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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Guest Swimming Pool - Outdoor, Heated, Pavillion, Very close by

Bedrooms 5
Half Baths2
Space 2,567 sq. ft.
Property type house
Minimum Stay 3 - 4 nights


About the property

SPACIOUS INDOOR AND OUTDOOR SPACE - 4000 square feet - Ping Pong for rainy days

Hello Travelers, Adventure Lovers,

If you haven’t been to the Wintergreen Resort area recently or haven’t been here during the “other” 3 seasons, then read on to come to see nature, mountains, wildlife, flowers, trees, and magnificent views at every turn.

As children grow and vacations change, awesome 2nd homes aren’t being used by the HomeOwners and they want to share them with you. Personal belongings have been removed and the homes that we manage have been beautified and upgraded to be the best they can be for you, our Guests. In between Guests, the home is meticulously cleaned and Approved Pets are Welcome

Growing fast is the Nelson 151 LOVE THE ROAD and surrounding Blue Ridge Playground. It isn’t a rural road to the mountains anymore.

This lovely and inviting historic Rockfish Valley has found its calling. A few of its best features are: The National Forest, Rivers, Lakes, Walking, Hiking, Fishing, Orchards, Great Food, Picnics, Wine Tasting, Craft Brews, Distillery, Ciders, Natural Hops Growing, Vineyards, Tours, Excursions, Golf, Bicycling, Antique Shopping, Historic Homes, Wildlife, Adventure Horseback Riding,

#1 on the list of features for Adult and Kid visitors is GOOD FOOD. The Chef's kitchen at Chestnut Place Memories Guest Home is well-equipped, stocked with everything you need but the food and drink to make fantastic meals. The propane grill is always waiting. Eat outside on the deck in the sun or shade under the forest trees and the views or eat inside near the kitchen or by the sliding glass doors and cathedral ceilings. What could be better than sitting outdoors with family and friends and kids sitting outside telling each other stories, finding those “teachable” moments. The deck at Chestnut has a chiminea and stacked for those cool mountain evenings, there is something so natural about building a fire, sitting around it and talking or roasting marshmallows or making S’Mores.

To pick up Groceries on your way in to the Blue Ridge Playground Wegmans in Charlottesville is the best grocery store we have ever been to. Oh my, you just can’t believe the food. I would say order online, but no, you need to go in and look at this food. Steaks, Salmon, prepared meals, anything you can think of prepared 20 different ways will be at your finger tips.

If you want to order good food online and let the Grocery Store put it in your car, then call Harris Teeter in the Blue Ridge Shopping Center at Crozet.

And how important is a good restaurant? Treat yourself to a stop and eat good food prepared by a good Chef. Vacationers and visitors go places with good food, and we think that the Wild Wolf Brewery in Nellysford on the way to the Chestnut home has the best. They have a Chef that has been there 5 years and the menu items sound and look good and are so delicious. They also have a courtyard that is Pet Friendly.

Also with great food is the Devil’s Backbone Basecamp Brewputb & Meadows. Not just one Restaurant, but indoor and outdoor eating (some pet friendly). about one year ago Devil’s Backbone was acquired by Anheuser-Busch and the food although good before is now great. They have taken that awesome area and have organized and grown the space. The Summit Restaurant (a relocated and local Arrington reconstructed train depot from 1870) serves breakfast from 7 to noon. DB also have a functioning catering-kitchen and it is a great place to host wedding events, corporate meetings, family get-togethers and more. Love the “Tastings”. We have more recommendations for you.

These mountains have it all. The home is beautiful, and comfortable with indoor, outdoor and rainy day space.

Windows and blinds throughout with sliding glass doors to two large wrap around decks. Soak up the sun and shade.

Hiking is everywhere. 30 pristine miles at the Resort maintained by the Nature Foundation, with the Blue Ridge Parkway, Skyline Drive, Appalachian Trail and Sherando Lake just a few minutes away.

Try something new. The wine-making in this area is fast becoming the Napa Valley of the East. Try the newest way to make wine a part of your life. Local tasting rooms are popping up everywhere here. Make a quick stop by and taste or have a glass of wine and enjoy the mountain views. If you prefer, taste and select a bottle of wine to go with your dinner.

For example, Flying Fox has a nice tasting indoor and outdoor space right off Route 15. Select a Flying Fox or other local wine from the Wild Wolf Brewery menu.

