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Chestnut Hill Bed & Breakfast

236 Caroline Street
Orange, VA 22960

Toll-free 888-315-3511

Phone 540-661-0403

EmailContact by Email

Imagine returning to the warmth and elegance of Chestnut Hill after an exhilarating day spent exploring some of Virginia’s most recognized vineyards, quaint shops and numerous historic sites and monuments throughout Orange County including James Madison’s Montpelier.

Built in 1860, Chestnut Hill, a bed and breakfast in Orange, VA, has been skillfully renovated to preserve the master craftsmanship of this renowned historic home and professionally decorated to provide our guests with an opportunity to appreciate the past while enjoying the comforts of the present. There are only two guest rooms per floor and each room offers a private bath with hairdryers, quality personal amenities, pillow-top beds dressed in triple-sheeted superior quality cotton linens, lush cozy spa robes, HD flat screen televisions and WiFi Internet access. Extra special touches may include fresh cut flowers, bottled flat or sparkling water and home-made tea-time treats & confections.

Our savory fusion breakfast, evening wine & cheese tasting, all day complimentary beverages and unparalleled customer service are always included during your stay at Chestnut Hill Bed & Breakfast.


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Over 12


Mountains, Small Town/Village


  • Free Onsite Parking
  • Gardens on Property
  • Business Center
  • GLBT Friendly
  • National Historic Registry


Outside Only


Wireless, Complimentary


Chestnut Hill Bed & Breakfast provides our guests with an opportunity to appreciate the past while enjoying the comforts of the present.  There are only two guest rooms per floor, and each room offers a private luxury bath with hairdryers, quality toiletries, pillow-top beds dressed in triple-sheeted superior quality cotton linens, lush cozy spa robes, HD flat-screen televisions, and Wi-Fi Internet access.  Two guestrooms feature hot tubs and fireplaces. Extra special touches may include fresh-cut flowers, bottled flat or sparkling water, and homemade tea-time treats & confections.

  • Non-Smoking Rooms
  • Suites

Double , Queen


Full ADA

  • Air Conditioning
  • Antique Furnishings
  • Bathrobes
  • Fireplaces
  • Hairdryers
  • Luxury Linens
  • Refrigerators
  • Rollaway Available
  • Whirlpool or Jacuzzi
  • Alarm Clocks
  • Ironing Boards
  • Turndown Service

  • Cable TV
  • iPod Docking Stations

More about our rooms

At our Virginia country inn, we take great pride in serving our guests the finest freshly made breakfast items daily. Each morning begins at 7:00 with fresh-roasted coffee as well as a wide selection of herbal and caffeinated teas. Prepare to treat yourself to a gourmet meal beginning with a fresh fruit entrée and our Homemade Gourmet Granola, and then follow it up with our hot entrée of the day.

Our entrées vary from "sweet one day to savory the next," sometimes a combination of each. Whether you join us at the main table or have a quiet meal at your own private table, breakfast at our luxury accommodation in Virginia becomes the best way to start your day.

We always have alternative breakfasts available such as hot or cold cereal, plain scrambled eggs, or plain French toast, so please let us know your preferences at check-in.



Individual Tables, Communal, Flexible Times


Beer, Wine, Spirits


  • Special Diets Accommodated
  • Vegetarian Options

  • Complimentary Beverages
  • Afternoon Tea/Refreshments
  • Complimentary Snacks
  • Early Coffee/Tea
  • Evening Cocktails
  • Evening Hors d'oeuvres
  • Picnics Available
  • Room Service


More about dining at our inn

  • Amusement Parks
  • Antique Shopping
  • Art Galleries
  • Biking
  • Boating
  • Canoeing/Kayaking
  • Culinary Classes
  • Fishing
  • Garden Tours
  • Golf
  • Hiking/Nature Trails
  • Historic Sites
  • Horseback Riding
  • Hot Air Ballooning
  • Hunting
  • Library
  • Museums
  • Rivers/Lakes
  • Shopping
  • Snow Skiing - Cross Country
  • Snow Skiing - Downhill
  • Sports Events
  • State/National Parks
  • Winery Tours

More on what to do at our inn

More info on our packages

  • Business
  • Family Reunion
  • Social

For those seeking an outstanding location for traditional, elegant Virginia weddings for up to 200 guests, Chestnut Hill Bed & Breakfast Inn is ideal.

We specialize in offering outdoor weddings in Virginia with a gracious style not readily found today, allowing friends and family to gather in a serene, country setting to celebrate your wedding day. Whether you desire a romantic elopement or a grand affair, we are at your service and equipped to assist you with every detail. Once you've had the opportunity to review the wedding packages and information, let us show you how we can help make your elegant country wedding a unique and memorable day filled with a beautiful setting, fine dining, and unparalleled customer service.

  • Ceremony
  • Receptions
  • Rehearsal Dinner
  • Bridal Luncheon

  • Outdoor


More about our weddings services

Check out the recipes on our website

Irish Potato Soup with Cheese and Red Ale

Red ale, leeks and Kerrygold Dubliner cheese make this soup uniquely Irish. Make it your own by adding crumbled blue cheese and/or bacon.