Home > Virginia B&Bs > Orange Bed and Breakfast Inns > Chestnut Hill B&B Inn

236 Caroline Street, Orange, VA 22960, USA    
(540) 661-0430


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5 based on 3 reviews
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Troy Ayers, Kathleen Ayers

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Circa 1860. Be surrounded by three acres of peaceful luxury. Meticulously landscaped and maintained, the front formal gardens boast a cascading fountain. Chestnut Hill B&B in Orange, Virginia was built as an Italianate Greek Revival that evolved into a Second Empire style. An extensive six-year renovation was recently completed and the bed and breakfast has been professionally decorated with period furnishings. Feel pampered by the evening turndown service then enjoy a restful night's sleep. In the morning, gather for a satisfying breakfast that includes fresh fruit, superior quality cuts of meat and a variety of gourmet dishes made with free-range eggs, Explore the scenic area and historic sites nearby.

For more information visit the website.


This property has 6 total guest accommodations with private bath, 1 with fireplace, 2 with hot tubs, 1 suite. The types of beds available include Double and Queen.

  • Air Conditioning
  • Bath Amenities
  • Bathrobes
  • Cable TV
  • Computers
  • Copy Machine
  • Fax
  • Hair Dryer
  • Handicap Access
  • Iron/Ironing Board
  • Television
  • Turn-Down Service
  • Wireless Internet Access

Business Traveler Amenities

  • Wireless Internet Access
  • Iron/Ironing Board
  • Modem Connection
  • Flexible Cancellation
  • Television
  • Desk
  • Flexible Check in/out Times
  • FAX On-site
  • Gym Nearby
  • Internet Access
  • Off-site Dry Cleaning Services
  • Hair Dryer

Events Hosted

    • Weddings
    • Seminars
    • Romantic Getaways
    • Meetings
    • Family Reunions
    • Honeymoons

Spa Services

On-Site Spa Services

  • Facials
  • Hair Care
  • Manicures/Pedicures
  • Massages
  • Waxing

Inns Of Interest

    • Civil War
    • Farms and Orchards
    • National Historic Register
    • Plantations
    • Train Stations & Renovated Rail Cars

Pet Restrictions

One room available for pets.
  • Pets Allowed
  • Innkeepers pets on premises
  • One Room Available For Pets

Romantic Interest

Bridal Suite was designed and decorated for romance. Be surrounded with pure luxury, comfort and uncompromised service at every corner with only the finest of furnishings and delicate bridal décor. Overlooking the front formal gardens and cascading fountain with a view of the quaint town of Orange.

Innkeepers Association Memberships

Paii, BBAV, Inns at Montpelier

Describe Garden and Grounds

Our 3 acres are professionally maintained and well manicured.

Reservation/Cancellation Policies:

Minimum Stay Requirements

Two-night minimum on weekends and holidays


Deposits are refundable on cancellations made at least 10 days prior to arrival. Deposits are non-refundable on any cancellation made less than 10 days prior to arrival.


Outside Only.

Other Activities

    • Horseback Riding
    • Hiking
    • Fishing
    • Canoeing/Kayaking
    • Bicycling
    • Art Galleries
    • Antiquing
    • Parks
    • Shopping (Local Crafts)
    • Wineries
    • James Madison's Montpelier
    • Civil War Monuments
    • Lake Anna

Historic Interest

Built ca. 1860 as a fashionable Italianate/Greek Revival dwelling for local businessman and politician Alexander Daley. Chestnut Hill is one of only a dozen residences in the town to survive from the antebellum era and is one of the best preserved of these dwellings. In 1883, Daley sold the property to Reuben Conway Macon, a Civil War veteran, great-nephew of President James Madison.

Historic Awards:

  • National Historical Site (Applied)
  • State Register (Granted)
  • National Register (Granted)
  • City Historical Site (Granted)
  • Local Register (Granted)

Historic Memberships:

  • City Historical Society
  • Local Historical Society

Historic sites nearby:

James Madison's Home - Montpelier (4 Miles), Thomas Jefferson's Home - Monticello (30 Miles), James Monroe's Home - Ashlawn (32 Miles), Wilderness Civil War Battlefield & Exhibit Shelter (20 Miles), Fredericksburg National Military Park & Visitors Center with Museum (35 Miles), Exchange Hotel Civil War Museum - Gordonsville (9 Miles)

Nearby College/University

University of Virginia

Write a review

My new favorite bed and breakfast!!

My husband and I had an amazing weekend with Kathleen and Troy!! David and I had a wonderful visit in your beautiful B&B! I have been to many B&Bs over the last 20 years and this is certainly the most luxurious and comfortable. Kathleen and Troy really go out of their way to make you feel at home and make you feel like royalty. The house is beautifully furnished and with luxurious linens, meals and furnishings! Breakfast was outstanding and they even made arrangements for David's picky palate! We will definitely be back to see our new friends!
Janice Ezzell

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Hosts with Open Arms

When we travel, we always stay in a bed and breakfast, however, none have been as nice as Chestnut Hill. As soon as we turned into the driveway and saw this beautiful house, we knew we were in for a treat and we have not been disappointed. The hosts welcomed us with open arms, shared the history of the house and their love for making it the wonderful place it is today. The rooms are well appointed, beautiful linens adorn the beds, the food was plentiful and delicious and the hospitality was out of this world! They met our every need from making our dinner reservations, suggesting places for us to visit and then spending time to make sure we had directions to our destination and even their cell phone number should we need it. After a day of sightseeing, they welcomed us back with a hot cup of coffee, dessert and great conversation. They have truly made our "48th" Anniversary special. We consider them as part of our family.
Stacy Lee

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

Better than the Savoy in London

My wife and I have stayed in some of the world's most luxurious hotels, including the iconic Savoy in London and the cushy Sofitel in Manhattan. None can compare with the lavish luxury, attention to detail and customer service as the Chestnut Hill Bed & Breakfast. Yes, I paid a little more than the average B&B to celebrate our 24th wedding celebration, but consider what I got: champagne and chocolates in the room, a free upgrade to the Bridal Suite, Beef Wellington for “hors d'oeuvres,” Kathleen's amazing skydiving video (optional) and Troy's passion for cooking and pleasing his guests (he called me three times -- including one call when my cell phone went off in church -- to make sure everything would be perfect before we arrived). I give Chestnut Hill five stars for value. It is well worth the price! I would book now before the word gets out about this sparkling new diamond on Virginia's B&B landscape. We stayed only one night (Sunday) but what a memorable stay it was. p.s. to innkeeper Thank you for the inspiration as I start my own communications company, Mark O’Keefe Communications. If you can do it so well, maybe I can too!
Vicki Hulbert
Fredericksburg, VA

My ratings for this property      
BOTTOM LINE: I would stay here again.
Did you find this review helpful? Yes (0 votes)
This review is the subjective opinion of an iLoveInns.com user and not of iLoveInns.com or American Historic Inns, Inc.

At A Glance

3 Review(s)
100% would stay again
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