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

Farm Experience-1750's Log Home- near U. VA, Wintergreen & Vineyards.

Bedrooms 4
Space 3,100 sq. ft.
Property type house
Minimum Stay 2 - 3 nights


About the property

4 bedroom, 2 bath with living room, dining room and kitchen and Mountain Views

Country Get-a-way:

The GPS address is, 5114 Dick Woods Road, Charlottesville, VA 22903.

Are you looking to get away from the hustle and bustle of 21st century living, step back in time 200 years in order to enjoy the rhythms of nature? Come listen to the rain on a tin roof and sleep in the morning until you are finished.

You and your children can feed the chickens, collect eggs, milk goats or go for a long walk. Due to bio-security and health issues we have a strict no pet policy.

You can meet Sir Galahad, the Great Pyrenees, ring the dinner bell or hang out in the "Man Cave" with the 42 inch flat screen TV. Come away and relax with a glass of wine in the cool of the evening as all the stars in the Milky Way pop out to greet you.

The most amazing part of this saga is that it is available only a short 14 minute drive from the Rotunda at University of Virginia. Quarters Farm is also only 15 minutes from Pippen Hill Vineyard, King Family Vineyard and Pollack Vineyard. We are 45 minutes from Wintergreen and close to many fine restaurants.

One new addition is a catering service provided by close friends. They can have the frig stocked when you arrive, or cater a meal during your stay. Prices and information sent upon request.

The history of the farm only adds to the mystique. In 1745 King George of England granted 1800 acres to the Mills family who moved to Virginia and had a three story home built with 6 rooms for themselves and their three sons. This home predates the beginning of construction on Thomas Jefferson's Monticello by 18 years. In the 260 years since then, wings and additions have been added on to the original stone and log construction

My father purchased 180 acres, along with the house, in 1952. It is now a sustainable farm selling grass fed beef, pastured eggs, and other products which are all available to our guests. My wife and I live in a house close by and run the farm.

A beautiful kitchen attached to a large screened-in porch, along with a second story porch for enjoying the mountain views with your favorite beverage. 4 bedrooms and two bathrooms will comfortably meet your needs

We believe that you will find this home truly inviting and relaxing, well furnished with antiques and beautiful furniture. The house has a whole house generator, so you will not have to leave in the case of a power outage.

More Details

Bill and Cynthia McCaskill 5114 Dick Woods Rd; Charlottesville, VA 22903
Member since: 2014
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
March 15, 2018

About Bill and Cynthia McCaskill 5114 Dick Woods Rd; Charlottesville, VA 22903

I grew up in Waynesboro, Va. and my wife grew up in Lynchburg, Va. We have both lived overseas in Ireland and Thailand, as well as Mississippi and Atlanta before returning to central Virginia 15 years ago. I graduated from N. C. State and Reformed Theological Seminary, my wife graduated from M.C.V. in Richmond and Belhaven College in Jackson, Mississippi.

Bill and Cynthia McCaskill 5114 Dick Woods Rd; Charlottesville, VA 22903 purchased this house in 1952

Why Bill and Cynthia McCaskill 5114 Dick Woods Rd; Charlottesville, VA 22903 chose Charlottesville

This farm has been a working cattle farm for 62 years. In the last 15 years I have added, goats, laying hens and Great Pyrenees. We have lawns and gardens and enjoy living in Central Virginia

What makes this house unique

We believe the history, location, pastoral setting, and working farm make this home unique and a place that your family or group will remember for years to come.


Charlottesville House Accommodation and Amenities

Property Type:
  • house
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
Floor Area:
  • 3100 sq. ft.
House Rules:
  • Check-in: 1:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 11
  • Children welcome
  • Parties/events allowed
  • Pets not allowed
  • Non smoking only ...
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Garage ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Room
  • seating for 8 people
  • 2 Bathrooms
  • Master Bathroom - toilet , shower
    Upstairs Bathroom - toilet , combination tub/shower
  • 4 Bedrooms, Sleeps 11
  • West Bedroom - 1 queen
    Master Bedroom - 1 king , 1 child bed , One roll away bed is also available in an adjacent room.
    South Bedroom - 2 twin/ single
    East Bedroom - 1 queen , 1 twin/ single , 1 child bed
  • Books
  • Satellite / Cable
  • Television ...
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill
  • Ski & Snowboard ...
  • churches
  • library
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • scenic drives
  • walking
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • equestrian events
  • fly fishing
  • freshwater fishing
  • hiking
  • hunting
  • pier fishing
  • skiing
We are a working farm nestled in an area steeped in history with the University of Virginia and Monticello. The region is teeming with wineries, breweries and a wide variety of international cuisine.


