Chestnut Hill Bed & Breakfast

3.0 star property

5.0/5 Exceptional

Guests rated this property 5.0/5 for cleanliness.

Popular amenities

  • Free WiFi
  • Breakfast included
  • Parking available
  • Room service
Caroline Street 236, 236, Orange, VA, 22960

Explore the area

  • Popular LocationLake Anna29 min drive
  • AirportCharlottesville, VA (CHO-Charlottesville-Albemarle)40 min drive
  • Popular LocationUniversity of Virginia42 min drive
  • Popular LocationSwift Run Gap Entrance Shenandoah50 min drive

Choose dates to view prices

About this area


Chestnut Hill Bed & Breakfast is located in Orange. James Madison Museum and The Arts Center in Orange are cultural highlights, and some of the area's landmarks include Montpelier and James Madison's Montpelier. Guests appreciate the hotel's central location.

What's nearby

  • James Madison Museum - 6 min walk
  • St. Thomas Episcopal Church - 7 min walk
  • Lake Anna - 29 min drive
  • University of Virginia - 42 min drive
  • Swift Run Gap Entrance Shenandoah - 50 min drive

Getting around

  • Culpeper Station - 29 min drive
  • Charlottesville-Albemarle Airport (CHO) - 40 min drive


  • Real Food — 7 min walk
  • Wise Guys Burgers and More — 11 min walk
  • Pizza Hut — 11 min walk
  • The Light Well — 11 min walk
  • Happy Garden — 11 min walk

About this property

Chestnut Hill Bed & Breakfast

3-star hotel in Orange with free breakfast
Self parking, concierge services, and wedding services are available at this smoke-free hotel. Free continental breakfast, free wired Internet in public areas, and a free manager's reception are also provided. All 6 individually decorated rooms feature WiFi and pillowtop beds. Other amenities that guests will find include room service and flat-screen TVs.
Chestnut Hill Bed & Breakfast offers 6 accommodations with designer toiletries. Each accommodation is individually furnished and decorated. Beds feature pillowtop mattresses. Flat-screen televisions are featured in guestrooms. This Orange hotel provides wireless Internet access for a surcharge.

Property amenities


  • Available in all rooms: WiFi (surcharge)
  • Available in some public areas: Free wired internet

Parking and transportation

  • Self parking on site (surcharge)

Food and drink

  • Free continental breakfast
  • Free reception
  • Room service available

Guest services

  • Concierge services
  • Front desk (limited hours)
  • Wedding services


  • Smoke-free property

Room amenities


  • Pillow-top mattress


  • Designer toiletries


  • Flat-screen TV


  • Individually decorated
  • Individually furnished

See similar properties


Special check-in instructions

To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation
If you are planning to arrive after 8 PM please contact the property in advance using the information on the booking confirmation
Guests must contact the property for check-in information


Pets allowed for an extra charge

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

Important information

Optional extras

The following fees and deposits are charged by the property at time of service, check-in, or check-out.

  • A pet fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards

Property is also known as

Chestnut Hill Bed & Breakfast
Chestnut Hill Bed & Breakfast Orange
Chestnut Hill Orange
Chestnut Hill Bed Breakfast
Chestnut Hill Orange
Chestnut Hill Bed Breakfast
Chestnut Hill Bed & Breakfast Hotel
Chestnut Hill Bed & Breakfast Orange
Chestnut Hill Bed & Breakfast Hotel Orange

Frequently asked questions

Overall score and ratings



Rating 5 - Excellent. 13 out of 13 reviews
5 - Excellent 100%
Rating 4 - Good. 0 out of 13 reviews
4 - Good 0%
Rating 3 - Okay. 0 out of 13 reviews
3 - Okay 0%
Rating 2 - Poor. 0 out of 13 reviews
2 - Poor 0%
Rating 1 - Terrible. 0 out of 13 reviews
1 - Terrible 0%




Staff & service


Property conditions & facilities

5/5 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wonderful getaway!
Arrived late afternoon for a get away with a friend. Was welcomed with wine and Old Bay steamed shrimp, cheese platter. Relaxed on comfy seating on porch, saw family of 6 deer. Everything in the b&b was beautifully furnished and the hosts were very accommodating. Another family was there and we chatted with them a lot! The beds had wonderful sheets, lots of extras in the bathroom. And amazing breakfasts both days, a fruit course, then main course: Grand Marnier French Toast w/ lemon asparagus and bacon, an eggs benedict like meal with avocado and melon, plenty of juice, tea and coffee. And the setting for breakfast was amazing. They also provided vouchers for 2 wineries nearby that they recommended, gave us printed directions, and both places were terrific! The downtown area was nearby along with restaurants which we never even needed with all the great food. The 2nd night was mini crabcakes on pasta or chicken wings! So relaxing, wonderful experience!
Stayed 2 nights in Aug 2017

5/5 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great Experience
Our experience with this B&B was the best. Attention to detail and facility was first rate.

5/5 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wonderful inn in a great location!
We spent our anniversary weekend with Kathleen and Troy at their wonderful B&B - Chestnut Hill. They are exceptional hosts - making sure everyone feels welcome and comfortable. The evening happy hours and yummy breakfasts were great. We recommend this lovely inn for that special celebration or just a get away weekend to enjoy the Charlottesville, VA area - history, wineries and more.

5/5 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

5/5 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfect romantic getaway in a gorgeous surrounding, just 40 minutes from Hiking trails in Shenandoah or Charlotsville. Kathleen and Troy are wonderful hosts. The house is amazing, the hosts paid great attention to every detail and it is somptuous. The breakfast is fantastic. You will want to bring the bed with you or at least the bedsheets. That was the main topic of conversation at the breakfast table. The best sleep I had in years. I definitely will go back.