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

(38 Reviews)

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View from the back door to deck at dusk. Tiled kitchen floor & hardwood floor


Last updated: 04/25/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates
  • Minimum stay:2-4 nights
  • Sleeps:16
  • Bedrooms:5
  • Bathrooms:3.75
  • Property type:House
  • Internet:Yes
  • Pets considered:Yes
  • Wheel chair accessible:Yes

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
Send email


Member since: 2003

Speaks: english
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/25/2017

Property Type

  • House
  • 2567 sq. ft.

House Rules

  • Max. occupancy 16
  • Events Allowed
  • Minimum Age Limit For Renters:

    Renter signing the lease and responsible for all guests and responsible for the property must be at least 25 years of age....moreless

  • Children Welcome
  • Non Smoking Only
  • Pets Considered:

    Must discuss at or near time of reservation. Generally approved. Guest responsible for dog bites, will always crate pet when not at the home. Must purchase $59 insurance policy. Lease addendum for pet rules. ...moreless

Accommodation Type

  • Vacation Rental


  • Guests Provide Their Own Meals


  • Wheelchair Accessible

Bedrooms: 5 Bedrooms, Sleeps 16, Beds for 16

  • Blue Skylight 3rd Floor large Master Bedroom: 1 queen

    Skylights, Table and 2 chairs, side comfort chair, lamps...moreless

  • Salmon Sliding Glass Deck Main 2nd flr Large Master Bedroom: 1 queen

    Dressing Area, Private Full Steam Shower/Tub Bath/TV...moreless

  • Yellow Skylight 3rd floor OTHER large bedroom: 1 queen, 1 twin/ single, 1 baby crib

    Spacious, walk-in closet, 2 dressers, skylights...moreless

  • 1st floor - Iron Full Bed, Large OTHER Bedroom: 1 double, 3 twin/ single

    Spacious,near game room, with door to outside & small deck...moreless

  • Sliding Doors/Deck GREEN 1st Floor Large Master Bedroom: 1 queen

    Dressing Area, Private Full Bath with Shower/Tub; TV, Rocker...moreless

  • 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. ...moreless

Bathrooms: 3 Bathrooms, 2 Half Bathrooms

  • 2nd Floor (Main) Floor Bathroom in Hall: toilet

    Pedestal sink, mirror...moreless

  • 1st Floor Master Bathroom: toilet, combination tub/shower

    Mirror, sink, and dressing area outside bath; linen closet...moreless

  • 2nd Floor (Main) Master Bathroom: toilet, combination tub/shower

    Mirror, sink, and dressing area, STEAM BATH!, Linen closet...moreless

  • 1st Floor Bathroom in Hall: toilet

    Mirror, sink, vanity, counter top...moreless

  • 3rd Floor Bathroom in Hall: toilet, combination tub/shower

    Large Mirror, large vanity...moreless

  • 3 full baths, 2 half baths

Other Amenities

  • Our Guests say a lot. Check our Reviews on this site. VRBO takes Reviews very seriously. Only those with Reservations are allowed to Review....moreless


  • Books
  • DVD Player
  • Game Room:

    Ping Pong Table; ...moreless

  • Games:

    Ping pong table; some board games...moreless

  • Ping Pong Table
  • Satellite / Cable:

    Nelson Cable ...moreless


  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions


  • Churches
  • Health/Beauty Spa
  • Playground
  • Recreation Center
  • Restaurants
  • Winery Tours

Local Services & Businesses

  • ATM/Bank
  • Groceries
  • Hospital
  • Massage Therapist
  • Medical Services

Leisure Activities

  • Antiquing
  • Bird Watching
  • Horseback Riding
  • Paddle Boating
  • Photography
  • Scenic Drives
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing

Location Type

  • Downtown:

    Waynesboro closest; Charlottesville next; both have Walmarts and grocery stores...moreless

  • Golf Course View:

    Walking distance to Mountaintop Golf Course. Golf Golf Cart Paths make great walking and photographic trails. ...moreless

  • Mountain View:

    Can see some of the ski slopes from the decks during ski season....moreless

  • Resort
  • Rural:

    Many beautiful walks, hikes, trails....moreless

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


  • Dining:

    2 Dining Tables can be arranged together to seat 12 and 2 at nearby island....moreless

  • Dining Area
  • Seating for 12 people


  • Air Conditioning:

    Central Air available, 10 degree lower temperature than the valley, and normally a breeze. Sleep like a baby with the open windows. Ceiling fans in all bedrooms....moreless

  • Clothes Dryer
  • Fireplace:

    Wood burning fireplace on the main level living room off the kitchen.Gas burning fireplace in lower level family room. Wood provided with notice. $50 delivered, stacked. Qty photo upon request....moreless

  • Hair Dryer
  • Heating:

    Heat Pump ...moreless

  • Internet:

    High speed, unlimited, great for streaming movies/Netflix - Nelson Cable Company...moreless

  • Iron & Board
  • Linens Provided:

    All linens provided....moreless

  • Living Room:

    Wood burning fireplace. Sofa, love seat, Wide Screen TV, cathedral ceilings, 2 sliding glass doors to large wrap around deck. Table and chairs for 6 by the windows....moreless

