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Chestnut Hill Bed & Breakfast

236 Caroline Street , Orange, VA 22960 USA (Show map)
4.9
469 Reviews
$179 - $295
per night

Check Dates

BedandBreakfast.com Diamond Collection

Professionally Inspected & Certified

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.

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

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

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

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

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

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

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Reviews

Overall
4.9

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

Score Breakdown based on
469 Reviews

Write A Review

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?


Beautiful B&B

4.0 on October 20, 2014

My husband and I stayed at Chestnut Hill for one night on October 13, 2014. The home is beautiful with much attention to detail. Beautifully decorated and very well kept. Kathleen and Troy were very gracious hosts! We stayed in "Ask Anna" and it was a stunning room, especially the whirlpool tub. Breakfast in the morning was outstanding, and the snacks in the evening were a very nice touch. While we were there, a small wedding ceremony took place in the back yard. Very nice venue for a small wedding. The rate is expensive, but it's a lovely place to stay for a special occasion.


Best ever!

5 on October 04, 2014

Owners "very" friendly...Made us feel at home!! By far the best B&B we have ever visited!! The breakfast was fantastic!! Want to visit again!


Dream come True

5 on August 13, 2014

My husband and I got married at the Inn on August 2, 2014 and rented the entire B&B for the weekend. We knew when we rented that the establishment was beautiful, but actually having the Chestnut experience created the most romantic wedding weekend ever! Our family who occupied the rooms were stunned by the beauty, amenities, the service, the food, and just the small personal touches that you would find in a 5 star diamond hotel. When I returned to work, people who weren't invited were coming up asking for pictures because those that went bragged that it was the most beautiful wedding they had ever seen. Troy and Kathleen were awesome and went out of their way to make our stay and our wedding exactly how we wanted and were so accommodating of our crazy wedding schedules. Troy was awesome at throwing compliments that made me feel like a was the best bride ever and Kathleen kept me so calm! My husband and I are planning another getaway there soon and it had only been a week! Don't think, just do it! It is worth every penny!


Five Stars in Every Category!

5 on August 11, 2014

Chestnut Hill is both beautiful and friendly! We hope to return many times--if we can get reservations--it's almost always booked up. We would highly recommend it to anyone who wants comfort in an elegant home with plenty of relaxing spaces: the back porch, the huge downstairs den, the formal living room, the second floor lounge. Chestnut Hill also deserves its reputation for outstanding multi-course breakfasts. It's a superb B&B and a great getaway.


This Place is the Best

5 on July 28, 2014

My now husband and I stumbled upon this delightful bed and breakfast on accident when searching for a place to elope. First off, the building itself, as well as the surrounding property, is stunning inside and out. It has been completely renovated and was the perfect backdrop for our ceremony. The innkeepers, Troy and Kathleen are the most friendly people that you will ever encounter. They treated us like VIPs the entire time. As far as the ceremony goes, all we had to do was get a license and show up. They took care of absolutely everything else. Breakfast and an evening appetizer is included in the stay. Even though Kathleen assured me that neither she nor Troy went to culinary school, you would think differently. They made the most delicious food from the best ingredients. We never needed to eat lunch because breakfast was so amazing and filling. We cannot wait to come back to Chestnut Hill for our first anniversary. I would recommend this bed and breakfast to anyone looking for a fun and fancy yet relaxing place to stay or site for your wedding. It's really the best. ~Megan and Jason


Superb

5 on July 08, 2014

My wife and I would absolutely stay here again. This is a beautiful inn in a lovely area. The staff go the extra mile, as evident in every aspect of the impeccable service, food, and amenities. Also, the staff have intimate knowledge of the region, and answer any questions you may have to ensure you get the most out of the local attractions. This was a very relaxing, enjoyable stay.


Our Anniversary Trip

5 on May 11, 2014

Chestnut Hill Bed and Breakfast is the best place to visit for a little relaxation! Troy and Kathleen made our stay perfect in every way. The atmosphere and warm greeting was outstanding. Our room was comfortable and so charming.


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!


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Location

Location Type

Countryside, Mountains, Small town, Wine country

Airport

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, 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 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: 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 S, y, s, t, e, m, ., C, o, l, l, e, c, t, i, o, n, s, ., G, e, n, e, r, i, c, ., L, i, s, t, `, 1, [, S, y, s, t, e, m, ., S, t, r, i, n, g, ]
  • 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.

Innkeepers

Name(s)

Kathleen & Troy Ayers

Languages spoken

English

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


Details

BedandBreakfast.com Diamond Collection

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

Property highlights


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