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.
All 7 Orange B&Bs / inns

Chestnut Hill Bed & Breakfast Inn

3.5 of 5 Bed and Breakfast   |   236 Caroline Street, Orange, VA 22960
Hotel website
Hotel amenities
Save Saved
You added Chestnut Hill Bed & Breakfast Inn to your Saves list
Chestnut Hill Bed & Breakfast Inn
Best prices for your stay
Enter dates for best prices
Check In Check Out
Show Prices
You must enter dates to see the best prices.
Ranked #1 of 7 Orange B&B and Inns
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 2 weeks ago
scottwyden Manalapan, New Jersey
  • Overview
  • Reviews (210)
  • Photos (62)
  • Amenities
  • Q&A
  • Room tips (45)
  • Location
  • More
Write a Review

210 people have reviewed this hotel

Traveler rating
See reviews for
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 (45)
Date | Rating
  • English first
  • Any
English first
Manalapan, New Jersey
1 review
5 of 5 stars Reviewed 2 weeks ago

When my wife and I arrived we were greeted as if we were walking into our own home. That sums up the entire experience. It felt like our home away from home. The room was beautiful and the atmosphere was so relaxing and friendly. Chestnut Hill is close enough to some amazing sightseeing opportunities and wineries. During our stay we... More

Was this review helpful? Yes
Middletown, Virginia
Top Contributor
81 reviews 81 reviews
6 hotel reviews
28 helpful votes 28 helpful votes
5 of 5 stars Reviewed 2 weeks ago

Kathleen is definitely in the right business. She is welcoming, friendly, and informative. The inn is beautiful and every detail was thought through for the rooms. Breakfast was delicious, but the best part was meeting the other guests!

Was this review helpful? Yes
Washington DC, District of Columbia
2 reviews
5 of 5 stars Reviewed 4 weeks ago

My wife and I would absolutely stay here again. This is a beautiful inn in a lovely area. The staff go the extra mile, as evident in every aspect of the impeccable service, food, and amenities. Also, the staff have intimate knowledge of the region, and answer any questions you may have to ensure you get the most out of... More

Was this review helpful? Yes
Kommetjie, South Africa
1 review
5 of 5 stars Reviewed June 26, 2014

Everything about our experience at Chestnut Hill Bed & Breakfast went above and beyond what we expected of our overnight getaway. We knew we were staying at a nice B & B arranged by my in-laws for our anniversary, but we had no idea how wonderful it would be. Kathleen and Troy are such lovely people, so hospitable and warm,... More

Was this review helpful? Yes
Washington Township, New Jersey
2 reviews
5 of 5 stars Reviewed June 19, 2014

Our stay at Chestnut Hill was our first Bed & Breakfast experience. We were overwhelmed from the first moment we stepped into this lovely home. Kathleen welcomed us as if we were beloved friends. Our room was beautiful and comfortable. Breakfast each day was beyond our expectations. We shared enjoyable conversations and sharing with the other guests during Happy Hour... More

Was this review helpful? Yes
Clinton, Maryland
1 review
5 of 5 stars Reviewed June 18, 2014

This was my first experience with a bed and breakfast and I have to say Troy, Kathleen, and Lea exceeded my expectations. From the service throughout our stay and the coordination and planning of my wedding. Everyone was so welcoming to not only us but our families. Also, the grounds and the rooms are absolutely beautiful. Let me not forget... More

Was this review helpful? Yes
4 reviews 4 reviews
5 of 5 stars Reviewed June 14, 2014

My husband and I just returned home from an amazing anniversary getaway at Chestnut Hill Bed and Breakfast. Kathleen was wonderful! She was so accommodating and really went the extra mile to make us feel welcome and special on our visit. We stayed in the Emily Macon Bridal Suite which is a beautiful large room on the top floor. All... More

Was this review helpful? Yes
Atlanta, Georgia
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 13, 2014

First of all the house and property is amazing! My sister's wedding was here.. Just this past weekend. We cannot stop talking about this bed and breakfast! Everyone had a great time. Kathleen and Troy.. The whole family was so welcoming and friendly. Great service, great food. Hard workers!

Was this review helpful? Yes 1
Odenton, Maryland
1 review
5 of 5 stars Reviewed June 3, 2014

Chestnut Hill hosted my sister's wedding over the weekend, and we had a magnificent time. Troy and Kathleen were very attentive from the time we arrived. They run a professional operation which provided an outstanding breakfast each morning... it was phenomenal. I would definitely stay there again, and will be referring my friends and family. The rooms were well kept... More

Was this review helpful? Yes
Locust Grove, Virginia
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 1, 2014

The Chestnut Hill B&B was a luxurious retreat. Tory and Kathleen are so friendly and helpful. They welcomed us into their home and made us feel like their special guests. The home is beautiful and the land scape is gorgeous. We had a wonderful relaxing and romantic anniversary!

Was this review helpful? Yes 1
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.
Manage your listing

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
Price Range (Based on Average Rates): $$
Hotel Class:3.5 star — Chestnut Hill Bed & Breakfast Inn 3.5*
Reservation Options:
TripAdvisor is proud to partner with Priceline, Tingo, Expedia, Hotels.com, Travelocity and Agoda 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.

62 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (41)
Hotel & grounds (7)
Dining (3)
Room/suite (7)
Bathroom (4)
Other (20)

Management photos: Courtesy of the property manager

All management photos (22)
Room/suite (4)
Hotel & grounds (4)
Dining (1)
Other (13)


Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Room Service Suites
Hotel Class
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 
Number of rooms

Questions & Answers

Enter your question for this accommodation's staff to answer. Other travelers may answer as well.
    Posting guidelines

    See which rooms travelers prefer