You'll have the entire home to yourself and will only share it with other guests in your party.
Upscale and Family-Friendly in Wintergreen
Welcome to Sutton's Roost, a designer-decorated home in the heart of Wintergreen. A perfect spot for groups or families, this home boasts a hot tub, outdoor cedar sauna, and multiple outdoor seating areas. Inside, there are upscale living rooms upstairs and downstairs, plus a bunk room with a custom log cabin closet, climbing wall, and 65" TV. With 5 bedrooms total, plus a downstairs living room with a pull-out sofa, there's plenty of room for up to 16 guests. Plus, pet friendly!
The house is about a 5 minute drive to the slopes, dining, and everything else Wintergreen has to offer. There's also a fantastic hiking trail with a gorgeous overlook just a few doors down from the house. If you’re willing to venture a bit further, some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the cabin), two sandy-beach-entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries within a 30 minute drive.
The home layout is as follows:
Main level: - Great room with ample seating and working gas log fireplace (super simple to operate) - Kitchen with gas range and everything you need to prepare large meals, and bar seating for 4 - Dining area with table for 10 - BR1: Master bedroom, king bed, ensuite full bathroom - BR2: King bed - Full bathroom in hallway - Upper deck with table seating for 10, propane grill, and lounge area around propane fire table
Lower level: - Additional living room / game room with shuffleboard table, arcade game, 65" TV, and sofa that converts to full bed - BR3: King bed - BR4: Two queens, plus kitchenette with mini-fridge, microwave and Keurig - Full bathroom in hallway - Lower screened-in deck with hot tub, 3-person cedar sauna, and sitting area - Pet-door access from lower deck to fenced-in side yard - Utility room with washer / dryer and an additional full-size refrigerator
Upper level: - BR5: Master bedroom with 2 bunk bed sets (twin over full), 4 closets (3 are themed for kids, including a custom log-cabin closet), and ensuite full bathroom
Other things to note:
- Sutton's Roost is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). We provide some helpful supplies for pet-owners, plus there's a small fenced-in side yard. - We provide our guests $1500 of coverage for accidental damage to the property or its contents. The cost of this coverage is already embedded in the cleaning fee. - Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more. - The large driveway can easily fit 6-7 vehicles. - Wifi is fast with a strong signal throughout the house and decks. Four of the five bedrooms, plus the great room and the downstairs living room, feature a smart TV where you can access all the main streaming services. - We provide a fully stocked coffee bar with multiple coffee drip and Keurig options - Guests can enjoy free community pool access in the summer season (though the HOA rules stipulate no more than 6 guests at a time, and the permitted hours are 2-6pm). - Pack n play, high chair, and board games provided - We do require a separate rental agreement, which we will send a link to e-sign after you book. There are no additional fees beyond those listed here.
Tips for a Happy Hot Tub - Be sure to unclip the hot tub cover before removing it. - Please do not put anything besides people in the hot tub (like mulch or toys). - If the water level doesn’t cover the jets, you can use the hose to add water. Please disconnect the hose when done, especially in cold weather when it could freeze. - Always put the cover on the hot tub when not in use - this keeps the hot tub warm & filled with water. Using the plastic clips helps keep it from blowing off. - For safety reasons, please don’t add chemicals to the hot tub yourself. If the water looks murky or has a smell, let us know, and we'll have our hot tub expert come by to treat it. - Do not drain the hot tub. - There's no need to turn off the hot tub. It may run the jets on low periodically to circulate water through the filter—that’s totally normal. - Use plastic drinkware around the hot tub.
