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Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Photo gallery for Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

You approach the property from this side.
The original front of the oldest part of the house.
View from the porch in Spring of 2020
Screened in porch. It has become one of the favorite places to relax.
Kitchen

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms2 bathroomsSleeps 113100 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Outdoor Space

Rooms & beds

4 bedrooms (sleeps 11)

East Bedroom

1 Queen Bed and 2 Twin Beds

Master Bedroom

1 King Bed and 1 Twin Bed

South Bedroom

2 Twin Beds

West Bedroom

1 Queen Bed

2 bathrooms

Master Bathroom

Soap · Towels provided · Toilet · Shower only · Hair dryer

Upstairs Bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

About this property

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

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! The owners live in a separate cottage a short distance away and are available for help or emergency.

You can 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 275 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 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.

ALERT: Due to the design of this historic home, there are NO bathrooms/bedrooms on the ground floor. Access to the living areas is via a flight of stairs.

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.

Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 1:00 PM
Minimum age to rent: 19
Check out before 12:00 PM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking allowed: in designated areas
Smoking is only allowed outside the house

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the neighborhood

Charlottesville

Located in Charlottesville, this vacation home is in a rural area. Luther P. Jackson Cultural Center and Charlottesville Ice Park are local attractions and those in the mood for shopping can visit Downtown Mall and Corner District. Traveling with kids? Consider Virginia Discovery Museum, or check out an event or a game at Scott Stadium. Water skiing and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and cycling nearby.
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Map
Charlottesville, VA

What's nearby

  • Ragged Branch Distillery - 8 min drive - 7.9 km
  • Ruby Canody Gallery - 10 min drive - 10.3 km
  • King Family Vineyards - 11 min drive - 11.9 km
  • University of Virginia - 13 min drive - 18.9 km
  • Scott Stadium - 15 min drive - 20.3 km

Getting around

  • Charlottesville Station - 24 min drive
  • Charlottesville-Albemarle Airport (CHO) - 29 min drive

Restaurants

  • ‪Fiesta Azteca Tap House And Mexican Kitchen - ‬13 min drive
  • ‪King Family Vineyards - ‬15 min drive
  • ‪Starr Hill Brewery - ‬14 min drive
  • ‪Dr. Ho's Humble Pie - ‬16 min drive
  • ‪Wisdom Oak Winery - ‬28 min drive

Frequently asked questions

Is Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious?

As of Apr 3, 2026, prices found for a 1-night stay for 2 adults at Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious on Jul 3, 2026 start from $377, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious?

Check-in begins at 1:00 PM.

What time is check-out at Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious?

Check-out is at 12:00 PM.

Where is Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious located?

Located in a rural location, this family-friendly vacation home is within 9 mi (15 km) of Ragged Branch Distillery, Ruby Canody Gallery, and King Family Vineyards. Starr Hill Brewery and Pippin Hill Farm & Vineyards are also within 9 mi (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 251 out of 258 reviews
Rating 8 - Good. 7 out of 258 reviews
Rating 6 - Okay. 0 out of 258 reviews
Rating 4 - Poor. 0 out of 258 reviews
Rating 2 - Terrible. 0 out of 258 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Shayna H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hosts were extremely gracious and communicative. Property was rustic and cozy. Location was excellent.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Marianne S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The kitchen was well equipped and bedrooms were very comfortable. The farm setting was very relaxing and calming. Cynthia and Bill were the kindest hosts and most welcoming.
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Bill B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another wonderful stay at this glorious home. Great hosts. Lovely surroundings. We'll be back again next year for sure!!
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Christine M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is an absolutely lovely property, with incredibly friendly and helpful hosts.The screened porch is such a wonderful place to sit and enjoy folks' company, while taking in the views, which are glorious. The animals wandering about are so sweet. We have stayed here twice now, and would recommend it heartily.
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Stephanie C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely time on the farm. Bill and Cynthia are so accommodating and were great with our kids. They absolutely loved feeding the chickens and goats each morning. We will certainly be back!
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Crystal D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

Thanks for a wonderful stay at your beautiful farm! Great location for visiting wineries and Charlottesville.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Ann Miller W. M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We can’t wait to get back! Our cups are full - thank you for everything!
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Lisa P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My girlfriends and I were enchanted by the farm and so enjoyed the animals. The house was extraordinary built in the 1700’s. The owners were very gracious and decorated the whole house with fresh flowers from their garden not to mention the fresh eggs.. I highly recommend this unique experience!
Sunrise from the porch
Beautiful property
Donkey greeting
Beautiful fresh flowers
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Vedant D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay at a historic place