Make romance, soak up the history and adventure in one of Virginia's best kept secrets. Make awesome memories with family, kids, and friends, and avoid the crowds. Relax when you can, watch movies or sports on the best cable channels, best reception and high-speed wi-fi.

Guests check out and I ask: How was everything? This is what I hear: "Everyone loved the home.” Please check out the 38 straight 5 star Reviews on this Chestnut Place home.

The Family Room is also a Game Room/Toy Room with a wide screen TV, gas fireplace, games, movies, comfortable furniture, sliding glass doors and a Ping Pong Table.

The Chestnut Place Memories home is a spacious, executive/family friendly home that has 3 unique levels with 3 Master Bedrooms. There are 5 bedrooms, 3 full baths, and 2 half baths making up 4000 square feet of living space. Two levels with wrap around decks add to the outdoor living space in the forest. Pack your bags, bring your personal items and groceries, the home is stocked with everything else you will need to run the home and extras.

Ask about our Summer, Fall, Winter, and Spring Vacation Specials that include a stay for 7 days, yet only pay for 5 days at The Chestnut Place Memories Home.

Make the most of your days off. We offer and encourage early check-ins and late check-outs whenever possible.

Come and make forever memories with your family and friends at the Chestnut Place Memories Home.

Three Levels, a living room on one, a family/game room on another. Fireplaces (1 gas and 1 wood-burning) with sliding glass doors onto 2 huge decks that wrap around the house. Each of the three levels has a Master bedroom and full bathroom. Easy access for anyone through the front door and the main floor with Master bedroom, full bath, and deck.

This open, spacious home with awesome hardwood floors is ideal for 1 or more families vacationing together with plenty of get together space and individual privacy. TVs are setup with high-end Nelson Cable and movies. High speed internet. A large TV in the living room, the family room and each Master Bedroom on the 1st and 2nd floor.

The third floor has a Master bedroom with a Queen bed, skylights and side chair. The third floor extra Guest bedroom has a Queen bed, a twin bed, and a crib with a large closet. Extra cots can be provided with an early request.

We offer extras:

If you would like us to US mail you a package of local brochures, please call us or email us to the Host contact information provided here on this site. We can send you information about activities and/or more places to Eat and/or Wineries, Breweries, Ciders, Distilleries. Just describe what you would like us to send you.

If you would like to consider us to make up a BackPack(s) for your hike with hiking necessities, food, drinks, please call or email us to the Host contact information.

Thank you.

Karen and Ken Barber

Vacation Rentals At Wintergreen Resort

More Details

Property Manager
Ken and Karen Barber
Member since: 2003
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
August 13, 2017

About Ken and Karen Barber

About Us: We, Ken and Karen Barber of Vacation Rentals At Wintergreen Resort are the Guest Experience and Vacation Property Managers for The Chestnut Place Memories Guest Home (602015), The Black Bear Mountain Retreat (928714), and The TreeTop Flyer Guest Home (795870). The Chestnut Place Memories Guest Home is owned by a working Mom and Dad and kids. Although the owners built this home for the family, the kids are now grown. They put their heart and souls into designing and building this beautiful and comfortable mountain home. Rather than let her go, they have decided to let us manage and share the home, the Resort and the area with weekend and vacationing Guests.

We worked and raised our children mostly in Richmond, Virginia, always making time to come to this beautiful Blue Ridge Playground. Ken is still active on the National Ski Patrol , going on about 30 years now. Ken and Karen are both PSIA Certified Ski Instructors, hikers, campers and Licensed Coast Guard Captains. For several seasons we chartered sailboats Windancer and Proud Mary, taking Guests out on the water in the Northern Neck of Virginia and the Chesapeake Bay.

Virginia Is For Lovers.

We believe that Wintergreen Resort and The Blue Ridge Playground is a best kept secret. A secret for families and friends to enjoy every season of the year. Whether it be ski/ride or Guided Hikes or Guided Fly Fishing or Adventure Horseback riding or Native American History & more, we will help arrange any activity that you love or want to experience. It is time and we are trying to let the secret out.

Please follow us on social media or our website for all the current activities or news in the area.

Why Ken and Karen Barber chose Virginia

Why This Property? Check the Reviews. Previous Guests say it best. Sitting on the side of a mountain is what you would expect and get. Long, wrap around decks, floor to ceiling windows overlooking the forest and ski slopes on the distant mountain take your breath away. A base camp where you can renew your resources, ever important place to eat, to sleep, to rest in between all the things that you want to do, or hide and enjoy from a distance.