Wonderful! 4.9/5 -
(56 traveler reviews)

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Farm Experience-1750's Log Home- near U. VA, Wintergreen & Vineyards.
average rating of 4.928571 based on 56 reviews

Fantastic stay at the farm! Great place for children or relaxation in peaceful beautiful place.

  • 5 of 5

This is the perfect place to stay in the Charlottesville area especially with children. The house is comfortable and roomy and the screened in porch is a great place to hang out. You can also sit on the veranda and watch children catch butterflies. Collecting eggs and feeding the goats was fun and the fresh eggs each day were delicious. Bill and Cynthia are wonderful hosts ready to provide anything you need and the fresh flowers scattered throughout the house were beautiful! Winery tours and Monticello are close by. All in all the perfect place to stay and we hope to be back.

  • Submitted: Aug 6, 2017
  • Stayed: July 2017
  • Source: HomeAway
Owner's Response: We loved having you all. We also enjoyed watching the children catch butterflies. Glad you had a great time. Please come again!
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Cozy, charming, relaxing, clean and comfortable, great views!

  • 5 of 5

Our children and grandchildren stayed 5 nights at this wonderful place to ring in 2018 and it couldn't have been better! Sir Galahad the gorgeous white Pyrenees, the goats, chickens and yes, those roosters, and of course Bill ( and Cynthia, who I unfortunately missed meeting) made our visit complete. Due to weather in the single digits and my own broken ankle we stayed inside a lot.....and what a great house to hang out in! Trips to wineries, breweries, bookstores, artisan shops ( go visit the Barn Swallow!) , Beverdero on New Years Eve, coffee at the Mudhouse, a mass on New Years Day at the monastery, just driving around taking in the gorgeous landscape in winter......loved it. Want to return in spring or fall to sit on the great porch!!!!!! Thank you Bill and Cynthia, I hope to be back!!!! xoxoxo Cindy Wooten

  • Submitted: Jan 2, 2018
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
Owner's Response: Cindy, We loved hosting you and your family. Cynthia is also sorry not to have met, but will do next time. Your review will also help future guests decide if this is right for them, Thanks so much, Bill
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1 0
Baltimore, MD

Beautiful region, friendly hosts

  • 5 of 5

We had a great stay at Quarters Farm. The property is older, and the kids loved exploring all the rooms. Cynthia and Bill had the place all decorated for Christmas and we felt right at home. My daughter is still talking about the farm animals. We went on some neat field trips while we were in the area and we were heading home for Christmas, but on the drive home she kept saying, "I wish I was back at the farm. I miss it already!"

The only advice I would give for another traveler is that the stairs are steep, if anyone in the party has mobility issues. Also, it is out in the country, so there are insects and spotty cell coverage.

  • Submitted: Dec 25, 2017
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
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Fantastic Weekend!

  • 5 of 5

We loved our stay with Bill and Cynthia. The property is stunning and they were very accommodating. I would happily recommend a stay here.

  • Submitted: Nov 6, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Beautiful property!

  • 5 of 5

We had such a wonderful time! The house and property are beautiful! It was so nice to sit outside on the screened porch and watch the cows, goats and chickens.

The house had everything you would need. Plenty of linens and towels. Kitchen was fully equipped, there was even half and half, butter and eggs from the farm in the fridge for us.

Bill and Cynthia were wonderful hosts. The kids had a great time helping with daily farm chores, which included feeding the chickens and gathering their eggs every evening. Sir Gallahad (the dog) was always there to greet us upon returning to the house. We will certainly be back!

  • Submitted: Nov 6, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
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Beautiful setting, quiet, peaceful farm setting. A true getaway experience

  • 5 of 5

Owners were great. Farm and house lovely with everything you need and responsive if a problem. We are hoping to return and sharing the listing with several friends. Awesome weekend

  • Submitted: Oct 22, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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King Family Vineyards
Great vineyard, great people, great polo.
Nearest Airport
15 Miles
Charlottesville Regional Airport
Nearest Golf
7 Miles
Old Trail Golf Course
Nearest Motorway
4 Miles
Interstate 64
Nearest Ski
25 Miles

We are 12 miles from University of Virginia, 18 miles from Monticello, home of Thomas Jefferson, 20 miles from Wintergreen ski and golf resort. There are many winery tours, micro brewerys and restaurents.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $150
Additional Guest Fee $30 per person per night

Owner'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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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