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

Family-friendly holiday home in Charlottesville

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
Exceptional
4 bedrooms2 bathroomsSleeps 113100 sq ft

Popular amenities

  • Dryer
  • Barbecue grill
  • Washer
  • Fireplace
  • Parking available

Explore the area

View in a map
Charlottesville, VA
  • Place, University of Virginia
    ‪16 min drive‬
  • Place, University of Virginia Hospital
    ‪19 min drive‬
  • Place, Monticello
    ‪24 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪29 min drive‬

Rooms & beds

4 bedrooms (sleeps 11)

East Bedroom

1 Queen Bed and 1 Child Bed

Master Bedroom

1 King Bed and 1 Child Bed

South Bedroom

2 Single 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

Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Charlottesville

Located in Charlottesville, this holiday home is in a rural area. Ruby Canody Gallery and The Fralin Museum of Art are cultural highlights, and travellers looking to shop may want to visit Downtown Mall and Corner District. Travelling with kids? Consider Charlottesville Ice Park, or check out an event or a game at Scott Stadium. Waterskiing and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and hiking nearby.
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Map
Charlottesville, VA

What's nearby

  • University of Virginia - 16 min drive - 18.9 km
  • Pippin Hill Farm & Vineyards - 17 min drive - 16.0 km
  • University of Virginia Hospital - 19 min drive - 21.3 km
  • Downtown Mall - 21 min drive - 24.4 km
  • Monticello - 24 min drive - 27.2 km

Getting around

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

Restaurants

  • ‪Fiesta Azteca Tap House And Mexican Kitchen - ‬13 min drive
  • ‪Starr Hill Brewery - ‬14 min drive
  • ‪Dr. Ho's Humble Pie - ‬16 min drive
  • ‪Sal's Pizza - ‬13 min drive
  • ‪Praha Bohemian Bakery & Cafe - ‬13 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.

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?

Checkout 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 holiday 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 miles (15 km).

Reviews

10

Exceptional

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
Rating 10 - Excellent. 244 out of 251 reviews
Rating 8 - Good. 7 out of 251 reviews
Rating 6 - Okay. 0 out of 251 reviews
Rating 4 - Poor. 0 out of 251 reviews
Rating 2 - Terrible. 0 out of 251 reviews

Reviews

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

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

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

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

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

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

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

10/10 Excellent

Renay M.

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

Brooks and Dunn concert

We went to the John paul jones arena during our stay. It was easy to get to from the farm. We wish we would have had more time to just hang out at the farm, relaxing. The screened in porch was lovely for relaxing and watching the animals. We loved the decor and the whole vibe of the place. Hosts were very gracious, we would love to a return trip in the future.
Stayed 2 nights in Mar 2025

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

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

10/10 Excellent

Jenn S.

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

Lovely home and lovely hosts!

A beautiful historic property and working farm, it was the perfect getaway for some lifelong friends looking to get away. Bill and Cynthia are wonderful hosts and the home has everything you could need. It is very large and can easily accommodate a large family or group event.We were even given samples of maple water from the frees, and farm-fresh eggs! We would definitely stay here again.Thank you Bill and Cynthia for a perfect weekend.
Stayed 2 nights in Jan 2025

10/10 Excellent

Sue B.

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

A peaceful retreat

This is our second time to stay here and it was again so relaxing! The hosts are awesome and let us enjoy chicken feeding and goat milking. The grounds are beautiful and the place is restful with a screened in porch for fellowship and food since the weather was cool. Definitely our go to place in the area!
Stayed 4 nights in Jun 2024

10/10 Excellent

Walter T.

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

Perfect stay near Charlottesville.

Wonderful and well restored farm house in a beautiful area in close proximity to Charlottesville and Monticello. Owners Bill and Cynthia were ever gracious and so friendly. Highly recommend this perfect hideaway retreat if you are looking in this area and do not need to be in the heart of Charlottesville.
Stayed 4 nights in Jul 2020

10/10 Excellent

Prabhjot S.

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

Peaceful

Very nice experience. Good for families with children. Great hosts.
Stayed 3 nights in Jun 2022

10/10 Excellent

Martin W.

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

July 4th

We had a class reunion at my house this July 4th, and our guests stayed at the farmhouse. The host was very nice and gave us a tour of the property. The rooms were very clean and full of character. The kids really enjoyed the farm experience, including feeding the chickens and goats, and collecting eggs.
Stayed 2 nights in Jul 2024

10/10 Excellent

Laura m.

perfection!

This house is awesome-beautifully maintained, well stocked , picturesque setting. Great location-out of the way but still close enough in. Fit my family's needs perfectly. Lots of space inside and out. I highly recommend it and would definitely stay there again.
Stayed 2 nights in May 2018

10/10 Excellent

Roy C.

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

Great Weekend Stay

Six adults and two children enjoyed a wonderful holiday weekend at Quarters Farm. The setting provided lovely views across the countryside and all enjoyed the historic property and its surroundings. The children were able to help with feeding the goats and chickens making it extra special. We all left feeling relaxed and appreciative of the time we spent there. Our hosts, Bill and Cynthia were most welcoming and helpful, and ensured the children also had a memorable time. We all agreed it was a setting and weekend to remember!
Stayed 3 nights in May 2024

10/10 Excellent

Kathryn H.

