Chestnut Hill Bed & Breakfast

236 Caroline Street , Orange, VA 22960 USA (Show map) Diamond Collection

Professionally Inspected & Certified Diamond Collection


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.



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  • Guest room4.9
  • Service5.0
  • Value4.9
  • Cleanliness5.0
  • Onsite Dining5.0

One of the best!

5 on October 21, 2015

We absolutely loved Chestnut Hill. We stayed in the Alexander Daley suite and it was perfect! Kathleen and Troy are excellent hosts and the breakfasts are fabulous. We had a wonderful time and if we return to the area, we'll be sure to return to the inn. Stay there - you'll be glad you did!

Luxury for a great price

5 on October 17, 2015

Chestnut Hill is like a mini all-inclusive resort experience. Wonderful cookies and a great hours d'oeuvre on check in, easy access to great local wines, beer, sodas and coffee or tea, clean and excellently decorated rooms with the softest bed I've ever slept in, and an outstanding breakfast in a refined setting. Stay here; you'll be glad you did.

Wonderful anniversary getaway

5 on September 25, 2015

My husband and I had our honeymoon at Chestnut Hill, so is was great to come back and receive the same top notch service that we previously had before. Kathleen called ahead to see if we needed reservations for dinner and recommend several local places to eat, and they also recommended several local wineries to go to once we arrived. The room we had previously stay in was already booked, but when we arrived, we found out that the person had cancelled and Kathleen had already moved us over to that room. We love how the owners make an effort to remember folks. It really makes a difference, and we will certainly be back!

Exemplary service/hospitality

4.4 on September 22, 2015

Kathryn and Troy do a terrific job in accommodating their guests!

4th Visit & Still a Winner!

5 on March 25, 2015

We've stayed with Troy & Kathleen 4 times now and each visit has been a pleasure! Nice rooms, warm hospitality and excellent food make Chestnut Hill a B&B we will keep coming back to and recommend to our friends.

Expectations exceeded!

5 on March 06, 2015

We stay at BnB's frequently and the Chestnut Hill Inn was by far the best. Every aspect was AAA+, from the warmth of the proprietors to the food to the atmosphere to the accommodations. B. Gleason

Wake to Chestnut Hill

5 on January 22, 2015

Chestnut Hill far exceeded my expectations. Kathleen, Troy, Leona et al were beyond fantastic. Breakfast was "Robin Leech" (of "Lifestyles of the Rich and Famous") worthy. The B&B is centrally located 30 minutes from Monticello and 10 minutes from Montpelier. Vineyards abound short driving distances away. Local restaurants are hidden gems and Troy and Kathleen were knowledgeable about them all. One day you wake up and realize value in accommodations, services and, in this case, location, are more important then the "deal of the day". If you value these things then you owe it to yourself to "wake up at Chestnut Hill". We will be back!

The ultimate getaway...

5 on December 10, 2014

We've always thought you have to go far away to experience sublime luxury. We never thought there is such luxury, hospitality and so much to experience, a mere hour outside of the Washington, DC area.

Happy Birthday Getaway

5 on November 17, 2014

Outstanding evening all the way around. Hospitality upon arrival was warm and inviting. The innkeeper went above and beyond to meet our requests. The other guests were personable. The value was exceptional.

Columbus Day Getaway

4.8 on October 20, 2014

My wife and I decided to get away for our anniversary a little early this year in the hope of seeing some fall color. We chose Chestnut Hill after looking at several other B&Bs. So the weather didn't cooperate as it rained the entire time, but the stay at Chestnut Hill was great. Kathleen and Troy were very pleasant and accommodating helping us make the most of our celebration. And did I mention the breakfasts were delicious?

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Rooms & Rates

Alexander Daley's Master Suite

ALEXANDER DALEY S MASTER SUITE One of Chestnut Hill s favorites Majestically appointed with only the finest furnishings and decor Overlooking the front garden and formal fountain with a view of the quaint town of Orange Queen size four poster pillow top bed dressed in triple sheeted superior quality cotton sheets and deluxe down pillows and comforter Lush cozy spa robes and oversized luxurious bath sheets are a perfect accompaniment to your relaxing spa bath Two gas fireplaces Walk in closet 32 HD flat screen television Romantic chandelier lit private bath with gas fire

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Emily Macon's Bridal Suite

EMILY MACON S BRIDAL SUITE Surround yourself with pure luxury comfort and uncompromised service at every corner on your wedding day with only the finest of furnishings and delicate bridal decor Overlooking the front formal gardens and cascading fountain with a view of the quaint town of Orange Queen size exquisitely carved four poster pillow top bed dressed in superior quality triple sheeted cotton sheets and deluxe down pillows and comforter Lush cozy spa robes and oversized luxurious bath sheets Dressing table with lighted make up mirror Double closet Separate living area

