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Chestnut Hill Bed & Breakfast

236 Caroline Street , Orange, VA 22960 USA (Show map)
461 Reviews
$179 - $295
per night

Check Dates Diamond Collection

Professionally Inspected & Certified


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.

Rooms & Rates


Standard Description

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

Nightly Rate: N/A

Check Dates



Write A Review

  • Guest room4.9
  • Services5.0
  • Value4.9
  • Cleanliness5.0
  • Dining5.0

Score Breakdown based on
461 Reviews

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My Eldest Son's Wedding Event

5 on April 21, 2014

What a truly delightful weekend! Everything about this B&B is elegant in a very, very quaint, relaxing and simplified way. The rooms, the decor, the landscaping, the meals,... All of it combined to make unforgettable memories I shall cherish forever! I'm so delighted my son and daughter-in-law chose this beautiful and elegant B&B setting for their wedding celebration! I can't wait to tell everyone I know about my weekend at Chestnut Hill and I am already planning to return.

Perfect retreat

5 on April 09, 2014

This was my first time going alone to a B&B for a mini "retreat." The Chestnut Hill B&B proved to be the perfect place. Kathleen and Troy are gracious hosts who make you feel comfortable and at home. Troy's delicious lobster bisque was an outstanding way to begin my stay. The breakfast was delightful, and the room was lovely and very spacious. Kathleen even delivered wine, the bisque and the next morning, the breakfast to my room so I could enjoy some much needed quiet alone time. I can't say enough about my wonderful stay here. I hope to be back soon!

Wonderful Stay

4.6 on March 16, 2014

We had a lovely stay at Chestnut Hill this past week! We stayed in Ask Anna and were thrilled with the spacious, luxurious, and comfy room! The only thing that could have made the room better is if the heat had been turned up just a tad, but with this crazy weather it's hard to know what temperature to set things at. The food was excellent, the staff helpful and pleasant, and Kathleen and Troy were great at meeting are requests and activities! Thank you to everyone at Chestnut Hill for making our stay perfect!


5 on January 30, 2014

Once again, the stay at Chesnut Hill was fabulous. The staff is wonderful. They are courteous, professional and extremely attentive to the wants of their guests. The breakfast and happy hours are fantastic. The morning breakfast with the roasted pineapple with pistachios and raspberry chocolate sauce was superb. The rooms are comfortable and allow you to escape. It's the ultimate Bed and Breakfast. And dinner and everything else. The grounds are beautifully manicured. We will definitely come back for years and years.

Best in Virginia

5 on January 25, 2014

This was our sixth stay with Troy and Kathleen and it has become like a second home.The hospitality is unmatched and the inn is beautiful. If you want to get away and relax, Chestnut Hill is the place to go.

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Location Type

Countryside, Mountains, Small town, Wine country


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

Directions to property:

Take the US-250 exit, EXIT 124, toward SHADWELL/CHARLOTTESVILLE and turn RIGHT onto RICHMOND RD/US-250 E. Travel approximately 2 miles. Stay STRAIGHT to go onto LOUISA RD/VA-22 and continue to travel approximately 5.5 miles. Stay STRAIGHT to go onto GORDONSVILLE RD/VA-231. Continue to follow VA-231 N for approximately 9.6 miles. Enter next roundabout and take 2nd exit onto US-15 N and travel 8.4 miles to first traffic light. DO NOT proceed through traffic light intersection. The entrance to Chestnut Hill B&B is on the left JUST before this traffic light intersection

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

Historic Inn, Bed and Breakfast

On-site amenities

Board games, CD player, Ceiling fans, Computer, Copier, DVD Player, In-room internet, 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 , 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


  • Check In:: 4:00 - 6:00 p.m
  • Check Out:: 11:00 a.m.
  • Open All Year Round: Yes
  • Smoking Allowed: Limited
  • Drinking Allowed: Yes
  • Suitable For Children: Supervised & well behaved children of all ages are welcome.
  • Guest Pets Allowed: Limited You are welcome to enjoy our two resident lap dogs.

Terms and Conditions

  • Minimum Stay: Two night minimum for weekends, holidays and special events
  • 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


Check Dates




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

Special meal options

Low fat , Restrictive , Vegetarian

Details Diamond Collection

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

Property highlights

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