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.

“Great Getaway” 5 of 5 stars
Review of Chestnut Hill Bed & Breakfast Inn

Best prices for your stay
Enter dates for best prices
Check In mm/dd/yyyy Check Out mm/dd/yyyy
Show Prices
Compare best prices from top travel sites
and 4 more sites!
Save
You added Chestnut Hill Bed & Breakfast Inn to your Saves list
Chestnut Hill Bed & Breakfast Inn
3.5 of 5 Bed and Breakfast   |   236 Caroline Street, Orange, VA 22960   |  
  |  
Hotel website
  |  
  |  
Hotel amenities
Ranked #1 of 7 Orange B&B and Inns
Certificate of Excellence 2014
Waynesboro, Virginia
1 review
“Great Getaway”
5 of 5 stars Reviewed March 14, 2014

This inn is amazing...I was not aware of the history...what a story behind the sale of the property and the renovations of the house. The rooms are all beautifully decorated and supplied. We stayed in the Four Quarters Room. The bed was very comfy and we slept well. The bathroom was a bit small, but has all the necessaties. I am just used to one that is 3 times the size. The breakfast and afternoon hors d'oeuvres were scrumptious! The restaurants & wineries that we ventured to were excellent as well. Troy was very helpful with the recommendations and places to go. We had a wonderful experience and will definately want to return for a special occasion.

  • Stayed March 2014, traveled with friends
    • 4 of 5 stars Value
    • 4 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service

Review collected in partnership with this hotel

Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

238 reviews from our community

Traveler rating
    235
    3
    0
    0
    0
See reviews for
23
185
1
5
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (48)
Date | Rating
  • English first
  • Any
English first
Washington, District of Columbia, United States
Senior Reviewer
6 reviews 6 reviews
3 hotel reviews
Reviews in 5 cities Reviews in 5 cities
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed March 10, 2014

It was beautiful, comfortable, and absolutely lovely. The breakfasts were delicious. I cut my food into smaller and smaller bites just so it would last longer. Kathleen and Troy went out of their way to make us feel welcome and plan out our time in the area. My only complaint is that our stay was too short (2 nights). The bed was so comfortable I was reluctant to even leave the room. Before we arrived, we were surprised by the number of 5 star reviews. Now we get it. Nothing is left to chance. We arrived back late after a day of wine tastings, and Kathleen brought up the delicious happy hour snack we had missed. Expect luxury without the fussiness. Expect fantastic breakfasts and warm hosts. You won't be disappointed. We weren't.

Stayed March 2014, traveled as a couple
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Martinsville, Virginia
1 review
5 of 5 stars Reviewed March 6, 2014

Kathleen and Troy are such wonderful hosts. The rooms are all so cozy and beautiful but I stayed in Serendipity. What a wonderful room and the house is so full of history. I started the day off right with a gorgeous breakfast and a day of sight seeing that Troy mapped out for me. Everyone is so thoughtful, really you could ask for a better weekend.

  • Stayed February 2014
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Washington DC, District of Columbia
1 review
5 of 5 stars Reviewed January 20, 2014

From the time we drove up the long driveway to the House -- our stay was great. The room was wonderfully decorated with a very comfortable bed. The owners (Troy & Kathleen) and staff was immensely accomodating. The owners recommendations of restaurants and local activities was dead on. Really enjoyed the small town -- it was Norman Rockwellesque! Breakfast was delicious. Our stay was terribly relaxing and fun. Would recommend Chestnut Hill B&B to all.

Stayed January 2014, traveled as a couple
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Warwick, Rhode Island
Contributor
11 reviews 11 reviews
4 hotel reviews
Reviews in 8 cities Reviews in 8 cities
12 helpful votes 12 helpful votes
5 of 5 stars Reviewed January 19, 2014

From the moment we booked the trip, until we left, we couldn't have asked for better service, food and accommodations. Troy and Kathleen took care of us like we were close friends. Troy called us while on the road to provide us with a back roads route to avoid traffic to his establishment, and asked if we had any food allergies or special needs. Both were much appreciated questions, since the traffic was horrific on the main roads and my husband has a severe allergy to crabmeat.
Upon arrival, we were warmly received,helped with our luggage, and offered a wonderful cup of shrimp bisque and crab ( minus the crab) for my husband, plus an assortment of local wines, beer and soft drinks to choose from at no additional charge, in there tastefully appointed wine cellar.
Both Troy and Kathleen got it down. They are friendly, informative about where to dine, and things to do , without intruding on your privacy but always there to help you if needed. Actually, we would have to liked to spent more time with because they are both interesting people with similar taste. Most importantly in that regard, my husband and I consider ourselves to be "foodies", and Troy and Kathleen are amazing cooks.
There place is everything you would expect from a B&B- house is on the historical register, beautifully appointed, yet not stuffy, dated, or pretentious. I would recommend staying in the suite. Our room had a gas fire place in both the bedroom and bath, jacuzzi and shower, with all the bells and whistles, HD TV and WiFi - very private and comfortable.

  • Stayed January 2014, traveled as a couple
    • 5 of 5 stars Value
    • 4 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 2
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Dunedin, Florida
Reviewer
4 reviews 4 reviews
3 hotel reviews
Reviews in 4 cities Reviews in 4 cities
5 of 5 stars Reviewed January 4, 2014

Everything one would expect from a five star property and so much more. The host nd hostess, were beyond accomodating...they went the extra mile for everything. As a father traveling, hoping to make my wife, grandson and his girlfriend happy, I looked like a hero! The food was perfect, the rooms amazing and the grounds (in December) beautiful. I would recommend this to the most discriminating traveler.

Room Tip: There are no bad rooms!
See more room tips
  • Stayed December 2013, traveled on business
    • 5 of 5 stars Value
    • 4 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Chesapeake, Virginia
1 review
5 of 5 stars Reviewed January 1, 2014

Spent New Years Eve there. outstanding food greatest place ever. Everything about this place is outstanding. They go above and beyond what is expected. Kathleen and Troy . will help you make your stay the best you could ever imagine

  • Stayed December 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Hotels you might also like...
mm/dd/yyyy mm/dd/yyyy
Price Your Stay

Been to Chestnut Hill Bed & Breakfast Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Chestnut Hill Bed & Breakfast Inn

Address: 236 Caroline Street, Orange, VA 22960
Phone Number:
Location: United States > Virginia > Orange
Amenities:
Business Center with Internet Access Free Breakfast Room Service
Hotel Style:
Ranked #1 of 7 B&Bs / Inns in Orange
Price Range (Based on Average Rates): $$
Hotel Class:3.5 star — Chestnut Hill Bed & Breakfast Inn 3.5*
Number of rooms: 6
Official Description (provided by the hotel):
Built in 1860, Chestnut Hill 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 confections. ... more   less 
Reservation Options:
TripAdvisor is proud to partner with Expedia, Travelocity, Priceline, Orbitz, Hotwire and Hotels.com so you can book your Chestnut Hill Bed & Breakfast Inn reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.

Owners: What's your side of the story?

If you own or manage Chestnut Hill Bed & Breakfast Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.