The Inn At the Crossroads by Pippin Hill Vineyard

5010 Plank Road , Charlottesville, VA 22959 USA (Show map)
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The Inn opened in 1820 and is a National Historic Register property and designated as a Virginia Historic Landmark. Just a 3 minute walk to Pippin Hill Farm and Vineyard, the Inn is located between Loving Cup Organic Vineyard and Albemarle Ciderworks. By car it is 9 minutes to UVA, 15 minutes to Monticello and under 20 to the Blue Ridge Parkway and Skyline Drive. From the Inn and vineyard, guests enjoy magnificent panoramic views of the Blue Ridge Mountains. Separate from the main building, the Summer Kitchen cottage offers guests that honeymoon-like escape. The cottage was originally the summer kitchen for the Inn and has been restored to a quaint two room guest house. The Inn is located in the center of the Monticello Wine Trail and near the northern end of the Brew Ridge Trail.




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  • Guest room4.4
  • Service4.7
  • Value4.4
  • Cleanliness4.5
  • Onsite Dining4.6

Great experience

5 on April 19, 2018

This place was such a good find. The rooms are beautiful and Jim and Janet were so nice and accommodating. Definitely going to stay here again.

A Walk through History

5 on April 17, 2018

We loved staying at the Crossroads B&B, if felt not only like we were see history but we were getting to be a part of it. Our footsteps were where some great members of our countries history had walked. I hope to stay there again.

Charlottesville stay

4.6 on April 12, 2018

Brief evening stay and departure early the next morning before breakfast, so we missed out on that meal. But the owner arranged for a "go bag" with coffee, scones and fruit so we were able to snack as we deprted

Wonderful getaway

5 on December 27, 2017

This place is beautiful and rustic. The owners are super friendly. This was our first stay and we plan on coming back every year!

Step back in Time

5 on September 09, 2015

We stayed in the Small Bldg across from the Inn and I can't think of anything that could have made our experience any more perfect. Jim is an awesome host and the location is ideal for anything you might want to do in this area. You need to appreciate the historical nature of an old place to call this your "cup of tea", but for us it was pure heaven!!

Amazing Bed and Breakfast!

5 on April 12, 2015

My sisters, my nieces, my mom and myself recently stayed at the Inn for two nights April 9th and April 10th. We had a great time Jim and Janet were exceptional host. Breakfast each morning was great! The Inn was just beautiful! Two of the people in our group had never stayed at a Bed and Breakfast before now, I think that they make it a point of staying at them now. Thanks for making our stay so enjoyable. I would highly recommend "The Inn at the Crossroads" what a treat! loved your dog! Thanks again. Kelly and family.

An amazing adventure away

5 on February 25, 2015

Recently I took wife away here for the night. We stayed in the Summer Kitchen, which is separate from the main Inn, and loved it. As you enter on the first floor you can see the history in the bricks and walls, you walk into a comfortable sized room with a couch, chairs and stove. There is also a wet bar in that room. We enjoyed sitting on the couch watching the fire in the stove. Up the stairs is a good-sized bedroom and bathroom. We really enjoyed the character of the place and you could really feel the history in the room, as well as in the main in where breakfast is serviced. The meal was outstanding and innkeepers were really knowledgeable of the inn and all the things that have happened there. You can tell they really do enjoy caring for the Inn and meeting new people. Now there is no TV and it allows the history to really shine, but there is Wi-Fi, so we streamed a movie on our iPad as we went to bed. We are fans of trying a different place everything we go somewhere, but I can say we would have to stay here again.

A great find!

4.6 on January 20, 2015

We stayed for two nights in the Dabney Carr room and thought this charming, rustic home was the perfect way to get into the historical spirit of the region. It was remote enough to feel like you were "getting out of town," but close enough to Charlottesville to explore the excellent restaurants and bar scene there. The owners were very friendly and had great tips on things to do, wineries to explore, restaurants to try, etc. It's a perfect place for history buffs and anyone looking for a cozy base to go wine tasting. Perfect for a "getaway" weekend.

Fantastic experience, we didn't want to leave!

5 on October 28, 2014

Everything about this Inn was perfect. We stayed in the Americana Suite which had great decor and history to it. The room was just about spotless. The innkeepers provided phenomenal service and breakfast was delicious! This Inn will not disappoint.


