Ben Coolyn Farm | Architectural Digest Featured Vineyard Estate 6 Miles from Downtown Charlottesville

Elegant Estate in Keswick

  12 guests
  6 bedrooms
  6 full bathrooms
  Has Pool
  7800 sq. ft.

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Property Features

Sleeping Arrangement

Bedroom 1
1 King
Bedroom 2
1 King
Bedroom 3
1 King
Bedroom 4
1 Queen
Bedroom 5
2 Twins
Bedroom 6
2 Twins


We are excited to offer the exquisite Ben Coolyn Farm Estate to Stay Charlottesville's Premiere Property portfolio. 

As seen in  Architectural Digest, Virginia Living, and featured annually in Virginia Garden Week, Ben Coolyn Farm is steeped in old Virginia history and style. This 144 acre estate sits atop rolling hills with views that inspire year-round. While the historic nature of this 1870s Federal Style stately retreat has been impeccably preserved, you will also enjoy all of the warmth and comfortability that you would expect of a well-appointed home. The delicate elegance throughout every room is only further accentuated by the sweeping views of the surrounding landscape. Whether entertaining indoors or strolling the outdoors to marvel at the pastoral setting, Ben Coolyn is sure to impress even the most discerning traveler.

Enter the gates to the property and follow the tree-lined drive that leads you straight to the front entrance loop. An additional parking area is included to the right side of the home, ideal for larger groups. Breathe in the country air to begin your relaxing getaway at this bucolic retreat while admiring the formal gardens encompassing the house. The immaculately maintained grounds and the spectacular views of the farm and vineyard provide the perfect backdrop for making memories with your friends and family during your stay at this idyllic estate. 

Each of the home's five guest rooms exhibit a unique personality filled with elements of historic Virginian design. With three en suite baths and one shared hall bath for two of the bedrooms, your guests will enjoy the privacy they would expect from a modern hotel during their stay. Awake refreshed from a comfortable slumber and leisurely descend down one of the two staircases to make your way to the solarium for a relaxing start to your day; savor your morning coffee while the sun streams through the wall-to-wall French doors and windows.

If you enjoy entertaining you will love the ample seating in the expansive living room, anchored by a wood grand piano in the far corner. It is the perfect spot to gather with hor d'oeuvres and an aperitif while one of the area's private chefs is busy preparing a locally-sourced, three-course meal in the kitchen. As dinnertime approaches, be sure to appreciate the curated selection of artwork as you exit the living room and move across the hallway into the spacious formal dining room that is set to host your dinner party.

Behind the house you will see more beautifully tended gardens, including a greenhouse, a private pool and pool house, and captivating views of the vineyards and pastures. With the rolling hills as your backdrop, enjoy the pool with your group during the summer months.The pool house is its own separate dwelling, featuring a living room, full bathroom, and kitchen on the main level. A set of stairs take you up to the pool house bedroom which is a great additional sleeping space that could be used as a "honeymoon" cottage or anyone seeking their own retreat. 

Located just 6 miles from downtown Charlottesville and the University of Virginia, Ben Coolyn Farm is perfectly situated to provide you and your guests with the seclusion of a vineyard estate property while maintaining easy access to the area's many amenities. Keswick Hall, Castle Hill Cider and Keswick Vineyards are all located in the surrounding area. The location of Ben Coolyn will grant you a one-of-a-kind experience, with just a short drive to activities both in the city and at the other nearby vineyards and attractions. 

First Floor:
  • Formal Living Room with Grand Piano
  • Formal Dining Room
  • Fully- Equipped kitchen with breakfast area with views of the vineyard.
  • Study
  • Half Bathroom
  • Solarium
  • TV Room
  • Viking Gas 4 Burner Stove and Oven
  • Wine Fridge
  • Standard Drip Coffee Maker
  • Gas Grill
  • Washer/Dryer

Second Floor:

  • 5 Bedrooms, 4 Baths
  • Two King Bedrooms with En Suite Bathrooms
  • 1 King Bedroom with Shared Hallway Bathroom
  • 1 Twin Bedroom with En Suite Bathroom
  • 1 Queen Bedroom with Shared Hallway Bathroom
  • Balcony With Vineyard and Mountain Views


  • Outdoor Swimming Pool (weather dependent & subject to change: open May - September)
  • Outdoor Covered Gazebo
  • Pool House Cottage with Full Bathroom, Kitchen, and Upstairs Bedroom with Three Twins
  • Elegant Greenhouse with surrounding gardens
  • Children's Swingset 
  • Plenty of Parking
  • Tesla Charger
  • Whole House Generator

All guests of Stay Charlottesville receive exclusive access to Common House during your stay. Common House is a local membership based social club that offers a unique space to work, dine, and engage. There is a co-work space available during weekdays, a full service restaurant offering breakfast, lunch, and dinner as well as a roof-top terrace with sweeping views of Charlottesville.  

