We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
08/10/2017 09/10/2017
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}

    Chestnut Hill Bed & Breakfast Inn

    236 Caroline St, Orange, VA 22960-1541
    Hotel website
    Lowest prices for your stay
    08/10/2017 09/10/2017
    USD 216*
    USD 216*
    USD 216*
    Traveller (80)
    Room & Suite (16)
    Dining (5)
    • Excellent98%
    • Very good1%
    • Average0%
    • Poor1%
    • Terrible0%
    Travellers talk about
    “bridal suite” (18 reviews)
    “b b” (119 reviews)
    “the owners” (37 reviews)
    Free Wifi
    Free Parking
    Breakfast included
    Air Conditioning
    Non-Smoking Hotel
    Room Service
    3.5 Star Hotel
    All hotel details
    8 Oct.9 Oct.
    1 room, 2 adults, 0 children
    • Check booking site for details
      USD 216
      View Deal
    • Check booking site for details
      USD 216
      View Deal
    • Check booking site for details
      USD 216
      View Deal
    View all 30 deals
    Write a Review
    Reviews (313)
    There are newer reviews for Chestnut Hill Bed & Breakfast Inn
    See the most recent reviews
    Traveller rating
    Traveller type
    Time of year

    141 - 145 of 313 reviews

    Reviewed 2 June 2013

    We were in Orange for two nights in May. We did something unique for us - we stayed at two different B&B's. Both with nearly perfect TA ratings. Chestnut Hill was a 10-minute walk to downtown; the other Orange B&B was on a quiet wooded...More

    1  Thank Skip B
    Reviewed 5 May 2013

    First impressions are everything and Kathleen and Troy and their staff were amazing. Me and my fiance arrived about 2 hours early before our check in time and the staff gave us some wine and allowed us to sit outside and relax. They helped plan...More

    1  Thank sej w
    Reviewed 19 April 2013

    Other innkeepers are probably not very happy with Troy and Kathleen, the innkeepers and owners at Chestnut Hill. That's because they set a standard for excellence in innkeeping that most others will never be able to meet. Our experience began as soon as we reached...More

    1  Thank Tom B
    Reviewed 19 April 2013

    Oh! What a wonderful stay! The first thing when we arrived we were told they would up-grade our room. Each room is so different but beautifully decorated. Then the food – Oh my! Gourmet plus! Savory and sweet. I rate this 6 stars out of...More

    Thank CarrolB
    Reviewed 15 April 2013

    If you have never experienced Chestnut Hill B&B I suggest you look them up and book a room...now! I surprised my wife for our 10th year anniversary and Troy and Kathleen were awesome in helping me plan this secret getaway. I told my wife that...More

    Thank Proclame
    Comfort Inn & Suites Orange
    116 reviews
    #2 of 2 hotels in Orange
    Doubletree by Hilton Charlottesville
    1,383 reviews
    #12 of 35 hotels in Charlottesville
    Hampton Inn and Suites Charlottesville - At The University
    761 reviews
    #4 of 35 hotels in Charlottesville
    Boar's Head Resort
    938 reviews
    #8 of 35 hotels in Charlottesville
    Awards & Recognition
    Certificate of Excellence
    • Top amenities
    • Free Parking
    • Free High Speed Internet ( WiFi )
    • Breakfast included
    • Room Service
    • Hotel Amenities
    • Free Parking
    • Breakfast included
    • Room Service
    • Concierge
    • Room amenities
    • Air Conditioning
    • Price range
    • USD 194 - USD 293 (Based on Average Rates for a Standard Room)
    • Hotel class
    • Room types
    • Suites ,
    • Non-Smoking Rooms ,
    • Family Rooms
    • Number of rooms
    • 6
    • Reservation Options
    • TripAdvisor is proud to partner with Travelocity, Expedia, Hotels.com, Cancelon, Orbitz, Hotwire and Cheap Tickets so you can book your Chestnut Hill Bed & Breakfast Inn reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
    • Location
    • United States >
    • Virginia >
    • Orange
    Add Photo Photos
    Traveller (80)
    Room & Suite (16)
    Dining (5)
    Hotel & Grounds (73)
    Bathroom (5)
    Business Centre & Event Rooms (2)
    Hampton Inn and Suites Charlottesville - At The University
    761 reviews
    40.47 km away
    Doubletree by Hilton Charlottesville
    1,383 reviews
    34.26 km away
    Boar's Head Resort
    938 reviews
    43.00 km away
    Comfort Inn & Suites Orange
    116 reviews
    .39 km away
    Nearby Restaurants
    La Finca Grill
    237 reviews
    .62 km away
    Wise Guys
    113 reviews
    .77 km away
    The Light Well
    247 reviews
    .75 km away
    Silk Mill Grille
    253 reviews
    1.40 km away
    Nearby Attractions
    James Madison's Montpelier
    918 reviews
    5.82 km away
    James Madison Museum
    52 reviews
    .47 km away
    Honah Lee Winery
    49 reviews
    6.62 km away
    Skydive Orange
    37 reviews
    5.86 km away
    Ask a question
    Questions & Answers
    31 October 2014|
    AnswerShow all 3 answers
    Response from Terry M | Reviewed this property |
    I know that they have many weddings there... but I would not say it is secluded. It sits on a hill looking down to an intersection. It is however, very peaceful! There is horseback riding, vineyards, historical sights, and... More
    Room Tips
    "Each room has a theme and uniquely decorated. Each one perfect."
    Read review
    "We always try to stay in Ask Anna for the beautiful bathroom and Jacuzzi tub!"
    Read review
    "Every room was magnificent. The Bridal Suite is off the hook!"
    Read review
    "I was able to tour the Bridal Suite and it was AMAZING!!!"
    Read review
    Is This Your TripAdvisor Listing?
    Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more. Claim Your Listing