Property manager
New School Hosting
Languages
English
Add dates for prices
Property amenities
Beach
Beach towels
Ski
Close to skiing
Snowboarding nearby
Pool/Spa
Communal pool
Hot tub
Sauna
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Ice maker
Kitchenette
Microwave
Oven
Paper towels
Refrigerator
Spices
Toaster
Dining
Dining table
Bedrooms
5 bedrooms
Bedsheets provided
Bathroom
4 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Fireplace
Living room
Entertainment
Games
Smart TV
Video games
Outdoor areas
Barbecue grill
Firepit
Outdoor furniture
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Welcoming cats and dogs only
4 pets total
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
In the mountains
Things to do
Arcade/game room
Birdwatching nearby
Fishing nearby
Golfing nearby
Hiking/biking trails nearby
Kayaking nearby
Mountain biking nearby
Swimming nearby
Winery tours nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
Unit size: 3,000 square feet
Similar properties
Modern Luxury Mountain Home within Wintergreen Retreat Collection
Modern Luxury Mountain Home within Wintergreen Retreat Collection
You will receive an email from the host with check-in and check-out instructions
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
4 total pets
Children and extra beds
Children are welcome
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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
About the area
Roseland, VA
What's nearby
Wintergreen Resort - 6 min walk - 0.6 km
Raven's Roost Overlook - 3 min drive - 1.4 km
Reids Gap Trailhead - 7 min drive - 6.1 km
Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 19.1 km
Sherando Lake Recreation Area - 22 min drive - 13.9 km
Getting around
Staunton Station - 42 min drive
Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 57 min drive
Restaurants
Bold Rock Nellysford Cidery - 17 min drive
Devils Backbone Brewing Company - 14 min drive
The Market - 4 min drive
The Edge - 4 min drive
Blue Ridge Pig - 17 min drive
Frequently asked questions
Does Upscale and Family-Friendly in Wintergreen have a pool?
Yes, this property has a pool.
How much does it cost to stay at Upscale and Family-Friendly in Wintergreen?
As of 18 July 2025, prices found for a 1-night stay for 2 adults at Upscale and Family-Friendly in Wintergreen on 27 July 2025 start from AU$1,608.62, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Upscale and Family-Friendly in Wintergreen pet-friendly?
Yes, this property allows cats and dogs (limit 4 total).
What time is check-in at Upscale and Family-Friendly in Wintergreen?
Check-in begins at 4:00 PM.
What time is check-out at Upscale and Family-Friendly in Wintergreen?
Checkout is at 10:00 AM.
Where is Upscale and Family-Friendly in Wintergreen located?
This family-friendly Nellysford holiday home is located in the mountains, within a 15-minute walk of George Washington National Forest and Wintergreen Resort. Raven's Roost Overlook is 3 mi (4.8 km) away.
Have a question?
AI iconBeta
Get instant answers with AI powered search of property information and reviews.
Upscale and Family-Friendly in Wintergreen Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travellers 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.More informationOpens in a new window
Rating 10 - Excellent. 18 out of 21 reviews
10 - Excellent
18
Rating 8 - Good. 2 out of 21 reviews
8 - Good
2
Rating 6 - Okay. 1 out of 21 reviews
6 - Okay
1
Rating 4 - Poor. 0 out of 21 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 21 reviews
2 - Terrible
0
9.4/10
Cleanliness
Reviews
10/10
We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!
Verified traveller
Stayed 3 nights in Oct 2024
10/10
We really enjoyed the house. Great location, close to the slopes and plenty of room for our two families to spread out. Thank you!
Frank S.
Stayed 3 nights in Jan 2025
10/10
Had a wonderful stay in Wintergreen! It was off-season, so the area was particularly peaceful. The home was very well stocked, which was important to us as a family that enjoys cooking--high-end appliances, clean/new pots and pans, properly sharp knives, etc. It's also a great home for kids--the top floor bunk bed room was a hit, as was the arcade and shuffleboard table. And it was great to be such a short walk to really nice vistas and trails.
Nathaniel T.
Stayed 3 nights in Mar 2025
10/10
Perfect place to get away. Much nicer than any rentals I've stayed in previously.
Timothy T.
Stayed 2 nights in Dec 2023
10/10
This home was very nice with an open floor plan that worked well for our family. The game room, hot tub, and sauna were bonuses to entertain our teens…and adults as well!
Glenda S.
Stayed 3 nights in Nov 2024
10/10
We had a wonderful stay. The view out of the living room was spectacular and the house had a good layout. We had everything we needed and then some. Kids had a blast! Would definitely stay again!
Heather E.
Stayed 4 nights in Dec 2023
10/10
Lots of room for family of 13! Kids room and downstairs common area were awesome for grandkids. Kitchen was spacious but pots/pans and cooking utensils could be updated. We brought a lot of our own things and I’m glad we did! Bedrooms were spacious. Beds were fairly comfortable. Location was perfect for time at the resort. Would certainly recommend this house for a lovely vacation!
Susan A.
Stayed 3 nights in Jan 2025
10/10
Perfect home for a family gathering!
Kimberly P.
Stayed 7 nights in Nov 2023
10/10
Great House! We very much enjoyed our time there. We will be going back to this one again next year.