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Four Quarters

FOUR QUARTERS You ll just have to ask Serenely lit room on the second floor overlooking the back gardens fountain and scenic hillside of Chestnut Hill This guest room is your destination for memorable Virginia weekend getaways The custom duvet draperies seating area and bath decor are adorned and furnished in a luxurious style Perfect for a romantic get away King size pillow top bed dressed in superior quality cotton sheets and deluxe down pillows and comforters Lush cozy spa robes 32 mounted HD flat screen television Double closet Private bath with custom porcelain tile

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

Ask Anna

ASK ANN When in doubt This room is situated in our lower level multi media entertainment area and is adorned with Imported Mahogany Hardwood floors luxurious rich gold and burgundy decor and elegantly hand painted furnishings Just step outside your room and enjoy the bar area or watch a movie on our 60 plasma television The private bath has a Jacuzzi tub and separate glass enclosed shower The chandelier lit bathroom has exquisite custom tile with copper accents and oversized porcelain pedestal sink and Jacuzzi tub Queen size pillow top bed dressed in Superior quality cotton

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Pink Serendipity

PINK SERENDIPITY The faculty of making fortunate discoveries by accident Romantically secluded on the third floor of Chestnut Hill it reveals the original brick work of the chimney that was raised in the 1870 s when the mansard roof was added This softly lit room is graced with hardwood floors and ceilings and overlooks the back gardens and scenic hillside Queen size pillow top bed dressed in triple sheeted superior quality cotton sheets and deluxe down pillows and comforter Lush cozy spa robes 32 HD mounted flat screen television Double closet Private bath with custom porcelain

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Kate's Coincidence

KATE S COINCIDENCE Situated just off our lower level multi media entertainment area and offers a commercial chair lift situated just outside the quarters that is conveniently accessible to the driveway and designated parking Just step outside your room and enjoy the bar area or watch a movie on our 60 plasma television Beautifully decorated and furnished this room is also equipped with safety bars and other amenities that make it equally enjoyable for our guests with special needs Please ask us for more details about our dedication to accommodating guests with medical requirements

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

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Location Type

Countryside, Mountains, Small town, Wine country


Charlottesville, VA (CHO-Charlottesville-Albemarle) 25 miles

Directions to property:

From the North: (DC, Baltimore, Northern Virginia) Travel South on I-95 into Virginia to VA-3 west via exit number 130B towards Culpeper. Proceed approximately 13 miles and turn left on onto VA-20/CONSTITUTION HWY. Continue to follow VA-20/CONSTITUTION HWY 22 miles to the second traffic light. This traffic light is the intersection of US-15/CAROLINE ST/VA-20. From this intersection you can see Chestnut Hill Bed and Breakfast Inn. At this intersection, turn left onto US-15/CAROLINE ST/VA-20 and then make an IMMEDIATE first right into our driveway.

Area Attractions

Antique Shopping, Art Galleries, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Museum, National/State parks, Nature area, Performing Theater, Picnic area, Religious Services, River, Rodeo, Ruins, Ski area, Vineyard, Winery

Inn Details

Establishment type

Bed and Breakfast, Historic Inn

On-site amenities

Board games, CD player, Ceiling fans, Computer, Copier, DVD Player, Desk, Fax Machine, Fireplace, Hot tub/whirlpool tub, Internet Service, Library, TV Video games, Telephone, VCR, Videos, Washer/dryer, Wedding Facilities, Wet bar, Wi-Fi, Wired internet , Koi Pond with Waterfall, Outdoor Water Fountain Feature, Social Area with 62 inch Entertainment Center, Bridal Suite, Business Center, Library

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, Hairdryer, Radio, Satellite/Cable TV, TV, Turndown Service

Check Dates Visit Website


  • Check In:: 4:00 - 6:00 p.m
  • Check Out:: 11:00 a.m.
  • Open All Year Round: Yes
  • Smoking Allowed: Outside only
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Yes Supervised & well behaved children of all ages are welcome.
  • Childcare Provided: No
  • Guest Pets Allowed: Prior approval required You are welcome to enjoy our two resident lap dogs.
  • Disabled Access Yes

Terms and Conditions

  • Minimum Stay: Two night minimum for weekends, holidays and special events
  • Accepted payments Other, AMEX, VISA, Discover, Mastercard, Personal checks, Cash
  • Deposit Amount Required: Reservations are made with a 50% Deposit. Balance is due upon arrival. All payments made by check must be received at least seven days prior to check in.
  • Cancellations: Refunds, minus a $25.00 cancellation fee, will be provided if cancellation request is received at least 10 days prior to arrival date. Deposits are not refundable unless the room is rebooked.



Kathleen & Troy Ayers

Languages spoken


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  • Time Served: 9:00 a.m.
  • Serving Location: Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian