We also loved the deck and firepit, which we used each evening. The host provided lots of great information regarding the area and access to the home was very easy. The location was close to many breweries and wineries.
I have already been looking at the calendar for another opportunity to visit. Would highly recommend this home to anyone visiting the area.
BTW, the host also left a bottle of local cider for us when we arrived- very nice touch!
Thanks again for the opportunity to enjoy your beautiful home!
Heather F.
Heather F.
Stayed 3 nights in Nov 2022
10/10 Excellent
Nilesh P.
Oct 9, 2022
Liked: Cleanliness
family getaway
Very nice home, plenty of space and things to do. We were rained out for a good part of our stay and enjoyed the games, puzzles and ping pong table. Stacie was very responsive with our questions and provided a list of local restaurants and things to do prior to our arrival.
Nilesh P.
Stayed 3 nights in Oct 2022
10/10 Excellent
Meredith W.
Sep 19, 2022
Liked: Cleanliness
Great stay
This home was great for our entire family. We had a big family dinner here and had everything we needed. It’s in a great location right on the golf course and close to one of our favorite trails. Will come back again!
Meredith W.
Stayed 2 nights in Sep 2022
10/10 Excellent
Carl S.
Feb 27, 2022
Liked: Cleanliness
Ski trip getaway
Well stocked, very clean. Convenient to the slopes. Plenty of space.
Carl S.
Stayed 3 nights in Feb 2022
10/10 Excellent
Betsy L.
Feb 22, 2022
Liked: Cleanliness
Lovely winter getaway
Great house for a family, hostess thought of everything, very good communication throughout. We would stay there again!
Betsy L.
Stayed 3 nights in Feb 2022
10/10 Excellent
Zhaoyuan L.
Jan 24, 2022
Liked: Cleanliness
Great weekend getaway!
We really enjoyed our stay at the house. The host is very easy to reach out and quick in respond. As a large group, we could comfortably sleep in the room and futon. The beds are very comfortable. The kitchen has almost all the cooking utensils and supplies we need. There were boardgames and movies to watch on the TV just as how it listed in the description. As a side note, when we arrived, there were no service on our phone, we were unable to access the check in instructions, but you could connect the guest wifi from the outside in order to get connection. You do have to throw the trash by the end of the day, and that’s located about 3-5mins drive near the ski entrance. Overall we highly recommend this house for the ski trip or friends gathering, it’s a short drive to ski, has beautiful view and is spacious! Hopefully we could have a chance to go back!
Zhaoyuan L.
Stayed 3 nights in Jan 2022
10/10 Excellent
Charles S.
Jan 18, 2022
Liked: Cleanliness
Spacious and comfortable.
The home is very spacious and functional. Our group consisted of two adults and six teenagers and at no time did we feel cramped or uncomfortable.
Large, convenient and functional two car garage that protected our vehicles from 12" of snow and allowed easy loading/unloading in protection. The driveway and steps were cleared of snow before noon the following day.
Charles S.
Stayed 3 nights in Jan 2022
10/10 Excellent
Heather S.
Jan 11, 2022
Liked: Cleanliness
Absolutely Beautiful Home!
The home was beautiful, the location was great, the view was beautiful! We could not have enjoyed our stay anymore! Stacie was a wonderful host and communincation was excellent. There were two families in our stay and plenty of room for everyone! We enjoyed the wood burning fireplace throughout our stay. The beds were extrememly comfortable. and you can tell the host takes pride in her home and making her guests feel welcome. The home is warm and cozy, just what you hope for in a mountain home, we would definitely rent this home again.
Heather S.
Stayed 3 nights in Jan 2022
10/10 Excellent
Yvonne G.
Jan 4, 2022
Liked: Cleanliness
A Perfect Family Getaway
Chestnut Springs was the perfect location for our family gathering for 5 days to celebrate New Year’s Eve/Day and enjoy some family time together. The house overlooks a fairway on the Devil’s Knob course and is also convenient to great hiking trails, The layout of the rooms provides a wonderful open space on the main level for being together and two great spots for the kids to hang out, have fun, & make noise away from the adults. The kitchen is very well equipped and spacious. Each bedroom has its own bathroom and the beds are all very comfortable. The rear deck has a gas grille and a gas-fired outdoor fireplace. We pulled up the Adirondack chairs and a bench to enjoy its inviting warmth on a few cool evenings.
The house has a 2-car garage, which we especially appreciated when an unexpected major snow storm dropped 10 inches of snow! Throughout our stay our host, Stacie, stayed in contact with us to ensure our comfort. We loved our stay at Chestnut Springs!