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Modern Luxury Mountain Home within Wintergreen Retreat Collection

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Luxurious Wintergreen Home with gorgeous wall of windows on main level.
Lots of outdoor entertaining space!
Window to majestic Shenandoah Valley Views!
Living area
View of the mountains between the trees in the back deck!

Reviews

9.8 out of 10
Exceptional
5 bedrooms3+ bathroomsSleeps 184200 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Rooms & beds

5 bedrooms (sleeps 18)

Lower Level - Bedroom

+1
1 Double Bed, 3 Twin Beds and 1 Queen Bed

Lower Level - Master Bedroom

1 King Bed

Main Floor - Master Bedroom

1 King Bed

Upper Level - Bedroom 1

1 Queen Bed and 1 Twin Bed

Upper Level - Bedroom 2

2 Queen Beds

3 bathrooms, 2 half bathrooms

Lower Level - Half Bath

Toilet

Lower Level - Master Bath

Bathtub or shower · Bathtub · Toilet · Shower only

Main Level - Half Bath

Toilet

Main Level - Master Bath

Bathtub or shower · Bathtub · Toilet · Shower only

Upper Level - Bathroom 3

Bathtub or shower · Bathtub · Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Dining area

About this property

Modern Luxury Mountain Home within Wintergreen Retreat Collection

With gorgeous mountain views of the Blue Ridge and Blackrock Village this luxury mountain home is one of the largest in the Wintergreen Retreat Luxury Home collection. Featuring 5 bedrooms, 3 full baths, and 2 half baths. The level drive and one step access into the main level allows for easy access. Once inside you will be impressed with the gracious open floor plan and spacious rooms throughout.

The main level master bedroom suite is great for family members with limited mobility. The home also features a backup generator and advanced water conditioning system for our guests comfort and convenience.

The main level includes the soaring, light filled Great Room with cathedral ceiling & stone fireplace, large eat in kitchen with granite, handsome cabinets, tile floors & beautiful master suite with steam shower. Upstairs includes 2 guest bedrooms with multiple sleeping options, full bath and loft with a desk.

The lower level allows for more activities in an additional family room with fireplace, a master suite with full bath, a separate bedroom with a large sleeping capacity, and a half bath. Beautifully maintained and tastefully furnished so you can just walk in and begin enjoying your new Wintergreen vacation!

Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Please return all keys to lockbox
Make sure to take any fireplace ashes to the trash
Broom clean and wipe down countertop surfaces. Also make sure linens are brought to the laundry.
Failure to complete these may result in a negative review from the host.

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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock

About the neighborhood

Wintergreen

Located in Chestnut Springs, a neighborhood in Wintergreen, this vacation home is in a rural area and in the mountains. Wintergreen Resort and Sherando Lake Recreation Area are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Shenandoah National Park and Rockfish Gap Entrance Shenandoah. Wildlife Center of Virginia and War Fields are also worth visiting. Kayaking and rafting offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
View more Vacation Homes in WintergreenOpens in a new window
Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.1 km
  • Shenandoah National Park - 17 min drive - 21.8 km
  • University of Virginia - 36 min drive - 60.6 km
  • Downtown Mall - 40 min drive - 66.0 km
  • Monticello - 43 min drive - 68.9 km

Getting around

  • Staunton Station - 42 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 63 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 - ‬17 min drive
  • ‪The Market - ‬5 min drive

Frequently asked questions

Does Modern Luxury Mountain Home within Wintergreen Retreat Collection have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

How much does it cost to stay at Modern Luxury Mountain Home within Wintergreen Retreat Collection ?

As of Mar 25, 2026, prices found for a 1-night stay for 2 adults at Modern Luxury Mountain Home within Wintergreen Retreat Collection on Apr 19, 2026 start from $437, 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 Modern Luxury Mountain Home within Wintergreen Retreat Collection pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Modern Luxury Mountain Home within Wintergreen Retreat Collection ?

Check-in begins at 4:00 PM.

What time is check-out at Modern Luxury Mountain Home within Wintergreen Retreat Collection ?

Check-out is at 10:00 AM.

Where is Modern Luxury Mountain Home within Wintergreen Retreat Collection located?

Located in Chestnut Springs, this vacation home is steps from Wintergreen Resort and George Washington National Forest. Raven's Roost Overlook is 2.9 mi (4.7 km) away.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 51 out of 56 reviews
Rating 8 - Good. 4 out of 56 reviews
Rating 6 - Okay. 0 out of 56 reviews
Rating 4 - Poor. 0 out of 56 reviews
Rating 2 - Terrible. 1 out of 56 reviews

9.6/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Karen N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay for a large group. Clean and excellent location.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Terri B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time. Our host was great to work with and the house is large enough for us, our 3 kids plus spouse and 6 kids. The kitchen is outfitted for the chef in the family. We will visit again.
Stayed 4 nights in Jan 2026
Verified

10/10 Excellent

Jessica B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful getaway!!

Perfect place to relax and enjoy the company of friends and family.
Stayed 4 nights in Apr 2025
Verified

10/10 Excellent

Sandra A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is well appointed and has a gorgeous view from the deck. The location is great and is really close to a wide range of breweries, cideries and wineries!
Stayed 2 nights in Aug 2025
Verified

8/10 Good

Ron P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Well appointed kitchen-gas grill did not have gas. House was clean. Host was responsive to questions and deficiencies(propane gas empty)Beautiful sunrises/sunsets!
View from main floor deck
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Tara P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home for a fun weekend!

