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    Chester Bed & Breakfast

    5.0 (3 reviews)
    Open 7:00 am - 11:00 pm

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    11 years ago

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

    Orchard House Bed and Breakfast

    (30 reviews)

    We just discovered The Orchard House Bed & Breakfast in Lovingston, Virginia--only about 3 1/2…read morehours from Raleigh, NC--and it's the perfect getaway. The husband-and-wife owners, along with their four wonderful boys, are building such a special place here. The property is absolutely stunning: an amazing barn that's ready to host weddings, a sparkling pond with a fountain and gazebo, a vineyard right on-site, a beautiful swimming pool, a cozy fire pit, and breathtaking mountain views in every direction. There's so much to do--wineries, breweries, and incredible restaurants are just 15 to 20 minutes away in any direction, along with antique shops to explore. Or you can stay put and relax: enjoy a private breakfast on the front porch, book an in-room massage, or have a romantic dinner under the old oak tree in the backyard. And the breakfast? Out of this world. The wife is an incredible cook--you'll wake up to something better than you could imagine every morning. Whether you're looking for a quiet escape, planning a wedding, or just want to enjoy Virginia wine country, The Orchard House B&B is absolute perfection. Highly recommend!

    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.

    The White Pig Bed & Breakfast - A girl & a horse

    The White Pig Bed & Breakfast

    (33 reviews)

    My previous review disappeared ? Well, I've stayed a few times: once in the cloud cottage with my…read morehusband for our 20th anniversary, and later on the top level of the pink house, just myself and my teen&tween for girls' trip on my daughter's 14th birthday weekend. In a sentence, White Pig is a vegan bed-and-breakfast with Victorian aesthetic, where proceeds go directly to helping rescued pigs, goats, and horses. Both of our stays were incredibly enriching and meaningful to us as lifelong vegans. The rooms are extremely comfortable, elegant, tastefully and practically laid out. Heavy emphasis on pig related knickknacks, wall art, and general animal decor reminds you what is at the heart of all this. Founder/ owner/ innkeeper, Dina, is also chef extraordinaire. She provides gorgeous and nutritious vegan breakfast in a charming kitchen with cheerily arranged pig-forward table settings. As soon as you start talking with her, you'll find her to be one of the most compassionate advocates for animals you will ever meet. She's devoted her life to raising awareness and introducing people to the intelligent and gregarious animal so many of us grew up eating. Dina knows the area well and has wonderful suggestions. It's thanks to her that my husband and I took a hot air balloon ride over the Charlottesville Mountains during our anniversary stay. When I returned with my daughter's on our most recent visit, we opted to stay on the farm and visit with the resident rescues for the entirety of our leisure time. The horses and pony are located near the big house. My girls adored these social creatures who come to greet them over the fence. Then it was on to the pigs & goats. Oh my goodness there are domesticated pigs of every style and breed I thought imaginable, so many we had never heard of . Adorable kunekune (fury pigs), dignified little warthogs, standard English pigs with floppy ears, and every color and pattern a Vietnamese potbellied pig can be. For the most part the pigs are interested in a friendly hello. Some little fellows are standoffish and there's plenty of space for them to stay away from the commotion of visitors. There are quite a few goats in the mix as well. Each of these rescue animals are so delightful and it's humbling to think of the journeys that brought them to this beautiful vegan sanctuary. If you're looking to support a good cause while also being surrounded by natural beauty and staying in comfortable accommodations with a cruelty-free and quite delicious breakfast provided to you, then you should book a stay at White Pig. YES: VEGAN YES: kid friendly

    What a perfect stay we had at the White Pig B&B! It was the perfect December cozy atmosphere, the…read morewhole house is decorated to the nines with adorable farm and, of course, pig decor. It was a special touch that they shared the history of the pig our room was named after, along with a little bit of the sanctuary's story. Our room was beautiful and we were greeted with cupcakes when we arrived. They even went so far as to make a gluten free batch for my friend who called ahead of our stay to let them know. The vegan breakfast served was delicious! We had coffee, juice, grapefruit halves, an oven-baked omelet, apple turnover, and hash-browns. After breakfast we greeted and gave a few snacks to the horses, said hello and gave pets to all the miniature pot-bellies, and walked the gorgeous property. Overall, it was a unique getaway that we're already talking about doing again!

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

    Whispering Pine Plantation

    (2 reviews)

    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.

    Albemarle Estate - The dinner seating area.

