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Upscale and Family-Friendly in Wintergreen

Family-friendly holiday home with sauna and Hot tub

Photo gallery for Upscale and Family-Friendly in Wintergreen

Indoor spa tub
Smart TV, fireplace, video games
Fridge, microwave, oven, stovetop
Exterior
Smart TV, fireplace, video games

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 16279 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
The current price is AU$1,499
includes taxes & fees
7 Jan - 8 Jan 2026

Explore the area

View map
Roseland, VA
  • Place, Wintergreen Resort
    ‪6 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪13 min drive‬
  • Place, Shenandoah National Park
    ‪17 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪48 min drive‬

Room options

About the area

Wintergreen

A family-friendly stay in Wintergreen awaits you at this holiday home. Within steps you'll find George Washington National Forest and Wintergreen Resort within a 15-minute stroll. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 4 bathrooms, a fireplace and a patio. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a Smart TV and a coffee/tea maker are also available. .Enjoy the Hot tub and sauna. Additionally, you'll find laundry facilities, a games room and barbecues. .With a stay at this Wintergreen holiday home, you'll be 30.7 km (19.1 mi) from Shenandoah National Park.
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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

  • Staunton Station - 42 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 57 min drive

Restaurants

  • ‪Belties - ‬19 min drive
  • ‪Devils Backbone Brewing Company - ‬16 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬23 min drive
  • ‪The Market - ‬4 min drive
  • ‪Blue Ridge Pig - ‬17 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.

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.

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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

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

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

Rules

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

Pets

  • Pets are welcome
  • Only dogs and cats are allowed
  • Maximum 4 pets
    • Service animals are exempt from fees.

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
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
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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

Frequently asked questions

Does Upscale and Family-Friendly in Wintergreen have a pool?

Upscale and Family-Friendly in Wintergreen has a pool and a communal pool.

How much does it cost to stay at Upscale and Family-Friendly in Wintergreen?

As of 29 Dec 2025, prices found for a 1-night stay for 2 adults at Upscale and Family-Friendly in Wintergreen on 7 Jan 2026 start from AU$1,499.42, 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.

What luxury perks are available at Upscale and Family-Friendly in Wintergreen?

This property features 1 hot tub, as well as a fireplace and a living room.

What makes Upscale and Family-Friendly in Wintergreen a romantic place to stay?

1 hot tub, fireplaces, and private patios all help set the scene for a sizzling getaway at Upscale and Family-Friendly in Wintergreen.

Is Upscale and Family-Friendly in Wintergreen family-friendly?

You bet! With amenities such as an arcade and laundry facilities, as well as highchairs and children's dinnerware, it's no surprise that Upscale and Family-Friendly in Wintergreen is a winner with our family travellers.

Is there a private hot tub at Upscale and Family-Friendly in Wintergreen?

Yep, there is a hot tub.

Is there a free airport shuttle available at Upscale and Family-Friendly in Wintergreen?

No, Upscale and Family-Friendly in Wintergreen does not offer an airport shuttle service.

What time are check-in & check-out at Upscale and Family-Friendly in Wintergreen?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Upscale and Family-Friendly in Wintergreen Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 23 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 2 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.2/10

Cleanliness

Reviews

10/10 Excellent

Stratton D.

Liked: Cleanliness
A beautiful, well-appointed house. The hot tub and sauna were fantastic. We will definitely come back!
Stayed 2 nights in Dec 2025

10/10 Excellent

Jill B., Lewes DE USA

Liked: Cleanliness
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.
Stayed 4 nights in Nov 2025

10/10 Excellent

Becky P.

Liked: Cleanliness
Clean and plenty of space. Beautiful location although very high in the mtns
Stayed 3 nights in Nov 2025

6/10 Okay

Chelyce B.

Disliked: Cleanliness
Communication was amazing between the host and I but the outside of the house was not as expected like I saw in the pictures. Cobwebs, green moss and leaves all over the outside both upstairs and downstairs, my family and I didn’t have much cleaning supplies available in the house to clean the outside for our kids and for our leisure but we tried to remove the debris as best we can. Apart from that the inside was nice and well kept but the outside needs more attention for guests or at least have an updated picture of the place as it is now so that expectations are met when visiting.
Stayed 3 nights in Aug 2025

10/10 Excellent

Rebecca & Tim B.

