For a limited time only, book
our "Wine Lover's Dream" 
package and receive up to 
5 hours of 
limousine service included. 

 This package can be added to your room reservation by clicking on the "Packages" tab and selecting "Book Now" on the "Wine Lover's Dream" package.




2013 Top 10 US B&Bs

Traveler's Choice Winner

Best of the Mid-Atlantic


"The ebbs and flows of life present challenges and opportunities along our personal journeys. For us, 2009 presented a period of challenges with work, health and general economic stresses that had prevented us from our normal carefree R&R routine. Finding your Inn when we did was nothing more than fate & destiny. You were just what the doctor ordered to help bring calm and balance back into our lives. You afforded us beautiful surroundings, bountiful amounts of great food and most importantly, new friendships that we will value into the future. Although we were here for a short visit, you offered us comfort like a sip of cool water on a hot day. Thank you! We look forward to our next visit."

With warmest regards,
Evette & Greta, Richmond, Virginia

I have been blessed to travel all over the world and stay at amazing hotels, eat great food and have experiences that a person from central PA would never have thought possible. Next to the Emirates Palace (literally a 7 star hotel) in Abu Dhabi, Chestnut Hill is the best place I have ever visited. You have to go there!

Todd & Julia
State College, PA

Imagine returning to the warmth, elegance, and luxury of the award-winning Chestnut Hill Bed & Breakfast, our bed and breakfast in Orange, Virginia after an exhilarating day exploring some of Virginia's most recognized vineyards, quaint shops, numerous historic sites, and monuments throughout Orange County including James Madison's Montpelier.

At this charming Charlottesville area bed and breakfast, share your experiences and get acquainted with your hosts and fellow guests during our evening wine & cheese event, wander down to our library and escape with a good book, or perhaps you need to finish that last-minute work in our business center.

Contemplate your next adventure while you enjoy a delightful gourmet breakfast, graciously served in the sun-drenched formal dining room or enjoy breakfast in bed in the privacy and comfort of your own quarters.

ABOUT Chestnut Hill Bed & Breakfast

The Inn at Chestnut Hill was built in 1860 by a local tanner named Alexander Daley, who was one of the founding members of the Town Council here in Orange, Virginia. The name Chestnut Hill came from the abundant Chestnut trees located on the property. Unfortunately, those trees were destroyed during the blight of 1910.

In 2003, the home was sold by way of absolute auction to Troy & Kathleen Ayers. One of the terms of the sale was that the new owners must move the house to an adjoining piece of property to make way for an access road to ease traffic congestion for the new Prospect Heights Middle School. With renovations finally complete, we are honored to announce that Chestnut Hill has been placed on Virginia's Register of Historic Places.

Upon your arrival at Chestnut Hill Bed & Breakfast, you'll immediately embrace the southern charm and welcoming greetings from the Innkeepers, Troy & Kathleen Ayers. Join them for a glass of wine from some of Virginia's award-winning wineries at our evening wine & cheese tasting before heading to dinner at one of the local restaurants. Or, just relax and unwind with an interesting book from our well-appointed library or watch a movie on the 62-inch plasma television in our entertainment area.

Chestnut Hill Bed & Breakfast Inn WeddingWire Winner 2017  2017 Best Places To Elope Winner


Trip Advisor Review Bed and Breafast Review
Weddings, Wedding VenuesChestnut Hill Bed & Breakfast Inn, Best Wedding Venues in Richmond - 2014 Couples' Choice Award Winner
Chestnut Hill Bed and Breakfast
236 Caroline Street
Orange, Virginia 22960
Chestnut Hill Bed and Breakfast Inn a Virginia Bed & Breakfast

© 2015 Chestnut Hill Bed & Breakfast Inn