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Oak Grove Plantation Bed and Breakfast

Oak Grove Plantation Bed and Breakfast

The Oak Grove Plantation bed and breakfast is a 400-acre property located in the southern-Virginian town of South Boston. In addition to various hiking trails and outdoor amenities, the site contains two two-story buildings with a total of 5 units available to reserve. The bed and breakfast can trace its history over 200 years in the past and prior to the American civil war. The home that has expanded into the business that it is today started as a family residence and has gone through many changes throughout its history. Mary Pickett Craddock and Mike Doan, the owners, strive to create a laid-back atmosphere for the guests of the bed and breakfast. Oak Grove Plantation has received various reviews throughout its time of operation, with the quality of service and the food being commonly mentioned items in those reviews.


Found on the southern edge of Virginia, the Oak Grove Plantation Bed and Breakfast is a 400-acre property located in the town of South Boston, Virginia. The property is made up of two two-story buildings, as well as an exterior yard with various features. The first and main building is two-storied and contains two units available for rent: The Family Suite and The Library Room. The Family Suite is outfitted with two bedrooms, one of which is equipped with a queen-size bed, while the other contains two twin-size beds. The Library room is a single room that is outfitted with a single, queen-size bed. Two stories are found in the secondary building on the property and it contains two units with the capacity to house three parties. This house contains the tree house on the top floor, and the bottom floor contains the 1850 cottage. This cottage is made up of two separate units that can be reserved separately or jointly depending on the needs of the guests. Overall, these two buildings contain a maximum of 5 units that are available for reservation. 

Each of the rooms between both of the buildings on the property has unique furniture and decorations, giving patrons the ability to choose their own ambiance during their stay at the Oak Grove Plantation Bed and Breakfast. All of the rooms are also equipped with certain universal amenities, such as complimentary bathrobes, a ceiling fan available for guest use, an extra bed available that a room may use if the need arises, hair dryers in each of the bathrooms, ironing boards, and complimentary Wi-Fi. Both buildings are equipped with additional rooms that guests have access to during their stay at the bed and breakfast. The main building has a kitchen primarily used for cooking the complimentary breakfast, a dining room, and a parlor with legos and other toys for children to use. The secondary building has a kitchen that is solely for guest use. 

The Oak Grove Plantation Bed and Breakfast is located in a rural area of Virginia. Outside of the buildings, the property is decorated with pine trees and various hiking trails that patrons of the property are able to explore during their stay. Mary Pickett Craddock, one of the owners of the Oak Grove Plantation Bed and Breakfast, describes the property as "grassy with trees." In addition to the natural attractions of the property, there are various features that have been added to the area throughout the years. These features include a tire swing, sandbox, and a cemetery that guests can visit. 

A complimentary breakfast is served to every guest each morning at varying times between 7 and 10 a.m. Breakfast is served in the dining room, but guests have the freedom to choose to eat their meal in the dining room or outside at various tables that are set up for that purpose. Mary describes the breakfast as a "full breakfast with unique and common dishes alike." Additionally, guests who have specific dietary needs can reach out to Mary or the other owner, Mike Doan, and they state that they will strive to meet their needs for their breakfast.


Mary Pickett Craddock and Mike Doan, the owners of the Oak Grove bed and breakfast, strive to create an atmosphere at the bed and breakfast where "the pace is slower and the hospitality warm." In order to provide the guests with the experience that they desire, Mary and Mike have implemented various policies, developed habits as managers of the business, and provided multiple services that they believe will help them reach their goal for the culture of Oak Grove Plantation bed and breakfast. The policies that all guests are expected to follow include strict check-in and check-out times, regulations regarding which rooms are acceptable for dogs, and a ban on indoor smoking throughout most of the property. There is a designated area on the outdoor porch where guests are permitted to smoke if they so wish. 

Mary explains that both she and Mike enjoy interacting with the guests of the bed and breakfast. She says that they strive to develop a relationship with the patrons of the property in order to provide them with an experience that makes them want to come back. In addition, Mary provides guests with historical tours of the property as well as guided hikes through the trails on the property. Mary says that she loves doing both of these activities. Mike states that he is an avid jazz pianist and plays the piano in the parlor for the guests while they are using the room to relax. 

The Oak Grove Plantation bed and breakfast has received many reviews throughout its time of operation. One of the past guests of the property described their experience as such: "The breakfast was amazing each day. Oak Grove has so much land to explore. Easy trail walks and bird sightings. Not to mention that this home has over 200 years of history, and all are still within the same family!"


The main building on the property that is now the Oak Grove Plantation bed and breakfast was constructed in 1820, prior to the American civil war, by a tobacco farmer named Tomas Easley. Easley, who served as a member of the Virginia state legislature for a single term, built the home originally in the federalist style with two bedrooms for his family to live in. The property was a private residence and farm all throughout its history until 1988 when the property was converted into a bed and breakfast by Mary Pickett Craddock, the current owner of the property. 

Since its inception as a bed and breakfast, Mary Picket Craddock has made multiple renovations and changes to the property. These additions include two additional bathrooms, a handicap ramp, handrails on the exterior stairs, and central air conditioning and heating. In addition, solar panels were added in order to provide electricity throughout winter to the house in 2016. Originally, the property was solely a summertime bed and breakfast but was converted into a year-round bed and breakfast in 2020 due to Covid-19.  Craddock explains that she loves to cook and wants to show off the house to other people, and she further explains that these are the reasons that she started the bed and breakfast and also the things that she loves most about running it. 

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1245 Cluster Springs Road
South Boston, Virginia 24592
United States




Mary Pickett Craddock and Mike Doan

Owned Since
Has been in the Craddock family since 1853
5 (31 Reviews)
5/5 31 Reviews
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