4.8 on September 01, 2014

An excellent spot just outside of town. Close to several vineyards and Monticello. Within walking distance of pippin hill vineyards which has a fantastic view. The house is a gem. Breakfast was fantastic. Would highly recommend it

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Rooms & Rates

Dabney Carr

Queen bed, private bath, wireless Internet. Named for the builder of the Inn, Thomas Jefferson's Nephew Dabney Carr. This room hosted a meeting between This room hosted a meeting between Thomas Jefferson and Martin Van Buren in 1823. This room has a lock of Abraham Lincoln's hair and a piece of his funerary flag, Secretary of State Martin Van Buren's 1823 guest book signature and an 1836 slave deed. To book with children or more than double occupancy see our website for suites and cottages.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $119 - $199

Sarah Gillocke

Queen bed, private bath, wireless Internet. This room is named for the woman who taught school in the Inn from 1820 until 1836, when the 1785 Anglican Church on the property was converted into a schoolhouse. To book with children or more than double occupancy see our website for suites and cottages.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $119 - $199

Mary Sutherland

Queen bed, private bath, mountain views, wireless Internet. Named for the wife of the first Innkeeper. Mary Sutherland had 16 children over 21 years, including two born in the same year, one in January and one in December. To book with children or more than double occupancy see our website for suites and cottages.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $119 - $229

Tavernkeepers Suite

Suite with King bed, private bath, 2 person spa shower, wireless Internet. This was the room used by Theodore Roosevelt in 1905, 1906, 1907 and 1908 and by Franklin Roosevelt in 1936. We have had a guest stay with us that was here for FDR's speech on the front porch in 1936 as an 8 year old boy.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King , 1 Queen

Nightly Rate: $129 - $299

Summer Kitchen Cottage

1824 Kitchen for the main Inn converted into a very private two story cottage. Queen bed upstairs, queen futon downstairs. The cottage has a working woodstove fireplace, private deck and full spa bath with bench seating. The Summer Kitchen Cottage is our only room that can accept children of any age.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen , 1 Double

Nightly Rate: $129 - $349

Americana Suite

Suite with King bed, private bath, mountain views from living room, shower with bench seat, wireless Internet. This room contains over a dozen artifacts, including a lock of Abraham Lincoln's hair and a piece of his funerary flag, George Washington memorabilia, a chair cushion from the Eisenhower White House and many more.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $129 - $289

Check Dates


Location Type

Countryside, Mountains, Small town, Wine country


Charlottesville, VA (CHO-Charlottesville-Albemarle) 20 miles

Directions to property:

From I-64 take Rt 29 south exactly 8.5 miles. Turn right on Rt 692. Inn is the second driveway on right. Only ten minutes to UVA's Scott Stadium and fifteen minutes to Monticello.

Area Attractions

Antique Shopping, Aquarium, Art Galleries, Concert venue, Eco-tourism, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Night life, Blue Ridge Parkway/Skyline Drive, Monticello, 20 vineyards, University of Virginia, Pippen Hill Farm and Vineyard, Albemarle Ciderworks, Loving Cup Organic Vineyard, Performing Theater, Picnic area, Religious Services, River, Ruins, Ski area, Tours, University, Vineyard, Winery

Inn Details

Establishment type

Other, Cottage, Historic Inn

On-site amenities

Board games, Coffee/Tea facilities, Conference Rooms, Library, Parking, Private entrance, Telephone, Washer/dryer, Wedding Facilities

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Fireplace, Fridge, Hairdryer, Ironing Board, Radio, Wi-Fi

On-site activities

Canoeing, Cross-country ski trails, Downhill Skiing, Fishing, Golfing, Hiking trails, Horseback riding, Mountain Bike trails, Shopping, Sight-seeing, Swimming, Tennis courts

Check Dates


  • Check In:: 4:00 PM
  • Check Out:: 11:00 AM
  • Open All Year Round: Yes
  • Smoking Allowed: Outside only Outdoors
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Limited Summer Kitchen Cottage only.
  • Childcare Provided: Limited Babysitting available
  • Guest Pets Allowed: No
  • Disabled Access Limited

Terms and Conditions



Jim and Janet Stern

Languages spoken


Resident Pets

About the innkeepers

Jim was formerly with Bed Bath & Beyond IT and Janet was a Chemist for BASF; both are former antique mall owners and historic home restorers. Jim is former military. Jim and Janet have turned their attention to this wonderful early 19th century tavern. They have owned and maintained this National Historic Register property and designated Virginia Historic Landmark since 2002.

Check Dates




  • Time Served: 8:30
  • Serving Location: Dining Room

Special meal options

Low fat , Restrictive , Vegetarian

Signature Dish

Baked Apple Pancake
Made with apples, peaches or pears from the Inn's orchard when available, this dish is reminiscent of a dish served during the Jeffersonian time period.