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Book Online or call HomeAway Booking Assistance 888-640-7927
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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:
May 25, 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:
  • Max. occupancy: 11
  • smoking allowed ...
  • pets not allowed
  • Events Allowed
  • children welcome
  • 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 -
(40 traveler reviews)

Farm Experience-1750's Log Home- near U. VA, Wintergreen & Vineyards.
average rating of 4.9 based on 40 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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2 1

Lovely Place

  • 5 of 5

What fun to stay in the old farmhouse. The accommodations were perfect for what we needed and the hosts went above and beyond. Thank you so much for the great weekend.

  • Submitted: Apr 28, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
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0 0

What a Charming Home

  • 5 of 5

Honestly for us there is not a thing that we needed or were not happy with. The house was perfect and so charming. There is plenty of room for 4 couples to spend time together at the dinner table or on the porch and even downstairs in the den. We very much enjoyed the screened in porch area. The farm is very peaceful and relaxing. This is located away from all the hustle and bustle of everyday life. Bill and Cynthia were very welcoming and pleasant host. They showed us everything we needed and then left us alone. The fresh cut flowers scattered around the house were amazing. We would return for another visit without question! Thanks for opening your lovely home up to us.

  • Submitted: Apr 24, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
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Simply Beautiful

  • 5 of 5

I booked this home for a bachelorette party weekend and it fit all 11 of us. Our hosts Bill and Cynthia were so welcoming and kind, I couldn't have dreamed of a better place to stay!

  • Submitted: Apr 1, 2017
  • Stayed: Mar 2017
  • Source: HomeAway
Owner's Response: Thank you for your kind words. We are so glad you enjoyed yourselves. We loved hosting you. Blessings, Bill
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A perfect location for a family!!! Truly a destination worth visiting.

  • 4 of 5

We needed a location to house my family of four, plus my parents and brother. Our biggest obstacle was finding someplace that allowed smoking on the premises, as my father smokes. I was excited about Quarter Farm, since my dad would be able to smoke outside and it had enough bedrooms so we all had our own private space. My only fear was it was a period home, and I was sure it would have antiques. I have two very active boys, and as any parent would worry I figured there would be items that might get broken. Fortunately everything was very nicely organized and it was a very family comfortable setting.

When we arrived we were greeted by Bill and Cynthia the homes owners, they live next door and run the farm where the house is located. They made us feel immediately at home, and even had prepared the best gluten free cookies I've ever eaten. They gave us a tour of the home, and had wonderful stories to share about the home and property. If you love history, you must come prepared.

The best part of our stay though was the time and patience Bill gave to my boys. He introduced them to all the farm animals, and allowed them to help feed and water the goats and chickens. My youngest sons favorite part of the whole weekend was getting to gather eggs every afternoon. We even got to keep the eggs to fix the next morning for breakfast. My other son enjoyed hiking over to the large pond to go fishing, he also enjoyed all the antique books that the home housed.

It truly was a perfect long weekend, and one I highly recommend to anyone wanting to sit back, relax and enjoy the sights and sounds of a working farm!!!

  • Submitted: Feb 20, 2017
  • Stayed: Feb 2017
  • Source: VRBO, from HomeAway
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Lovely country home for family Christmas.

  • 5 of 5

We stayed at the farm for Christmas. The home was beautiful, large and worked perfectly for our family holiday. We appreciated the care and attention given to house, including Christmas decorations! Thank you.

  • Submitted: Jan 8, 2017
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
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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 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

Cleaning Fee $150
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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