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There is no better way to experience the magic of our bed and breakfast inn than to visit when you are in the Charlottesville area, but we have a taste for you here to help whet your appetite for the many delights of our historic inn:
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Chester provides an intimate and private setting for luxurious comfort and relaxation. Each of our rooms is a peaceful retreat from everyday life. Even a short stay will reenergize and rejuvenate you.
Welcoming glasses of wine and full gourmet breakfasts are included with each room.


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Guest Rooms
Each guest room is elegantly designed for your comfort. All of our accommodations have four-poster queen beds, oriental rugs, luxury linens, nightly turndown service, L'Occitane amenities, woodburning fireplaces, central air, and private baths. The inn is climate-controlled year-round for your comfort, and offers wireless internet access in most guestrooms and common areas.
Room 1 - American Holly
Nestled off of the library in the North wing of the house, this room is spacious and inviting, with two comfortable wing chairs by the wood burning fireplace for reading and visiting. Fall asleep to the gentle sound of the garden fountain, and step onto the patio from your own private entrance for an early morning walk or a cup of coffee by the pond. All of our rooms have private baths.
Room 2 - Tulip Poplar
With a four-poster bed facing the wood burning fireplace, this room is perfect for a romantic getaway. Enjoy views of the garden pond, and relax with a glass of wine or cup of coffee in the Southern rockers on the adjacent North Porch. Two wing chairs surround the fireplace for conversation, reading, or relaxing. A spacious private bathroom completes the room.
Room 3 - Magnolia
A sumptuous chaise lounge next to the wood burning fireplace and a romantic four-poster wrought iron bed make this a cozy and inviting space to unwind. The private bath has a large glass-enclosed shower. Overlooking the back lawn, it's the perfect room for stress-free relaxation.
Room 4 - White Oak
This spacious, light-filled second-floor room overlooks the 300-year-old oak tree on the front lawn and much of the Chester grounds through its four original large windows. A favorite with bridal and anniversary couples, this secluded room sits in the South wing of the house and features a sitting area, writing desk, and spacious bathroom.
Room 5 - Franklinia
Overlooking the front lawn, this second-floor room has a beautiful and private view from the four-poster bed. Two wing chairs surround the wood burning fireplace, and the spacious bathroom overlooks the 300-year-old majestic oak tree through a privacy shade.
The Cottage Suite
Our Cottage Suite provides a private and peaceful environment for relaxation. The warm and inviting sitting room is a cozy place to relax in front of the gaslight fire, enjoy a movie on a flat-screen television, or play a game of cards. The kitchenette is equipped with a refrigerator and microwave. The writing desk in the large bedroom overlooks the back lawn and woods and the four-poster bed is the perfect place to end your day. In the morning, relax in the rocking chairs on your private porch with a cup of coffee or tea before joining us in the dining room for breakfast.
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A two-night minimum stay is generally required on all weekends in April through November and certain holiday weekends. If you need a single night stay during this time, please call to inquire about availability.
Wireless internet access (Wi-Fi) is available in most guestrooms and common areas. Please ask for a Wi-Fi enabled room when booking.
Check-in is at 4:00 pm and check-out is 11:00 am.
Visa and Mastercard are accepted. As a small business, we welcome checks and cash, and offer a complimentary bottle of wine for all guests paying in either of those ways.
Cancellation Policy: Full refund with ten days notice. For cancellations with less than ten days notice, deposits will be refunded if the accommodations can be rebooked. Event deposits are non-refundable.
If you have questions about our services, a need for more information, or comments about our website please call us or Email us. We want to hear from you!
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