We love and try to do everything possible for Guests to enjoy the home and area. The Guests reward us with returning year after year and writing those treasured Reviews.

Nestled in the George Washington Forest, with wildflowers all around in a relatively flat area, choose this property because it is has so much light, shared and private space, is modern, and easily accommodates one to three or more families or group easily for group get-togethers, reunions, wedding preparation or individual privacy when needed.

Bring your bike or walk for great exercise and easy or difficult trails. It is .4 mile to the Chestnut Summer Heated Outdoor POOL open from Memorial Day to Labor Day. The pool is in a wooded area with Life Guards, a large pavilion, seating and grill. Wintergreen Resort is unusually cool in the summer with lots of sun, but lots of shade and a breeze. Normally 10-12 degrees cooler than the Valley, thus the heated pool.

This home is filled with windows, cathedral ceilings, hardwood floors, except the kitchen tile. The kitchen is modern and there is a new gas grill on the deck. Easy parking.

Each floor has a Master bedroom. Floors 1 and 2 have two side by side sliding glass doors onto large covered wrap around decks. Floors 1 and 2 have Master Bedrooms with full baths and a 1/2 bath for the other bedroom on that floor. Floor 3 has a Master Bedroom, a full bath and an extra bedroom with a Queen bed, a twin bed and a crib. Each bedroom is quite large and each could accommodate an extra cot.

What makes this house unique

Unique Benefits include passes and close proximity to the summer-time pool, the Shamokin Nature Preserve, the Nature Foundation, the Post Office, the Spa, and a dog park. This home is on the Mountaintop part of Wintergreen, near Sherando Lake (a National Park), the Blue Ridge Parkway and The Skyline Drive, but the Valley and remaining Blue Ridge Playground has so much to offer.

Plan your vacation and take advantage of the incentive:

"Pay for 5 days but Stay for 7. There is so much to do in the Blue Ridge Playground."

Although this is a popular home and booked frequently, check back on a Thursday. If she is not booked for that upcoming weekend, please ask for the Special Getaway incentive:

"Stay for 2, Pay for 1 and part of a Cleaning Fee of $145."

Pack your bags with personal items and groceries. Paper towels, trash bags, dishwashing detergent, soaps, aluminum foil, and spices are a few of the items included with the home. We have stocked the home with everything you will need to have a grand time. If you want to order your groceries and pick them up on the way, just ask and we will help you with this Harris Teeter special offer.

Wintergreen Resort, Rockfish Valley, Monticello, and area activities and calendar of events and more are bookmarked on our website.

Thank you for looking at our listing. Please inquire through this site or call if you have questions about booking or activities or the area.

We thank VRBO and HomeAway for promoting and advertising this property. We support and honor the Service Fee for each inquiry through this website.

We welcome you, your family, your friends, and your pets to this lovely, spacious, bright and warm and meticulously and sparkling clean home in the heart of Wintergreen Resort, in the heart of The Blue Ridge Playground.

A base camp place to make memories lasting a life time.

Thank you. Questions? Please call or write.