Great hosts and were very friendly
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

GinnynGreg S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My kids and grandkids stayed here before a wedding at our house. The children loved collecting eggs and feeding the chickens and goats each day and my daughters appreciated the beautiful fresh flowers arranged in all the rooms. The kitchen and bathrooms were all well stocked and the grounds are gorgeous. Cynthia and Bill were consummate hosts and treated everyone like family!
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Preston R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice, peaceful location. House was very clean and everything you needed was provided. Bill and Cynthia were there for all your needs. The family enjoyed the watching the cows, chickens, horses and goats..
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

DANIEL N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place to stay for graduation

We stayed here over graduation weekend and it couldn't have been more perfect. The hosts were great, friendly and helpful. I was nice to be a little away from the craziness. The house is amazing and the grounds were awesome too!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Kelly B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
What a delight! The house is incredibly clean and comfortable. The kitchen was well stocked and fresh eggs were offered. Cynthia and Bill were wonderful and welcoming hosts, and accommodated our requests for getting to see the animals. Walking the beautiful property, drinking coffee on the screened porch, it was picturesque. Thank you Quarters Farm!
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Tom E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful place, gracious hosts

Wonderful restored property and gracious hosts that made our stay that much better
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Tom L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing property, not to be missed!

My friends and I really enjoyed our experience of staying here. It's in a beautiful, serene setting with gorgeous views. The hosts were wonderful, the animals were incredible . . . we would love to stay here again!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Allen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome place and hosts

Everything was perfect... We hope to stay again!
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Liam M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend

Very friendly hosts, spacious property, great gathering spaces within the house that made for a great time in Charlottesville.
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Leigh H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
From the very second you enter this property you are made to feel welcomed and appreciated. Whether it is from Cynthia, Bill or the incredible Pyrenees Zoe. Taking time out of their day to ensure you have the most amazing time is always done with a smile and a great chat. The house is phenomenal, from the history to the comfort it was absolutely 5 stars. Greeting and feeding the animals most days, spending the afternoons in the covered patio and the evenings downstairs by the fire made this an extremely relaxing and memorable vacation. A short drive to everywhere, we spent time at the historic downtown mall, visited Monticello, and frequented the many wineries surrounding the property, before coming “home” to a warm welcome and incredible vistas. I also highly recommend utilizing Darby Farms for the catering, the food was amazing as was the service. Thankyou, Bill and Cynthia for an incredible home away from home Vacation!!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Kathleen B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring break with a son and his young family

The farm experience was delightful for the children, ages 7, 5, 3, and 1.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Kevin V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved our stay!

We had a wonderful time time staying here. The house and setting are amazing! The hosts are so welcoming and made us feel like family while we were there. I would love to plan another trip back here.
Stayed 3 nights in Dec 2021
Verified

10/10 Excellent

John G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great experience

Loved the location and history of the house - great for a weekend getaway from the city and great hosts!
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Esther K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

An amazing treat to experience !

My family and I had an amazing time at Quarters Farm and was astonished by the beauty of the home! Words can’t describe the decor and comfort the home feels. Must stay!
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Jim N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Country Retreat

Group of us there for a local wedding. Perfect location midway between the city and the wedding venue. Idyllic setting, terrific hosts.
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Bill B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

College Reunion

Fantastic home and wonderful hosts!!
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Bradford F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely Fabulous!

The house and farm are just beautiful. We spent nearly the entire stay on the screened porch listening to the birds, watching the horses, goats, and chickens and enjoying the quiet serenity of the country. Our hosts could not have been more gracious and welcoming. We wondered around the property and soaked up the country, ate some amazing farm raised eggs, and made several excursions to nearby Monticello, antique shops, UVA, and 1799 at the Clifton for dinner. I highly recommended this beautiful place for anyone staying in the Charlottesville area.
Stayed 3 nights in Jun 2025

About the host

Hosted by Cynthia L McCaskill

Host profile image
I grew up in Waynesboro, Va. and my wife grew up in Lynchburg, Va. We have both lived overseas in Ireland; Singapore and Thailand, as well as Mississippi and Atlanta before returning to central Virginia 21 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.

Why they chose this property

This farm has been a working cattle farm for 70 years. In the last 21 years I have added, goats and laying hens We have lawns and gardens and enjoy living in Central Virginia

What makes this property 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. The owners live a short distance away in a separate home and are available for help or emergencies.

Languages:

English

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