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

Bedrooms 4
Property type house
Minimum Stay 2 - 3 nights

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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.

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:
January 16, 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.


Wonderful! 4.9/5 -
(35 traveler reviews)

Farm Experience-1750's Log Home- near U. VA, Wintergreen & Vineyards.
average rating of 4.9142857 based on 35 reviews

Great place to stay and explore Charlottesville

  • 5 of 5

Five stars is not enough. Bill and Cynthia are wonderful hosts. They made us welcome from the moment we drove up. The fresh flowers throughout the house and fully stocked kitchen were great. A true working farm, Bill let our grandson help him feed the chickens, gather eggs, and feed the goats. What a unique experience. The house was convenient to Monticello, Charlottesville and many many super wineries. When we weren't touring, the house was super comfortable, and a quiet, relaxing place to hang out. If you are planning a trip to the Charlottesville area, STAY HERE!

  • Submitted: Jul 28, 2016
  • Stayed: Jul 2016
  • Source: HomeAway
Owner's Response: Robert, Thanks for the kind review. We enjoyed having you here as well, come back anytime. Blessings, Bill
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1 0

Great Getaway

  • 5 of 5

Coming from Charlottesville, this is an easy drive. We came up from the south and the farm seemed really remote via the back roads.

The house is charming, with lots of room. We were two families of 5 and there was room for all of us at the dining room table, and beds for everyone. It was very clean with comfortable beds and fluffy towels. The kitchen was fully stocked with pots and pans that we used as we made dinner every night.

Our hosts were gracious and helpful, instantly responding to our every request. We had fun feeding chickens and goats and tasting the maple water and maple syrup Bill was working on.

The room in the basement, with cozy sofas, a TV and games was a favorite hang out for the kids and the adults. Most of the rooms had heaters so there were no thermostat wars among the various temperaments. Extra blankets too.

It's about 45 minutes to Wintergreen, and less than twenty to Charlottesville sights.

We recommend this to anyone except if you have trouble with stairs.

  • Submitted: Jan 2, 2017
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
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0 0

Wonderful Cabin Retreat!

  • 5 of 5

We had a wonderful stay at Bill and Cynthia's cabin, the house itself is beautiful and historic and the property it sits on is amazing. Both Bill and Cynthia were so responsive and accommodating and we had a truly wonderful time staying at their property!

  • Submitted: Oct 18, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the kind review. We truly enjoyed hosting your group as well. Come again anytime. Bill
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1 0

beautiful & historic

  • 5 of 5

My family and I spent the weekend at Quarters Farm while attending a wedding at UVA. The house was absolutely beautiful, filled with antiques, and we enjoyed hearing about it's history. It was clear the McCaskill's have taken great care of this home. Everything we could possibly need was right there, including a variety of coffee and even shampoo and conditioner. Unfortunately we did not have time to explore the working farm (my toddler loved hearing the cows and chickens from the screened-in porch!). We may return in the future, this house can easily be a destination itself!

  • Submitted: Oct 10, 2016
  • Stayed: Sep 2016
  • Source: HomeAway
Owner's Response: Thank you so much for taking the time to write a review. As you know it helps future guests find just the right location. We loved hosting your group. Thanks again, Bill
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1 0
Baltimore, md

Everything was perfect!! We had the best time!!

  • 5 of 5

Beautiful home, so peaceful!! Definitely will stay again!

  • Submitted: Sep 28, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
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0 0
Charlottesville, VA

Relaxing and Peaceful Bachelorette Weekend

  • 5 of 5

We had a great relaxing weekend at this house, the owners were great hosts. The pictures do not do the house justice. There was plenty of room for our group of 7 women. The rooms themselves are large, the views were beautiful, and you could feel the history of the home (the oldest part of the house is older than Monticello!).

We spent most of our time relaxing on the screened in porch. The ability to cook our meals over the weekend was a big plus as we wanted to focus on being together. The goats, chickens, and cows are visible from the house. They even gave us a dozen eggs - can't get a fresher breakfast than that. Truly a farm experience. One of us even got to milk a goat!

Bill and Cynthia's house is right on the property, so they were only a walk or a text message away. I would definitely recommend this house.

  • Submitted: Sep 21, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for taking the time to write such a kind review. We enjoyed hosting your group. Please come again any time. Blessings, Bill
Did you find this review helpful?
1 0


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

Charlottesville House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
UVA Graduation
May 18 2017 - May 20 2017
3 night minimum stay
Flat fee
Uva Graduation
May 17 2019 - May 20 2019
3 night minimum stay
Uva Graduation
May 15 2020 - May 18 2020
3 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

Tax Rate 10.3%

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.
Enter dates for accurate pricing
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Available arrival
Available stay (no arrival)


Charlottesville House Accommodation and Amenities

Property Type:
  • house
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
Floor Area:
  • 2500 sq. ft.
  • 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 ...
  • Events Allowed
  • children welcome
  • pets not allowed
  • smoking allowed ...
  • 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.

Learn more about this vacation rental at the owner's website:

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