Liked: Cleanliness
We had an amazing vacation here at Sutton’s Roost. Home was terrific for us and our kids. Tons of room, well stocked kitchen, hot tub and sauna to calm our aching muscles after hiking all over the place. Upper back porch to relax and eat and watch the stars. Game room for movie nights with giant TV. Huge comfy beds for all. Wintergreen resort and surrounding area is absolutely amazing. We hiked all the hikes they recommended, walked all over Wintergreen, played in multiple waterfalls, did a few cold plunges, ate at the Edge, went to Sherando Lake, thrift shopped in Waynesboro, bought groceries at th IGA and had an absolute blast. Highly recommend. Owners were wonderful. House was super clean, well stocked and exceeded every bit of our expectations. I’m currently doing research to see if i can get that same couch for my own house because it was so comfy!!! If I could give it 10 stars I would. Wish we could have stayed longer. We will be back!!
Stayed 4 nights in Jul 2025

10/10 Excellent

Tammy G.

Liked: Cleanliness
Well appointed house and property, lots of space, all amenities included. Comms with host were timely and responsive.
Stayed 4 nights in Jul 2025

10/10 Excellent

Nathaniel T.

Liked: Cleanliness

Peaceful weekend

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.
Stayed 3 nights in Mar 2025

8/10 Good

Amber B.

Liked: Cleanliness
Stayed 4 nights in Feb 2025

6/10 Okay

Marcos C.

Disliked: Cleanliness

Beds

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.
Stayed 2 nights in Feb 2025

10/10 Excellent

Frank S.

Liked: Cleanliness

Great Stay in Wintergreen

We really enjoyed the house. Great location, close to the slopes and plenty of room for our two families to spread out. Thank you!
Stayed 3 nights in Jan 2025

10/10 Excellent

Nishes B.

Liked: Cleanliness

Amazing home for every age

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
Stayed 2 nights in Dec 2024

10/10 Excellent

Susan A.

Liked: Cleanliness

Great house for family

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!
Stayed 3 nights in Jan 2025

10/10 Excellent

Jen W.

Liked: Cleanliness

Fantastic experience

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!
Stayed 3 nights in Nov 2024

10/10 Excellent

Glenda S.

Liked: Cleanliness

Family weekend

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!
Stayed 3 nights in Nov 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness

Excellent house!

We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!
Stayed 3 nights in Oct 2024

10/10 Excellent

John S., Richmond, VA

Liked: Cleanliness

Best place in Wintergreen

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.
Stayed 2 nights in Nov 2024

8/10 Good

Charlene S.

Liked: Cleanliness

mostly good

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.
Stayed 3 nights in Jun 2024

10/10 Excellent

Alysia E.

Liked: Cleanliness

Absolutely refreshing!

It was very nice. Beautiful home, friendly people
Stayed 2 nights in Jun 2024

10/10 Excellent

Virginia M., Virginia Beach, Virginia

Liked: Cleanliness

Close to the Heavens

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.
Stayed 3 nights in Mar 2024

10/10 Excellent

Kurt R.

Liked: Cleanliness

Awesome Place

Great House! We very much enjoyed our time there. We will be going back to this one again next year.
Stayed 3 nights in Jan 2024

10/10 Excellent

Heather E.

Liked: Cleanliness

Perfect family get away!

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!
Stayed 4 nights in Dec 2023

10/10 Excellent

Beth A.

Liked: Cleanliness

Great for large family getaways

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.
Stayed 5 nights in Dec 2023

10/10 Excellent

Timothy T.

Liked: Cleanliness

Amazing place

Perfect place to get away. Much nicer than any rentals I've stayed in previously.
Stayed 2 nights in Dec 2023

10/10 Excellent

Kimberly P.

Liked: Cleanliness

Family Thanksgiving

Perfect home for a family gathering!
Stayed 7 nights in Nov 2023

10/10 Excellent

Lucky P.

Liked: Cleanliness

Weekend in the Fall

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.
Stayed 3 nights in Oct 2023