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

anniversary/wedding

We had a total of 8 adults stay at this site, to celebrate parent's anniversary, as well as family wedding in the area. What a wonderful location and home!!! The owners are great, love their home and love sharing it with others. We had a relaxing time with adult children, with plenty of space for private conversations as well as for all of us together in the same room. The home is well stocked, including coffee and eggs: the furnishings are beautiful, plus decorated for Christmas, and very clean. We were all pleasantly surprised and thrilled with the quality of this home: it is the best we have experienced in a rental home.
Stayed 3 nights in Dec 2024

10/10 Excellent

Verified traveller

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

Family friendly fun and relaxation

We had a wonderful stay at Quarters Farm. The historic house is roomy and had everything we needed. The setting is peaceful and the view was great. Hosts are friendly and helpful without being intrusive. Had a ton of patience for our kids! They definitely didn’t get bored. Farm fresh eggs and produce were delightful. Would highly recommend!
Stayed 3 nights in Jul 2020

8/10 Good

Rose J.

Gorgeous location, house with wonderful character, and outstanding hosts.

The kids loved it, this is a great spot close / short drive to Charlottesville, apple picking spots, Monticello, and great hiking. There is a beautiful pond on the property across the road and the fishing there was so fun for everyone. The McCaskills are outstanding hosts, there were fresh flowers in practically every room and they let our son get eggs out of the chicken coop etc. He already wants to come back. If you are looking for a relaxing spot near to Charlottesville that is family friendly, you cannot go wrong here.
Stayed 7 nights in Oct 2018

10/10 Excellent

Caroline H.

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

Serene Living

Our hosts were wonderful and readily available to us. The beds were comfy, the air conditioning did a great job keeping us all cool and comfortable. There was plenty of space for the 8 of us. We couldn't have found a better place for a weekend reunion! Bill and Cynthia provided us with farm fresh eggs, which we enjoyed on the enclosed porch looking out over cows, chickens, and goats roaming the pastures. Kitten Hemingway and their Great Pyrenees Zoe kept us entertained when we were at the house and not exploring. Perfect vacation spot! Everyone was happy! Thank you to our hosts! They're amazing!
Stayed 3 nights in Sep 2023

10/10 Excellent

Stacy C.

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

Top Notch, A+++ all around experience

Where to begin? EVERYTHING about our experience at Quarters Farm was top notch! From their initial welcome message when we first booked the property, Bill and Cynthia proved to be warm and welcoming hosts. They guided us through the night and gave us a personal tour upon arrival, filled with fun historical facts about the home and property, fresh cut flowers, and delicious farm fresh eggs. The home itself is absolutely beautiful and was right up our alley with its historical bones and farm animals abound. We were in town for a family wedding (just a hop, skip and jump from the church and venue) and those family members who came to visit us at the property afterwards were all jealous of our lodging. So much so, we are plotting a family reunion and hope to stay at Quarters Farm again!
Stayed 3 nights in Aug 2023

10/10 Excellent

Russell B.

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

Perfect Country Getaway!

Our family of six stayed for three days at Quarters Farm. We were looking for a low-key, family friendly way to get away from the D.C. grind and celebrate our wedding anniversary. Quarters Farm was just perfect!! The house is clean and comfortable and has a very cool history. There is a wonderful view of a rolling hillside/mountain from the porch, and at night we were able to see the Milky Way and shooting stars. The farm has a small lake, and Bill had fishing equipment available -- we caught a few! The farm is also just a short drive from mountain hikes, UVA, and Monticello. The best part of the farm was the people though -- Bill and Cynthia are wonderful, thoughtful, down-to-earth, hospitable hosts who really made our stay special. They knew the kids' names, they showed us around the farm and greenhouse, and they let the kids hold baby chicks. Our three older kids (ages 6, 4, and 2) absolutely loved helping Bill with his "chores" -- collecting farm-fresh eggs (which were delicious for breakfast!), feeding the chickens, and feeding the goats. We can't wait to go back! Thank you, Bill and Cynthia, for sharing this treasure with us!
Stayed 3 nights in Aug 2020

10/10 Excellent

Christy T.

Quintessential Virginia farmhouse!!

We had extended family(8) there for my son’s wedding at Mount Ida farm. Absolutely loved everything about it!!!! My Florida family was just thrilled. Plenty of room. Easy access to I 64. Grocery Pizza , Thai food close by . I have att, one bar, so texting good. But difficult calls. WiFi there but very slow. So be prepared if business or easy communication on att is crucial. We managed just fine, but frustrating at times. We were there for a wedding at Mount Ida farm. Distance was fine. But these are country roads. GPS worked well enough, but took us on some really odd routes. Get written accurate directions if you are headed to any of the vineyards or country wedding venues. Can’t say enough about the hospitality from the owners, Bill and Cynthia..just fantastic! The house was comfortable, spotless with fresh cut flowers throughout!! I was up at dawn every day and enjoyed sitting on the screened in porch with my coffee. I really hope to make it back for another long weekend.. one where I can just relax!
Stayed 3 nights in Jun 2018

10/10 Excellent

Karla M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The kitchen was well stocked with good number of dinnerware, utensils, and everyday needed appliances.
Stayed 2 nights in Oct 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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