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

Romantic getaway without kids;)

5 on April 09, 2016

Perfection in every way! This was my first experience in a bed and breakfast, and the hosts at this establishment have converted me to B&B's for all my traveling. The ambience was relaxed yet refined. Breakfast was fabulous, and the town of Orange is simply magical!


Another wonderful Valentines Day!

5 on March 01, 2016

My wife and I spent Valentines Day 2015 at Chestnut Hill, and loved it so much, we went back for 2016. The staff is extremely friendly and helpful and the food is delicious! The place is very tastefully decorated and extremely clean. We already plan to be back for 2017. Thank you for a romantic weekend!


Well worth the second visit!

5 on February 21, 2016

This was our second time staying at Chestnut Hill. Troy, Kathleen and the entire staff are extremely friendly and outgoing. The food is great, the rooms are very clean and everyone goes out of their way to make your stay wonderful. We plan to be back next Valentines Day!


Baby moon

4.2 on February 21, 2016

My husband and I wanted to take a few days and relax before we become parents. Chestnut Hill Bed and Breakfast was the perfect place for that! It was so beautiful and relaxing. Kathleen and Troy were amazing! They made sure we we're comfortable the whole time. They both took the time to get to know us. We did not feel like passerbyers. We felt like part of the family. A really classy family. They provided us with many ideas for things to do on our little relaxing trip. They know how to run this elegant establishment. It was really hard for us to leave because we were so comfortable there. Thank you Kathleen and Troy for making this really remember able for us! Ron and Jill.


Best weekend wedding

5 on February 03, 2016

My husband and I had our wedding here. Chestnut hill took care of EVERYTHING! Flowers, food, music, ceremony, cake, champagne. All of the things you expect in a full size wedding we had in our weekend getaway with 25 of our closest friends. The rooms are like a dream getaway. Kathleen and Troy really know how to take care of their guests.


Outstanding B&B in Orange, VA

5 on January 15, 2016

We enjoyed a wonderful night in December at Chestnut Hill B&B to celebrate our anniversary. The room was beautiful, the breakfast delicious and plentiful, and the hosts were wonderful and friendly. . Stay Mon-Wed and enjoy free wine, beer and soft drinks. We have stayed in several B&Bs in Virginia and elsewhere and this is the best of the bunch!! You will not be disappointed.


best bed in virginia hands down

5 on December 14, 2015

The inn keepers are wonderful they give you a feelings of being at home that I've never expirenced before. They have a beautiful house and great recommendations. It's defiantly worth every cent spent at this bed and breakfast.


Wedding event

4.4 on November 20, 2015

I was here for sister wedding.Everything is very nice along with wedding ceremony! I enjoyed my stay so much my boyfriend and I booked another night. Rooms are clean, beautiful, and beds are comfortable. Owners very friendly and welcoming. I plan your visit again soon!


A Lovely Stay

3.6 on November 06, 2015

This is a beautifully restored Inn built in the 1860 with comfort at its best and a great location as well. Our stay was delightful. Troy & Kathleen Ayers are just fantastic hosts making you feel welcome. The rooms are lovely and there is an open wine and beverage bar downstairs. Each day a creative hors d'oeuvre is prepared and served. The breakfast is fantastic and beautifully served as well. There are fresh baked cookies each day to enjoy. Stay here when you get the chance and you will be so happy you did.


Fabulous Stay at Chestnut Hill!

5 on October 31, 2015

Just had the pleasure of staying at one of the best B&Bs in the Country; Chestnut Hill. Kathleen and Troy were great hosts and made us feel right at home. We purchased the Wine tour package and spent the day visiting 4 great wineries and being chauffeured around in a stretch limo. Troy and Kathleen gave us the history of the property and lots great advice on which wineries to visit and where to eat dinner in the area. The rooms are nicely decorated and very comfortable and our room had 2 gas fireplaces and a large 2 person jacuzzi tub. We had a great nights sleep and awoke to the wonderful smell of breakfast and fresh coffee. We joined 4 other couples in the dining room for a delicious and well prepared gourmet breakfast that truly was a treat and left us all stuffed. The staff is very attentive and always available to ensure you enjoy your stay. When it was time to go, Troy and Kathleen met us on the back porch and we chatted for awhile and felt as if we were old friends, We really hated to get in the car and leave. Chestnut Hill is quite a treasure and you will not find better hosts than Troy and Kathleen. Highly recommended and we can't wait to visit 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 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

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 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

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 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

Nightly Rate: $229 - $245

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

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

  • 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

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

Nightly Rate: $179 - $195

Location

Location Type

Countryside, Mountains, Small town, Wine country

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

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

Check Dates Visit Website

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: Prior approval required
  • 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.

Innkeepers

Name(s)

Kathleen & Troy Ayers

Languages spoken

English

Resident Pets

Check Dates Visit Website

Meals

Breakfast

Full

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

Special meal options

Low fat , Restrictive , Vegetarian