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    John & Olivia’s B&B

    5.0 (3 reviews)
    Open Open 24 hours

    John & Olivia’s B&B Photos

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    Orchard House Bed and Breakfast - Gorgeous and cozy BnB with a perfect porch

    Orchard House Bed and Breakfast

    4.7(30 reviews)
    9.4 mi

    An absolutely lovely inn. Top notch service. Beautiful inn. Fully renovated but maintains original…read morecharm. The food was amazing! Highly recommended for a romantic getaway, family reunion or more!

    We paid more than $500 to rent their event area. It was advertised as a nice, renovated area WITH…read moreAC and we were told it would be cleaned before our event. We were also told the owner/event manager would be on hand for help the day of. She seemed to forget who I was after meeting with me multiple times, but no biggie. I'm sure she meets lots of people. What was really not okay was that when we showed up to set up our event, the area was NOT cleaned and there was nobody to be found. There was dust and dirt everywhere that took an hour to clean before even being able to set up, a gross dead bug graveyard in the sitting area floor, it smelled musty, and overall was just not up to the standard they advertised. The owner nor any staff showed up at any point. We were not greeted, we were not helped, and it was just kind of a "okay good luck" situation. Also, the "AC" was on 75 on a hot May day. After paying the second half of the $550 fee, I didn't hear from the event manager other than a text asking what time I'd be in. Afterwards, nobody checked on us or the space. Never even heard from them to get a "thank you for renting our space" or "I'm sorry I wasn't available today"... To pay $550, you'd expect to get what you pay for. As a local, I will NOT be renting there for any other party I host nor trying out their B&B if the service is anything like this experience has been. Next time, we'll pay $550 for a nicer place on 151.

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    Orchard House Bed and Breakfast
    Orchard House Bed and Breakfast
    Orchard House Bed and Breakfast

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    Whispering Pine Plantation - A beautiful wedding day sunset for this incredible couple!

    Whispering Pine Plantation

    5.0(2 reviews)
    48.9 mi

    My fiancé and I booked our wedding shortly after we got engaged at Whispering Pines. It did not…read moreeven compare to other venues. It was the most affordable compared to other venues, most beautiful, and we have the luxury of staying the weekend and relaxing with our family! The house is amazing, and the soy crops outside mixed with the trees really sold it for us. Not only did we love the venue, but we also felt warm and welcomed by Annmarie. Since the moment we booked she has been a great communicator and we feel like she is really listening to our needs. Not the "corporate" feel if you will. We also did our save the dates at the venue with their photographer! They turned out AMAZING! It was so fun and taking pictures with the horses really made them feel so much more magical. We are booked for May and I could not be more excited! Also just to add- they had so many options to help with vendors, which helped us pick our caterer! It's so much less stress than I imagined because they are SO helpful! I am so excited about our wedding and could not recommend this venue enough!

    My husband and I stayed here for 2 nights after a wedding at another plantation down the road, and…read moreit was a great experience. We got a chance to enjoy the kitchen and the pool. Our room was nicely appointed and the bed comfortable. The bathroom was a nice size with good water pressure. They do not cook a full breakfast in the mornings but there were bagles cream, cheese, other pastries, coffee, tea, and juice for us in the morning. We never ran into the owner until just before leaving on the second day, but felt at home the whole time. We will definitly be back again the next time we are in the area, it is definitley a home away from home kind of place and was a great value for quality of accomodations. The only downfall is that it is cash or check only...no cc travel points for me on this stay.

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    Whispering Pine Plantation - Our first wedding elopement!

    Our first wedding elopement!

    Whispering Pine Plantation - Attention brides - spend the night before the big day with your gals and enjoy the beautiful bridal suite.  The home sleeps 22!

    Attention brides - spend the night before the big day with your gals and enjoy the beautiful bridal suite. The home sleeps 22!

    Whispering Pine Plantation - The moment when the groom first sees his bride................

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    The moment when the groom first sees his bride................

    Chester Bed & Breakfast - Built in 1847, Chester is a gracious B & B in the midst of historic sites and Virginia's wine country.

    Chester Bed & Breakfast

    5.0(3 reviews)
    11.0 mi
    $$$

    One review?!? People need to know about this place!!!…read more We travel frequently and love to stay at B&Bs. We had reservations to stay at a different B&B in Scottsville but due to an unfortunate situation we found ourselves looking for alternate arrangements. While I was on the cell phone checking for a place my wife ran across The Chester and called them. She was smiling from the moment that she spoke with them on the phone which, considering our frame of mind, was a great start. We got to this place which was absolutely gorgeous. The Inn was spacious, clean, very tastefully decorated and painted, and smelled like roses and family. We were warmly greeted by Jean who showed us the rooms and was accommodating from the get go. She helped us plan dinner and set up a late wine tasting trip, as well as offered to make dinner for us the evening after. The dinner was fantastic with Jean and Craig pampering us with delicious food, wine and dessert. If you have the opportunity to have dinner with them ask her for the orange squash soup and the rosemary pork...WOW! The breakfasts too were amazing!! We offered Jean to buy our own bacon/sausage since my wife does not eat nitrates (migraines). She told us not to worry about it and she will figure it out. The first day she served a fantastic veggie quiche (sorry if I am not using the right term) with fresh juice and french pressed coffee. The second day french toast with NITRATE FREE apple sausages! Our rooms were promptly made every day and Craig made sure to provide turned down service which was a very nice detail. Oh yeah, we got to meet the grand baby and also the Inn mascot, Trixie, who is a sweet little dog with the best personality. One of the best B&B experiences we've had period! We will be back!!

    We recently stayed at this historic B&B and had a wonderful time. The hosts (Craig, Jean & Trixie…read more(dog) couldn't have been more welcoming or hospitable. When we arrived we were greeted with a warm "Welcome, and consider yourselves part of the family"....and that is how it was. We chatted with the hosts at Breakfast (which was delicious) and when we returned from dinner in the evening. The second evening we even talked them into a scotch and great conversation in front of a roaring fire. Location is quaint and peaceful and very close to all of the sites you would want to visit (Monticello, Madison's house, wineries, Charlottesville, antique shops, etc.). A great stay.

    John & Olivia’s B&B - bedbreakfast - Updated July 2026

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