Read about Ben Coolyn Farm by clicking on the image below


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Stay Charlottesville Management Group:
Private Chefs | Private Yoga | Private Wine Tours | Concierge Services | Event Planning | 55 + Vacation Homes and Estates  


New York, US
Reviewed: September 7, 2019
1 2 3 4 5
I had one of the best weekends of my life at Ben Coolyn. Several of my best friends and their partners came down from New York. We'd planned to tour around the area, stopping at various vineyards and breweries, some historical sites, etc., but we never ended up leaving Ben Coolyn at all - none of us wanted to.
The property is vast, private, and completely delightful - imagine having Central Park entirely to yourself. There are three ponds, a vineyard, undisturbed mountain views, formal gardens, gorgeously maintained outbuildings, and the most perfect saltwater pool.
The house itself is incredible. You really can't get a feel for the scale of it until you walk in the front door. From the ballroom-sized living room, to the little library, the conservatory, and the incredible kitchen, the house is sprawling, beautifully decorated, and has many areas to enjoy. The bedrooms are enormous and very comfortable, with beautiful views from each window.
On our last morning, I woke up early, got a cup of coffee, and sat on the second-story balcony to watch the sun rise. There was mist rising over the pond, and the mountains beyond were glowing pink. It was really difficult to leave. Staying at Ben Coolyn is like having a private resort to yourself. It has everything you could want or need. We all left feeling relaxed and rejuvenated, and we can't wait visit again.
California, US
Reviewed: August 2, 2019
1 2 3 4 5
Ben Coolyn was the perfect location for our Girl’s Weekend in Keswick. The experience was truly one of a kind, from the moment we turned onto the driveway. The setting is pristine: ponds, endless hills, backdrops of vineyards and mountains. The house is surrounded by beautiful gardens, perfect for having a seat on one of the benches to relax and enjoy a glass of wine. The home itself is stunning: beautiful and designed impeccably, yet also completely comfortable and functional. Our beds were cozy and it was so serene waking up to the views framed by the windows. It is as beautiful, if not more so, than the pictures, with literally everything you need. Once you arrive at Ben Coolyn, you don’t really have to have a reason to leave - the entire property made us feel like being home except much, much better. Although we all live close by, the tranquility is like being in your own little world, very far removed from the hustle and bustle. Our favorite things were strolling the property, relaxing by the pool (perfect vineyard and mountain backdrop), and exploring the gardens. We cannot wait to do it again and plan on sharing this property with anyone we know that is looking to have a totally unbelievable Charlottesville experience!
Richmond, US
Reviewed: September 5, 2019
1 2 3 4 5
Ben Coolyn captured in only a headline would be, 'Picturesque Country Manner fit for the Queen's Court!’ Truly, the house and property are serene. Our low-key weekend away with family and friends was transformed into a dream-like experience! Every day there if felt like there was a new piece of the property or portion of the house we had yet to explore!
The house met out every need and the property is very kid-friendly. Our children were able to run and explore the grounds while the adults maintained peace of mind, relaxing by the pool, that they were safe. It reminded me of the type of freedom we had as kids! The fully equipped kitchen allowed for family meals in the spacious dinning room. It was the first time the kids didn’t even mention the word TV or go to grab the iPAD, which is quite a feat!
We are already looking at the calendar to return next year!


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San Jose, US
Reviewed: Oct 25, 2021
We got to see the amazing Foxhunt from our front yard...
Fairfax, US
Reviewed: Oct 18, 2021
Fantastic views, beautiful home, lovely walks on the property
Keswick, US
Reviewed: Jul 25, 2021
Ben Coolyn is a wonderful, historic home with the room and amenities for a relaxing family vacation. It came with everything our family needed to entertain the grandkids from ages 3 to 14 along with their parents and grandparents. Even though most of the family lives in the local area, we had a super time enjoying the beautiful, relaxing setting and Ben Coolyn's extremely classy home.