  • Parking:

    Nice parking of about 4 vehicles. No difficult incline to deal with like most homes. Homes were built at the top and side of the mountain for the breathtaking views....moreless

  • Towels Provided:

    All towels are provided...moreless

  • Washing Machine:

    Complimentary washing detergent and fabric softener provided....moreless

  • Wood Stove:

    Chiminea located on Main Floor (2nd) deck with fire starters....moreless


  • Coffee Maker:

    2 Coffee Makers: 1. Hamilton Beach Dual coffee maker: 2 Way Flex Brew - Choose Single K-Cup packs or a 12 cup full pot 2. 12 cup full pot...moreless

  • Dishes & Utensils:

    Fine dining and drinking; Some paper and plastic....moreless

  • Dishwasher


  • Deck / Patio:

    Large decks with lots of furniture nestled in the forest. Also large glass table and umbrella...moreless

  • Golf:

    Stoney Creek Golf is open to the public....moreless

  • Outdoor Grill:

    New gas grill with extra full tank....moreless

  • Ski & Snowboard: for everything you want to know about slopes, levels, tickets, equipment, lessons....moreless

Pool / Spa

  • Communal Pool:

    .4 mile level walk to Chestnut Springs outdoor summertime pool nestled in the forest. Life Guard(s), heated. Large Pavillion with seating and a grill....moreless



Write a review 5
from 38 traveler reviews
Rental basis: Per property
Dates Nightly Weekend Night Weekly Monthly * Event
Memorial Day 2017
May 26 - Jun 29, 2017
3 night min stay
Fourth of July 2017
Jun 30 - Jul 6, 2017
3 night min stay
Labor Day 2017
Sep 1 - Sep 7, 2017
3 night min stay
Fall Leaves
Oct 1 - Oct 31, 2017
3 night min stay
Nov 19 - Nov 27, 2017
4 night min stay
Dec 19 - Jan 7, 2018
4 night min stay
Jan 11 - Jan 17, 2018
4 night min stay
My Standard Rate
2 night min stay

Additional information about rental rates


  • Refundable Damage Deposit $300
  • Tax Rate 10.3%


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 for cancellations more than 30 days before check-in date.

100% refund for cancellations more than 60 days before check-in date.

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Last updated: 04/25/2017
Check availability
23 Available
21 Unavailable
22 Today
23 Selected dates


Car: Necessary

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


Manager info

About: 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 Wintergreen, VA, USA:
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.

The Unique Benefits at this House:
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

Contact us

Speaks: english
Response time: Within an hour
Response Rate: 100%
Calendar last updated: 04/25/2017

Send email

Links to more information:



  • View from the back door to deck at dusk.  Tiled kitchen floor & hardwood floor

    View from the back door to deck at dusk. Tiled kitchen floor & hardwood floor

  • Living Room, Cathedral Ceiling, Pella Windows and blinds.

    Living Room, Cathedral Ceiling, Pella Windows and blinds.

  • Wintergreen Resort, Bear Walk Trail, The Blue Ridge Playground - Wildlife Camera

    Wintergreen Resort, Bear Walk Trail, The Blue Ridge Playground - Wildlife Camera

  • The Front of the home from the street below during the cold months

    The Front of the home from the street below during the cold months

  • Ski Season View from the Deck - Eagles Swoop Ski Trail

    Ski Season View from the Deck - Eagles Swoop Ski Trail

  • A place to eat or play in the central air conditioning.

    A place to eat or play in the central air conditioning.

  • Sit and eat or talk or sun bathe

    Sit and eat or talk or sun bathe

  • Lower floor family room with gas fireplace.

    Lower floor family room with gas fireplace.

  • Main Floor Master, sliding glass doors to deck.

    Main Floor Master, sliding glass doors to deck.

  • Top floor Master with Skylights, table and chairs, closet, side chair

    Top floor Master with Skylights, table and chairs, closet, side chair

  • Bottom floor Master with sliding glass doors to deck

    Bottom floor Master with sliding glass doors to deck

  • One of our many neighbors

    One of our many neighbors

  • Well equipped kitchen

    Well equipped kitchen

  • Dining Area across from kitchen.

    Dining Area across from kitchen.

  • The level back of the home - parking area for about 4 cars

    The level back of the home - parking area for about 4 cars

  • The Front of the home from the street below - green, green, green.

    The Front of the home from the street below - green, green, green.

  • Scenic Overlook near the home.

    Scenic Overlook near the home.

  • Top Deck with outdoor eating and chiminea

    Top Deck with outdoor eating and chiminea

  • Ping Pong anyone, sit on the lower deck

    Ping Pong anyone, sit on the lower deck

  • Top Floor extra bedroom with a queen, twin, crib, walk-in closet

    Top Floor extra bedroom with a queen, twin, crib, walk-in closet

  • Bottom Level - Extra Bedroom - 3 singles - 1 full

    Bottom Level - Extra Bedroom - 3 singles - 1 full

VRBO #602015

This listing was first published here in 2014.

Date last modified - Thursday, April 27, 2017

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