    Albemarle Estate

    (39 reviews)

    $$$$

    We absolutely loved our one night stay at Albermarle Estate. Everything wasn't perfect of course,…read morebut we would definitely stay there again. When we finally decided on this hotel, mainly because it was halfway to our final destination of Pennsylvania, and it looked quite interesting, I had trouble booking through their webpage. Maybe you can blame it on me? I just couldn't quite get the system to accept the "check in--checkout" dates. So I gave them a call and booked through a representative located in Las Vegas Vegas. Everything went smoothly. She was very friendly and accommodating. We actually loved the curvy roads leading up to the winery and hotel. That portion of the trip would've been better in our roadster for sure! We were checked in by a friendly gentleman named Thomas. He gave us a room next to the outdoor pool. Finishings kind of reminded us a little bit of the accommodations. It was peacefully decorated, and mostly comfortable except for the couch. We were only using it to lounge in and something more comfortable would have been desirable. I took advantage of the dry sauna and hot tub, which was a short walk across the parking lot. We tried to take advantage of the grounds by walking around the small lake and through the fields. If they were in a dedicated walking trails, we didn't find them! We took a tour of the main house and enjoyed our French inspired continental breakfast, though croissants would've been a nice touch! The vistas from the winery and the hotel are quite spectacular! If you're looking for boutique or personalized lodging with beautiful surroundings, this may work for you!

    Very interesting place. At first, I thought about staying in a hotel, not too far away, just to…read morevisit the Trump winery. Yes, that would have worked, but I also would have missed the experience here. Being off season one cannot take in all the amenities like the pool, some of the outdoor activities, and just the ability to lounge or otherwise enjoy the surrounds while staying here. However, it still turned out to be a great experience. You need to pass through a double gate to get to the lobby. The first one would take you to the Trump Winery and the second one to the Estate itself. Yes, it is still a hotel, but it feels like a country club from start to finish. The place is small enough where they, for the most part, go off your name. Dinner reservation? Okay, here is your table. Done? There is no tab (or tip for that matter). Yes, you still need to pay for it, but it just goes on your room bill seamlessly. Want something? Just ask. From the tiny two-seat bar to anything else, service is pretty personal here. For dinner the ESTATE SALAD - Arcadian green mix topped with tomato, watermelon radish, goat cheese and golden beets dressed with Trump Blanc de Blanc vinaigrette, was amazing. My main of DUCK - Pan roasted medium-rare duck breast with cherry port wine sauce, honey glazed rainbow carrots, wild rice pilaf with estate grown herbs, was the best duck I have had in a very long time. Plus, having a flight of Trump wine (white in this case) gave me a preview of the winery I would get to tomorrow. The Viognier I found to be the surprise interest out of the four I tried.

    The Iris Inn

    The Iris Inn

    (187 reviews)

    $$

    We just spent the first few days of our honeymoon at the Iris Inn in Waynesboro - what an…read moreexceptional experience in every way , from the service, beauty and layout of the facilities, exceptional environment and personal attention paid by management and staff. We have already recommended The Iris Inn to friends and plan to return later in the fall of this year.

    What a hidden gem! I went to Iris as a solo getaway for the evening (last Thursday), traveling from…read moreNorthern VA (the concrete jungle) and stayed in Cabin #4. It was gorgeous. It was super clean, with a nice, cozy bed and comfortable, bougie amenities, including the shower you'd see at the St. Regis (open shower with a rain showerhead and sprayer). The private hot tub on the deck overlooking the mountains is gorgeous. I watched the sunset from my deck. I also discovered there's a washer/dryer in there in addition to a microwave and a fridge. So it's like a bougie version of a Residence Inn. Also, since I'm in my own cabin, I didn't hear anything from the outside unless I was outside. The property is beautiful. It has some small on-site hiking trails that take about 20-30 minutes. The clubhouse has an AMAZING chef-cooked breakfast in the morning that's included in your stay rate, and the on-site manager is so nice. They also put sparkling water and Fiji water in your fridge for free. You're also near the cute town of Staunton, which has gift shops, glass art (and glassblowing if you want to try), a historic railway, a high point city view (Sears Bridge), book shops, and restaurants/cafes. It's good to spend a few hours. There's no dinner on-site at the inn, but I went to the nearby Blue Mountain Brewery, which gets very popular. I hope you have a wonderful time here, and I HIGHLY recommend it.

    Chester Bed & Breakfast - hotels - Updated September 2026

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