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. - 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.
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Please respect our neighbors! There are year-round residents in the vicinity. Quiet hours are from 10 PM to 8 AM.
No refunds due to weather.
No open fires, except at the propane fire table
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
About the area
Wintergreen
Located in Wintergreen, this holiday home is in the mountains. Zeus Digital Theater and Waynesboro Heritage Museum are cultural highlights, and some of the area's attractions include Wildlife Center of Virginia and War Fields. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain biking nearby.
Bold Rock Hard Cider Nellysford Cidery - 13 min drive - 19.1 km
Shenandoah National Park - 17 min drive - 21.4 km
University of Virginia - 36 min drive - 60.2 km
Monticello - 42 min drive - 68.5 km
Getting around
Staunton Station - 42 min drive
Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 57 min drive
Restaurants
Belties - 19 min drive
Iron & Ale At Wintergreen Resort - 23 min drive
Devils Backbone Brewing Company - 16 min drive
The Market - 4 min drive
The Edge - 5 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 26 Mar, 2026, prices found for a 1-night stay for 2 adults at Upscale and Family-Friendly in Wintergreen on 19 May, 2026 start from S$655, 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).
How much is parking at Upscale and Family-Friendly in Wintergreen?
On-site parking is available at the property.
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 Wintergreen holiday home is located in the mountains, within 1 mi (2 km) of George Washington National Forest and Wintergreen Resort. Raven's Roost Overlook is 3 mi (4.8 km) away.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house was big,comfortable and clean. We appreciated being able to bring our pets too.The hot tub was hot but was a bit dirty. Our family enjoyed the sauna and deck area and had a wonderful stay!
Fantastic Stay! The home was exactly as expected and was perfect for our families. The kids had so much fun in their room and we appreciated how well stocked the kitchen & linens were. We will definitely be back!!
Erica S.
Stayed 2 nights in Feb 2026
Verified
10/10 Excellent
Carroll C.
14 Feb, 2026
Liked: Check-in, communication, listing accuracy
Definitely a 5 star! We had a great stay. The house was perfect for our family, well appointed and comfortable. 15 of us skied 3 full days and the hot tub and Steam room were an added delight! We would certainly stay here again! Thank you
Jennifer was an amazing host. She stayed in touch and was always helpful. The property is beautiful with all the comforts of home. Would definitely recommend.
House was amazing as shown in the photos. Plenty of room for everyone and great layout. Our kids were a little older but loved the upstairs kids lair with the rock wall. Great walking culdesac and quiet neighborhood but just a couple of minutes from the spa and gym, Frost and Fire and the slopes. I don’t want to rent this house again, I want to buy it! Great hosts and great house. Have rented nearly every year and this is the best house yet!
Extended family hiking trip with six adults and two young kids. The house works really well if you want a large common space but also want to give a family privacy with their own space on the lower level. The kids playroom, large dinner table for dinner and cards and hot tub/sauna were a huge hit and used everyday during our stay.
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!
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!
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.
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.
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!
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!
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.
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
About the host
Hosted by New School Hosting
Hello, friends! We are thrilled to welcome you to Sutton’s Roost! Wintergreen is a special place and we thoroughly enjoy the scenery, food, hiking and family-friendly activities. Our kids especially love the gem mining and ninja course at Discovery Ridge. When not at Wintergreen, we are fully immersed in kid activities back in the Richmond area, traveling to our favorite spots and playing with our pack of pets- dogs, a cat, chicken and fish!
Languages:
English
Premier Host
They consistently provide great experiences for their guests