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

Bedrooms 4
Space 2,500 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:

To enjoy an aerial view of the house and farm click on the video tab in the picture above.

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 hold a day old chick in your hands. 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, honey, 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:
September 22, 2017

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. Our son graduated from James Madison University this past May.

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 Central Virginia

This farm has been a working cattle farm for 62 years. In the last 15 years I have added, goats, honey bees, 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:
  • 2500 sq. ft.
House Rules:
  • Check-in: 1:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 11
  • 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 -
(49 traveler reviews)

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Farm Experience-1750's Log Home- near U. VA, Wintergreen & Vineyards.
average rating of 4.9183674 based on 49 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: Jul 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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quiet and beautiful

  • 5 of 5

This is a beautifully located house with gorgeous views from every window, nestled in a quiet area outside of the immediate hubbub of Charlottesville city life (while still being nearby lots of attractions). The property is lovingly cared for without being "precious," so that our multi-generational group felt at home and at ease from the moment Cynthia showed us around. Everything was exceptionally clean and Bill and Cynthia anticipated all of our possible needs. Highly recommended.

  • Submitted: Aug 22, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Couldn't have had a more beautiful location for my daughter's bridal shower!

  • 5 of 5

The farm was fantastic. Our hosts could not have done any more to make our stay absolutely perfect! Far more than I could have ever imagined!

  • Submitted: Jul 27, 2017
  • Stayed: Jul 2017
  • Source: HomeAway
Owner's Response: Liz, It was so much fun, for us, having you, your daughter here at Quarters Farm for the week-end. You had such a beautiful bridal shower. The highlight for us was being asked to judge the bridal dress contest... so cute. Blessings to all and our very best to the bride!
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Superb multi-generation family vacation location

  • 5 of 5

The McCaskills could not have been better hosts. The farm is easily the best vacation location we have had. Our grandchildren eagerly looked forward to every morning and raced down the stairs to help Bill with the farm chores: milking goats, feeding chickens and Sir Galahad and in the evening gathering eggs. We were also close enough to Charlottesville and Staunton that every day we ventured out to enjoy historical attractions and entertainment. And yet at the end of the day we were far enough out to enjoy peace and quiet. The big historical farm house was very welcoming, spacious and comfortable for three generations. The well outfitted kitchen had everything we needed. We will definitely come back again for another family gathering and building memories.

  • Submitted: Jul 17, 2017
  • Stayed: Jun 2017
  • Source: Vacation Rentals, from HomeAway
Owner's Response: Thank you for the kind review. We certainly enjoyed hosting your family. Blessings, Bill
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Bucolic setting for family reunion

  • 5 of 5

Quarters Farm was the perfect place for a family get together in this beautiful home. Very comfortable, nicely decorated with wonderful welcoming hosts, Cynthia and Bill. In the mornings we enjoyed coffee and the beautiful mountain view from the porch. Our grandchildren had plenty of room to run and play and they loved all the farm animals, especially the goats. The farm was conveniently located, close to the airport, downtown Charlottesville and wedding venues. Quarters Farm will be a very warm memory for our family and we hope that we will be able to meet there again.

  • Submitted: Jun 29, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
Owner's Response: Susan, It was joy having you and your family with us for the weekend. You blessed us as well. Cynthia
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Lovely farmhouse!

  • 5 of 5

Our family loved our experience at this farmhouse. Bill and Cynthia were generous hosts, helping our children learn to milk a goat and pick up eggs from the chicken coop each day. They made a special effort to introduce our children to life on their farm, and they were warm and kind as they did so. The home itself was spacious and well-appointed; we wanted for nothing. We had a marvelous visit, and our family will remember this vacation for a long time! We were sorry when our stay was over. Thank you for a great holiday and wonderful memories!

  • Submitted: Jun 25, 2017
  • Stayed: Jun 2017
  • Source: VRBO, from HomeAway
Owner's Response: We also enjoyed hosting your family. We are always excited to show children where food really comes from. Blessings, Bill
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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

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.

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