We loved our stay for a weekend visiting wineries and breweries. It was a great home!
Stayed 3 nights in Nov 2023
Verified

8/10 Good

Janet S.

Liked: Check-in, communication, location, listing accuracy

Family apple picking

Property was very nice and a great location!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Lainey F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

So great!!

Perfect amount of space for our group
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Lynn F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kitchen was very well equippedIt isn’t ski season
Gorgeous sunrose
Family fun
First fire of the season
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Christine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home!

Wonderful ski trip and great views
Stayed 3 nights in Feb 2022
Verified

10/10 Excellent

Linda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

This VRBO was well stocked and spacious.

This is a beautiful property. The manager was very responsive to any questions.
Stayed 3 nights in Dec 2024
Verified

10/10 Excellent

mike q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ski Trip

Great property with excellent sunrise views.
Stayed 3 nights in Feb 2024
Verified

10/10 Excellent

Libby C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

ski vacation

Kitchen was well stocked. Owner was responsive about keyboard. House and beds were comfortable.
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Becky B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our group

Clean house lots room to play games and bedrooms more than adequate
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

Mary P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

lovely, comfortable weekend stay

The house was clean and well-appointed. All 12 of us had comfortable beds, and loved the balconies & decks around the house. Nathan, the host was accommodating and easy to deal with. Can't wait to come back!
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Joan P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at Chestnut Springs

Really enjoyed our time at this lovely home in Wintergreen. It met our expectations in every way--beautiful house and view, fully equipped kitchen for cooking for a large family, very spacious rooms. We particularly appreciated the host's accessibility for questions and readiness to help.
Stayed 3 nights in Jan 2023
Verified

10/10 Excellent

Lisa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Scenery and Home With Nice Touches

We gathered as old friends and were able to catch up on the expansive deck with a breathtaking view. The living room and kitchen were also the perfect size for our gathering of 8 adults. The kitchen was well outfitted with upgraded extras. We would love to visit again!
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Bill L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for a milestone birthday!

As described, spacious, and generously supplied with everything needed for our large group aged 2 years to 80! Loved the mature hardwood forest ambiance with birds, bears (nearby) and even a bobcat! Thanks and hope we can return someday soon.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Deanna R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great ski weekend

We enjoyed a wonderful weekend with friends. At Wintergreen Retreat. It was a beautiful home with lots of bedroom space and easy to get to everything nearby. Thanks for everything!
Stayed 4 nights in Jan 2023
Verified

10/10 Excellent

Janae N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip in the mountains

My family and I stayed at this property and it was perfect for our occasion! The home is beautiful, spacious, and has amazing views in the mountains. Everything was very clean and the home had everything we needed. The host was responsive and accommodating with a late check out that gave us more time for a morning brunch before leaving :) thanks for the great trip!
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Thomas F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was very clean and entry was easy once we found the lock box. The open floor plan was especially nice for our family group of 10. All the bedrooms were large and beds were comfortable. The kitchen appliances were new and all worked well. The kitchen was very well stocked with small appliances, dishes, flatware, cookware, and spices. We really enjoyed the large deck with a view. We ate every meal alfresco! It was a memorable July 4th weekend for the entire family!
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Olivia H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

It was all that!!

The home and community was exactly as it was advertised!! My family enjoyed all the amenities. We were impressed by the comfort of the beds! Had everything in the kitchen you needed and more! I recommend this house everytime
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Lynn C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Multi-family ski weekend

Spacious home that worked well for our group of 15. Having a separate hangout area for the teenagers was a big bonus. Nice, flat parking with a short drive down to the slopes. Functional kitchen with plenty of plates and silverware for all the guests. Only wished for a few more hooks to hang up everyone’s ski gear.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Mary K P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

13 people stayed the weekend

It was great again. This is our 3rd or 4th year. A few items needing repair on the deck and the door leading to it.Very comfortable and well equipped kitchen and bathrooms.
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Rosanna W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Harry Potter Weekend with Hurricane Helene!

Awesome place to wait out Hurricane Helene! And oh the views after the fog lifted! This house was the perfect distance for Staunton’s Queen City Mischief and Magic weekend! Plenty of vineyards, breweries, and a few yummy places to eat. I do recommending bringing all your planned meals up with you as shopping is not real close. We will def be coming back!
Stayed 3 nights in Sep 2024

About the host

Hosted by Nathan Van Orden

Host profile image
The owners purchased Chestnut at Wintergreen Resort in 2020 to provide an option for multiple families to rent a larger house within the Wintergreen Retreat collection of homes. We hope other families will enjoy this latest addition and appreciate our attention to detail as we strive to make your vacation on the mountain as enjoyable as possible.

Why they chose this property

The owners chose Wintergreen they grew up with a family home on the mountain. They enjoy the four seasons resort with hiking, fishing, skiing and year around activities. They also enjoy being near the Virginia Horse Center and the variety of horse activities close to Wintergreen. They find the central location ideal for day trips within the region.



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