Kurt R.
Stayed 3 nights in Jan 2024
10/10
We spent a long weekend here with our family (kids age range 7-13) and had a fantastic time. Property manager responded very quickly to any questions and one minor issue we had with the Wifi going out. Property was well furnished and equipped and very clean. We all loved the basement game room, hot tub, and sauna. Wonderful location on the mountain and great views. Would absolutely recommend and stay here again!
Jen W.
Stayed 3 nights in Nov 2024
10/10
It was very nice. Beautiful home, friendly people
Alysia E.
Stayed 2 nights in Jun 2024
10/10
This house was an excellent fit for our families, especially as we have quite a few kids under 10. We enjoyed the layout, the games and other fun things for the kids, and the hot tub and sauna were clean and relaxing. Best place we've ever stayed at Wintergreen. The owners were very responsive and were able to sort out a lost item with one of our friends after we checked out. Highly recommend.
John S.
Stayed 2 nights in Nov 2024
10/10
We spent five nights, starting on Christmas Eve. We had family ranging from 7 months to 80+.
The house is as advertised, worked well for all ages, offered entertainment and space for all of us. It is very attractive and comfortable.
Beth A.
Stayed 5 nights in Dec 2023
10/10
Sutton's Roost is a great layout for families with younger children. Plenty of places in the home for kids to play independently. Also, hot tub and sauna great for the adults. The main room of the house is large with high ceilings, space for everyone to come together for meals, games, etc. We enjoyed our stay very much.
Lucky P.
Stayed 3 nights in Oct 2023
10/10
This rental was by far one of the best rental experiences we have had. The home is perfectly laid out for a large family and provides everything we needed and more. The screened lower deck with hot tub and sauna was the perfect place to enjoy the rainy weather we had during our trip. We look forward to bringing our entire family to stay in the future.
crystal m.
Stayed 4 nights in Aug 2023
6/10
We arrived from a long car trip with family and friends and were faced with very poor hygiene on the beds. They were dirty, some even had blood and hair marks on them. We had to wash all the bed linens in order to sleep. This was very difficult because we were tired and had children. We simply did not expect this. We spoke to the owner and someone only arrived at 10am with clean bed linens. However, we had already gone to the trouble of receiving us that was not done.
Marcos C.
Stayed 2 nights in Feb 2025
8/10
Had a temporary cleaning crew before we got there. Not enough bath towels which they sent to us. The delivery team didn't knock on the door left them on the porch and it was raining. No kitchen towels. Remote missing in one bedroom and there were some dirty dishes left in game room.
The house was nice and the location was great to get away.
This was our Women's Ministry Retreat.
Charlene S.
Stayed 3 nights in Jun 2024
8/10
Amber B.
Stayed 4 nights in Feb 2025
10/10
We had an amazing stay at Jennifer's home in wintergreen. The house so easy to find and so close to amenities. The living room was huge and we could fit all our friends and family together and have amazing memories. Prompt communication, Plenty of dishes, sparkling clean rooms and bathrooms, plenty of parking, and a cute kids room, I must say this was a complete experience. We wil visit again! Thank you
Nishes B.
Stayed 2 nights in Dec 2024
10/10
This year’s gathering of our ever growing tribe of children, grands and canine landed us as close to the Heavens as possible.
This property was perfectly set up for sleeping arrangements, meal sharing, dog convenience and activities for all ages… the climbing wall was especially popular with our young gymnast and the free-standing video arcade was nostalgically fun for all ages. Of course, being March, the hot tub and sauna got used quite a bit too.
The ultimate lure of this property however, was the closeness to the Heavens. We hiked just yards from the house, soaked up stunning sunsets through the still bare trees and enjoyed a lovely afternoon beside the Rockfish River at a local cidery.
The management was most responsive and patient when we asked a few questions which were CLEARLY laid out on the instruction link…Note to self: assign someone in the group to read instructions throughly and relay to the rest.
Plenty of photos were snapped, offerings of thanks given and expressions of gratitude delivered…what more could be asked for.
PS: Thanks to the owners for being dog and cancellation…some of the terms and dates for cancellation are far too extreme for my liking.
Have already recommended this property.
Virginia M.
Stayed 3 nights in Mar 2024
10/10
We loved the house. We stayed with our family and another family. House was great. Kids (5total) loved the bunk room. Right next to a trail with amazing views. Owner was very responsive.