Ken and Karen Barber

Guest Experience and Vacation Property Managers


Wintergreen Resort House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
Floor Area:
  • 2567 sq. ft.
House Rules:
  • Check-in: 4:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 16
  • Minimum Age Limit for Renters ...
  • pets considered ...
  • Events Allowed
  • children welcome
  • non smoking only
Location Type:
  • Downtown ...
  • Golf Course View ...
  • Mountain View ...
  • Resort
  • Rural ...
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine ...
  • Wood Stove ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 3 Bathrooms
  • 2 Half Baths
  • 2nd Floor (Main) Floor Bathroom in Hall - toilet , Pedestal sink, mirror
    1st Floor Master Bathroom - toilet , combination tub/shower , Mirror, sink, and dressing area outside bath; linen closet
    2nd Floor (Main) Master Bathroom - toilet , combination tub/shower , Mirror, sink, and dressing area, STEAM BATH!, Linen closet
    1st Floor Bathroom in Hall - toilet , Mirror, sink, vanity, counter top
    3rd Floor Bathroom in Hall - toilet , combination tub/shower , Large Mirror, large vanity
  • 3 full baths, 2 half baths
  • 5 Bedrooms, Sleeps 16
  • Blue Skylight 3rd Floor large Master Bedroom - 1 queen , Skylights, Table and 2 chairs, side comfort chair, lamps
    Salmon Sliding Glass Deck Main 2nd flr Large Master Bedroom - 1 queen , Dressing Area, Private Full Steam Shower/Tub Bath/TV
    Yellow Skylight 3rd floor OTHER large bedroom - 1 queen , 1 twin/ single , 1 baby crib , Spacious, walk-in closet, 2 dressers, skylights
    1st floor - Iron Full Bed, Large OTHER Bedroom - 1 double , 3 twin/ single , Spacious,near game room, with door to outside & small deck
    Sliding Doors/Deck GREEN 1st Floor Large Master Bedroom - 1 queen , Dressing Area, Private Full Bath with Shower/Tub; TV, Rocker
  • All bedrooms are Spacious. All have a large area rug on hardwood floors. 2 Masters are located off the 2 decks with views of the forest. Sliding Glass doors to the decks. Lots of natural light and all Pella blinds that can be raised, lowered. or let some light in. 4 of the 5 bedrooms have Walk-In Closets. Home has Central Heat (new furnace), gas fireplace on 1st floor, Wood burning on 2nd floor and 2 additional infrared space heaters on 1st floor for an even cozier feel for those that are cold natured.
  • Books
  • DVD Player
  • Game Room ...
  • Games ...
  • Ping Pong Table
  • Satellite / Cable ...
  • Stereo ...
  • Television ...
  • Video Library
  • Deck / Patio ...
  • Golf ...
  • Outdoor Grill ...
  • Ski & Snowboard ...
  • wheelchair accessible
Pool / Spa:
  • Communal Pool ...
  • churches
  • health/beauty spa
  • playground
  • recreation center
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • bird watching
  • horseback riding
  • paddle boating
  • photography
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • hiking
  • ice skating
  • mountain biking
  • mountain climbing
  • mountaineering
  • rafting
  • rock climbing
  • roller blading
  • skiing
  • snowboarding
  • swimming
  • water tubing
Our Guests say a lot. Check our Reviews on this site. VRBO takes Reviews very seriously. Only those with Reservations are allowed to Review.


Exceptional! 5/5 -
(40 traveler reviews)

97% Complete
2% Complete
0% Complete
0% Complete
0% Complete
Guest Swimming Pool - Outdoor, Heated, Pavillion, Very close by
average rating of 4.975 based on 40 reviews
Ivyland, PA

Great Family Time in the Mountains

  • 5 of 5

We had a wonderful time at the Chestnut Place Memories home in the Wintergreen Resort. We were 2 families traveling together (5 adults, 4 adult children and twin 8 month-olds) and this home was beautiful and plenty big enough to spend time together or have some alone time. The bedrooms are bigger than the pictures show and quite comfortable. The location is great. The home is about 45 minutes from the south entrance to Shenandoah National Park and a beautiful ride. There are restaurants within a half hour drive that are very good. Check out the breweries and cideries too! Charlottesville and Monticello are about an hour away.

The home comes equipped with everything you could want, except your own food. the kitchen is plenty big enough for more than one person to prepare a meal and fully stocked with plenty of dishes, bowls, glasses and a plethora of wine glasses! Spices, paper towels and even frosted mugs were on hand. Karen and Ken have thought of everything to make a stay here great.

We had a problem with the AC on the upper level, but Karen and Ken worked it out and even got a repair man in on July 4th. The problem was fixed in no time!

It is beautiful and cool on the mountain, even in July. The decks are scenic places to sit and have coffee in the morning, read a book or enjoy an evening meal. The adventurous people in our group headed out to walk the trails within the resort - there are many ranging from a nice nature walk to a challenging hike.

There is a beautiful lake and pool available (there is a fee for lake access). The lake has paddle boats, canoes and kayaks. It is a small lake so it isn't hard to canoe around it. There is even a beach for little ones to play in the sand. There is also a mini golf course, zip line, kids sandbox (Dino Dig) and other activities at the Discovery Adventure Center nearby.

We had a great time on our Shenandoah vacation! Thank you Ken and Karen for making this a special time for our two families!

  • Submitted: Jul 9, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
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1 0

JMU Graduation House for the Family

  • 5 of 5

This house was amazing! Beautiful views from most areas of home. Parking was a breeze.... entry level parking and no walking up a million steps to home. The house is clearly well cared for and clean and comfortable. We have rented many properties from VRBO and other sites and we have NEVER had a more attentive managers than Ken and Karen! They were absolutely available to us for a number of questions and even able to offer recommendations for dinner, nearby grocery stores etc. This house is a must see and easily accommodates a family of 10-12.

