Entire home
Upscale and Family-Friendly in Wintergreen
Photo gallery for Upscale and Family-Friendly in Wintergreen





Reviews
9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms4 bathroomsSleeps 16278.7 sq m
Popular amenities
Explore the area
Roseland, VA
- Place, Wintergreen Resort6 min walk
- Place, Bold Rock Hard Cider Nellysford Cidery13 min drive
- Place, Shenandoah National Park17 min drive
- Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)48 min drive
Rooms & beds
5 bedrooms (sleeps 16)
Living Room 1
1 Double Sofa Bed
Lower level 2 queens
2 Queen Beds
Lower level king
1 King Bed
Main level king
1 King Bed
Main level master
1 King Bed
Upper level bunk room
2 Single Bunk Beds
4 bathrooms
Lower level hall bath
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Main level hall bath
Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer
Master bathroom
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Upper level bunk room ensuite bathroom
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
Kitchenette
Dining area
About this property
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.
- 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.
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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs and cats (limit 4 total)
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
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.
Roseland, VA
What's nearby
- Wintergreen Resort - 6 min walk - 0.6 km
- 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
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
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.2/10
Cleanliness
9.8/10
Check-in
9.8/10
Communication
9.8/10
Location
9.6/10
Listing accuracy
Reviews
22 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Feb 2026
10/10 Excellent
Bradley P.
11 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Bradley P.
Stayed 4 nights in Dec 2025
10/10 Excellent
Stratton D.
10 December 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stratton D.
Stayed 2 nights in Dec 2025
10/10 Excellent
Becky P.
10 November 2025
Liked: Cleanliness, check-in, communication, listing accuracy
Becky P.
Stayed 3 nights in Nov 2025
10/10 Excellent
Verified traveller
15 November 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent house!
Verified traveller
Stayed 3 nights in Oct 2024
10/10 Excellent
Tammy G.
18 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tammy G.
Stayed 4 nights in Jul 2025
10/10 Excellent
Timothy T.
14 December 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing place
Timothy T.
Stayed 2 nights in Dec 2023
10/10 Excellent
Frank S.
20 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay in Wintergreen
Frank S.
Stayed 3 nights in Jan 2025
10/10 Excellent
Heather E.
5 January 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect family get away!
Heather E.
Stayed 4 nights in Dec 2023
10/10 Excellent
Kimberly P.
13 December 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Thanksgiving
Kimberly P.
Stayed 7 nights in Nov 2023
10/10 Excellent
Kurt R.
31 January 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome Place
Kurt R.
Stayed 3 nights in Jan 2024
10/10 Excellent
Glenda S.
24 November 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family weekend
Glenda S.
Stayed 3 nights in Nov 2024
10/10 Excellent
Alysia E.
16 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely refreshing!
Alysia E.
Stayed 2 nights in Jun 2024
10/10 Excellent
Nathaniel T.
9 April 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful weekend
Nathaniel T.
Stayed 3 nights in Mar 2025
10/10 Excellent
John S.
10 November 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Best place in Wintergreen
John S.
Stayed 2 nights in Nov 2024
10/10 Excellent
Jen W.
11 December 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic experience
Jen W.
Stayed 3 nights in Nov 2024
10/10 Excellent
Susan A.
11 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for family
Susan A.
Stayed 3 nights in Jan 2025
10/10 Excellent
Nishes B.
11 January 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing home for every age
Nishes B.
Stayed 2 nights in Dec 2024
10/10 Excellent
Patrick S.
25 August 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful House with Beautiful Scenery
Patrick S.
Stayed 4 nights in Aug 2023
10/10 Excellent
Beth A.
30 December 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for large family getaways
Beth A.
Stayed 5 nights in Dec 2023
10/10 Excellent
Lucky P.
23 October 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend in the Fall
Lucky P.
Stayed 3 nights in Oct 2023
10/10 Excellent
crystal m.
4 September 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect
crystal m.
Stayed 4 nights in Aug 2023
6/10 Okay
Chelyce B.
21 August 2025
Liked: Check-in, communication
Disliked: Cleanliness, listing accuracy
Chelyce B.
Stayed 3 nights in Aug 2025
10/10 Excellent
Rebecca & Tim B.
27 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Rebecca & Tim B.
Stayed 4 nights in Jul 2025
6/10 Okay
Marcos C.
8 February 2025
Liked: Location
Disliked: Cleanliness
Beds
Marcos C.
Stayed 2 nights in Feb 2025
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
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