Chestnut Hill Bed & Breakfast

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

BedandBreakfast.com Diamond Collection

Professionally Inspected & Certified

BedandBreakfast.com Diamond Collection

About

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.

Reviews

Overall
4.9

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  • Guest room4.9
  • Service5.0
  • Value4.9
  • Cleanliness5.0
  • Onsite Dining4.9

Weekend Stay at Chestnut Hill Bed & Breakfast

5 on March 07, 2018

Over the Valentine's Day holiday, we enjoyed a special 3-day-2-night get-away at Chestnut Hill Bed & Breakfast. We had a wonderful experience: outstanding accommodations, great conversation with guest and owners, delicious breakfast and fabulous appetizers and wine were included with our package, along with complimentary winery tours. If you are planning a romantic weekend w/ your special sweetheart, we highly recommend you check out this venue. If you are planning a intimate or large wedding or event, Chestnut Hill is a must do!


Great relaxing stay....

4.2 on January 07, 2018

My wife and I stayed with Kathleen over New Year's Eve. The B&B had a lot of character. The room was very nice and spotless. Breakfast was original and luxurious and different every morning. We thoroughly enjoyed the family style atmosphere and great conversations with other guests. Before our stay we got perfect assistance to arrange New Year's Eve activities in the area. We also enjoyed the winery arrangement, In short a perfect and relaxing stay. Exactly what we were looking for and more...


Exactly what a Bed and Breakfast should be

5 on May 30, 2017

Kathleen and Troy were the ultimate hosts. I wish we could have stayed longer. This was a lovely place to stay on the way to Monticello. And the picnic that they packed for us was fantastic! Both the inn and the hosts are a Virginia treasure.


Awesome stay

3.6 on April 03, 2017

The stay with really good, the room was very neat. The hosts treated us very well.


Teresa

5 on March 21, 2017

I visited Chestnut Hill for my daughter's wedding venue this past weekend. The home and grounds are beautiful and well kept. The staff were amazing and ready to help us with our every need. Plus, they helped us with another one of our daughter's wedding in the past. They make you feel just like you are part of their family. Thanks for all that you have done for us!!!!!


Outstanding Hospitality!

5 on March 13, 2017

Chestnut Hill B&B was the perfect get-away to celebrate my husband's 60th birthday! Kathleen & Troy are wonderful people and innkeepers, ensuring every aspect of our stay was as special as a 60th birthday should be! We highly recommend Chestnut Hill B&B!


Amazing as always

5 on March 06, 2017

We stayed in the bridal suite, which is beautiful. The atmosphere of Chestnut Hill is relaxing, Troy and Kathleen are gracious hosts, and the breakfasts (and afternoon appetizers) were wonderful. We try to get to this Bed and Breakfast at least once a year - no other Bed and Breakfast compares to this one!


A Must Stay

5 on February 17, 2017

Kathleen & Troy treat guests like family!!! The house and grounds are unique and beautiful. We were married there 6 years ago and keep coming back year after year because its so peaceful and such a stress relieving environment. Troy is an excellent Chef and the breakfast is out of this world. Kathleen is a wonderful host and very funny too! They will exceed your expectations!!!


Amazing B&B!!!

5 on February 03, 2017

I had an amazing stay at Chestnut Hill B&B! We stayed in the Alexander Daley's Master Suite and as you can see from the pictures it was beautifully decorated and really felt like home. When we arrived Kathy gave us a tour and then took us right up to our room. She even let us see the Bridal Suite just in case we wanted to switch for the night. We got the Romance package and everything went exactly according to plan! The massages were great, she set up dinner for us at one of the restaurants she recommended (which was absolutely amazing), they even had special treats from the chef for us to try, and then brought us breakfast to the room in the morning! My boyfriend was celebrating his birthday and each part of the package was supposed to feel like a surprise and with Kathy's help I was definitely able to make his birthday special.


Perfect gem

5 on January 19, 2017

What a perfect gem! The renovation produced a perfect blend of retaining period architecture while introducing modern conveniences. The hosts are lovely and accommodating while remaining unobtrusive. Breakfast was excellent and were tips of where to get dinner. The location is ideal for a visit to Barboursville and Horton wineries. Plan to return to enjoy again.


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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 décor. 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 fireplace, two-person Jacuzzi tub, his & her porcelain dual saucer sinks mounted on a handsome acacia wood dressing table imported from India, exhilarating multi-spray shower, and custom designed tile throughout.

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

Nightly Rate: $259 - $285

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 décor. 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 with 42” HD flat-screen television in living quarters and finely detailed wet bar with complimentarily stocked refrigerator; Enjoy the extravagance of the romantic private bath with lavish claw-foot tub and separate glass enclosed shower adorned with superior quality personal amenities and luxurious bath sheets. Magnificent custom designed tile throughout.

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

Nightly Rate: $269 - $295

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 décor 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 •Seating area

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

Nightly Rate: $229 - $245

Ask Anna

ASK ANNA - 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 décor 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 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; 32” HD mounted flat screen television; Luxuriously appointed private bath with custom tile and two-person Jacuzzi tub; Oversized pedestal sink.

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

Nightly Rate: $229 - $245

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 tile; Oversized pedestal sink; Seating area.

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

Nightly Rate: $209 - $225

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 and our commitment to the American’s with Disabilities Act. Queen size, pillow-top bed dressed in superior quality cotton sheets and deluxe down pillows and comforter; Lush, cozy spa robes; 27” HD mounted flat screen television; Luxuriously appointed private bath with custom roll- in shower and five foot turn around for wheelchair accessibility.

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

Nightly Rate: $179 - $195

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Location

Location Type

Countryside, Mountains, Small town, Wine country

Airport

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, Sports venue, Vineyard, Winery

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Inn Details

Establishment type

Historic Inn

On-site amenities

Board games, CD player, Ceiling fans, Computer, Copier, DVD Player, Desk, Fax Machine, Fireplace, Hot tub/whirlpool tub, 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

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Policies

  • 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: Limited
  • Childcare Provided: No
  • Guest Pets Allowed: No
  • 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 $35.00 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 re-booked.
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Innkeepers

Name(s)

Kathleen & Troy Ayers

Languages spoken

English

Resident Pets

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Meals

Breakfast

Full

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

Special meal options

Low fat , Restrictive , Vegetarian


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