Only suggestion would be to provide additional blankets in the closets. As warned, the house was a little cool in the evenings and the bead spreads are light. Fantastic space.

  • Submitted: May 17, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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Colerain, NC

Beautiful House!!

  • 5 of 5

We had a great time!! There was not very much snow, but my snowboarders made the most of it!! We would love to rent this house again next year if our budget allows!!

  • Submitted: Feb 27, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
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Beautiful House!

  • 5 of 5

We had a wonderful time. The house was a perfect fit for our 4 families. The adults and kids had a great time. Thanks

  • Submitted: Jan 22, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
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Amazing vacation home!!

  • 5 of 5

What a wonderful time we had at Chestnut Place. The home was simply beautiful and it couldn't have been nicer. We were a family of 11 and ate in each night which could have been very challenging, but the kitchen was so well equipped we had everything we could have needed and then some! The rooms were very cozy and we truly felt comfortable and at home. The pictures don't do the house justice.

The owners couldn't have been more accommodating. They communicated well with us and made sure we had everything we needed. We really made wonderful memories at Chestnut Place and a great time was had by all!

I would certainly recommend this lovely home to anyone!

  • Submitted: Jan 4, 2017
  • Stayed: Dec 2016
  • Source: HomeAway
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Awesome 5 bedroom home. Love the view! Truly handicapped except for 2 front steps. spacious!

  • 5 of 5

We had a fantastic Christmas in this lovely home. Karen and Ken Barber were extremely gracious and helpful! Anything you need, just ask. The view was amazing. At one point we had 12 people there and we all had plenty of room which is amazing. Kitchen was very nice and well stocked. The downstairs master bedroom needs a new mattress, but that is only complaint. We have rented homes at Wintergreen many times, but this home (not house) was the best!

  • Submitted: Dec 28, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
Owner's Response: Hi Lee, thank you for your beautiful Review of The Chestnut Place Memories Guest Home. You were wise to look and plan early for a Christmas week vacation. You asked questions and we measured for your special family member in a wheel chair. We love our Guests and you proved to be one of 99 per cent of those that are respectful of the lease and take excellent care of this loved home. There are many people that make our "shared" vacation homes a sucesss and help to earn your 5 Star Review and your positive comments. Included in that team are Homeowners Chris and Anne who are very proud of this home and its success as a quality, spacious, and comfortable 4 season place at Wintergreen Resort in the Blue Ridge Playground for Guests to Come2Play. They heard you loud and clear about that mattress. Today the mattress has been replaced and we all thank you for letting us know that it had earned its retirement. Lee, you and your family are special to us. We hope that you will return and stay with us again, anytime you can get away. Thank you. Respectfully, Karen and Ken, Chris and Anne, and everyone on the Guest Services Team at Vacation Rentals At Wintergreen Resort that love The Chestnut Place Memories Guest Home and our other awesome "shared" vacation homes.
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Car: necessary

A few of the activities are more than 15 minutes away if out of Resort and off the Mountain.


Rates & Availability

Wintergreen Resort House Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Labor Day 2017
Sep 1 2017 - Sep 7 2017
3 night minimum stay
Fall Leaves
Oct 1 2017 - Oct 31 2017
3 night minimum stay
Nov 19 2017 - Nov 27 2017
4 night minimum stay
Dec 19 2017 - Jan 7 2018
4 night minimum stay
Jan 11 2018 - Jan 17 2018
4 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

Damage Deposit $300

The Commonwealth of Virginia charges 5% Sales Tax. The County of Nelson charges 5.3% Lodging Tax. That is why you see the tax at 10.3%. To have a pet(s) approved, please send an email with description. The $59 insurance policy offered here is what is required for approved pet(s). An insurance link can be sent to you anytime before arrival, but insurance must be purchased before 48 hours prior to arrival or the insurance company won't write the policy. Each pet must be crated instead of being left alone in the home. Weather does not always allow for a safe fire. Firewood is provided for the wood-burning fireplace or chiminea and is $50. Leave a check at the home at departure. Guest agrees to read and accept the lease. The lease has critical information about taking care of the home, check-in and check-out procedures that must be honored to have this part of the Reservation/Security Deposit returned. Our company website should be downloaded to your cell phone so that "Hospitality" information is readily available. Guest agrees to honor, not dispute any and all credit/debit card charges initiated by Guest. This additional information note about property and/or terms was updated on 4/14/17 at 11:46 am by Karen and Ken Barber at Vacation Rentals At Wintergreen Resort.

Manager's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
Contact Manager

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