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.  All this can be reality for you with a $250 gift certificate to Chestnut Hill Bed and Breakfast.  

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.

Included in night's stay:

• Full two-course gourmet breakfast served each morning


• Wine and cheese tasting each afternoon


• Turn-down service to include decadent chocolates


• Concierge service throughout your stay 

During your stay discover an underground world of wonder with personally guided tours for up to 4 people!

Shenandoah Caverns reveals its wonders along a one-mile tour circuit where a comfortable 56-degree temperature is maintained year-round. Plus, we offer the only cavern system with elevator service as well as the added convenience of level walkways and no stairs. So don't hesitate to plan your trip for explorers of every age and physical ability - everyone can enjoy the underground wonders at Shenandoah Caverns.

Shenandoah Caverns has thrilled visitors from around the world since it opened in 1922. Groups, families and people from all walks of life come to discover a world of breathtaking natural wonders, incredible geology and extraordinary crystalline formations waiting to be admired and photographed.

You'll see the famous "Breakfast Bacon" limestone formations, so unusual they appeared in National Geographic magazine. You'll be delighted by soaring rooms like Long View Hall. And you'll be amazed at the variety of unique, intricate and unexpected formations like Capitol Dome, Diamond Cascade and  Rainbow Lake.