Chester Inn


Chester Inn – 1900 to Present Day

In the late 1800s and 1900s, Chester went through numerous remodels and renovations, bringing it closer and closer to the beautiful home it is today!

Chester Inn Bed and Breakfast in Scottsville

In 1880, the first indoor plumbing came to Chester as the north addition was built on the first floor. We do not know the location of the original outhouse, but are sure that this was a welcome change. In 1900, a caretaker’s cottage was built next door and remains to this day. In 1910, closets were added. Prior to this time, trunks and armoires would have been used to store clothing. In 1915, a second floor was built on top of the 1880 addition. During the 1920s, a small basement was dug, presumably for food storage.

Chester Inn in Scottsville

In the 1930s, four porches were added on the north, south, east, and west sides of the house, adding fluted Doric columns and Greek Revival balustrades to the west façade and Tuscan columns to the north and south ends of the house. These additions brought an elegance that had not existed before. A total of eight woodburning chimneys were also installed over the years, all of which are still working today.

Water was originally supplied by a well underneath the shady, screened east porch. This well has been capped for some time now, and Chester uses water for city sources and a well in the front yard. There are likely many archaeological treasures and clues to be found in the original well. Hot water was brought to the house by great-grandparents of current Scottsville residents. Many clues as to the evolution of Chester are found during renovations, when you can see names, and dates signed onto the beams and infrastructure of the house.

In 1954, Harold and Ruby Parr purchased the house, and in turn, sold it to Gordon Anderson and Dick Schaffer in 1985. After an extensive kitchen renovation and refurbishing of the house, it was opened for the first time as a bed & breakfast. In 1995, Anderson and Schaffer sold the property and the business to us, and we’ve been here ever since.

As the current caretakers of this amazing piece of history, we have lovingly maintained its grace and elegance, while adding our own touches, including an expansion of the east back porch, where we enjoy birdwatching and morning coffee, and the addition of an ornamental fish pond and patio off of the north porch. The house was fully renovated in 1995 to ensure that each of our rooms were modernized and had private baths, and we reopened for business in 1996. Over the last 26 years, we have witnessed so many occasions in this home—from graduations, reunions and weddings to memorials, company dinners, and romantic retreats.

historic holly tree at Chester Inn in ScottsvilleThe grounds still house most of the original plant specimens from the 1800s. The oak tree in the front yard—one of the largest in the state—predates the home itself. Chester is home to the second largest holly tree on record in the state. Our beautiful white pine held the state record for largest tree until it came down several years ago. In its honor, we had the tree milled into lumber and replanked the kitchen floor with it, so it remains with us—just in a different way.

Despite its colorful history, we have never seen any ghosts at Chester, so we invite you to come and visit without trepidation. Simply enjoy the many details and beauty that make this one of the grandest homes and properties in central Virginia.

Everyone who has visited Chester has left their imprint on its history, and it is our hope that Chester has left an imprint on them as well. We hope that you will join us in continuing to make history here.Chester Bed and Breakfast near Charlottesville




Chester Through the Mid-1800s

With the Chester established by Joseph C. Wright, the home and grounds that we know and love today began to take shape throughout the 1840s.

Mr. Wright began to plant many specimens of trees and shrubs throughout the property over the next several decades, most of which remain on the arboretum grounds today. As was fitting of his British heritage, he introduced stands of English boxwood, which grow very slowly (less than an inch each year).

These boughs are in great demand during the holiday season and are still trimmed each year by distributors who then send Chester boxwood off to florists throughout the country.

In 1851, Mr. Wright added a stable and sold Chester to John H. Coleman, but continued to live there as a caretaker. Coleman sold the property in 1853 to George Walton Dillard for $2,375. The price of sale continued to fluctuate and the property changed hands several times, actually once moving from the seller to the buyer and back again. In total, the Dillard family lived on the property for over 100 years.

The Dillards used the house as a country retreat from their lives in Richmond. During their time at Chester, many additions and changes were made to the home and grounds. During the early years of the Civil War, Chester was known as one of the “party houses” in a town surging with prosperity. There were picnics, dinner parties, quilting bees, teas, dances, and even ice skating on the pond that still remains on the property.

In 1865, Scottsville saw the full brunt of the Civil War. Sheridan and Union troops raided the town while Major Hill was occupying Chester, recovering from an amputated arm. Colonel George Custer and Sheridan came to visit and decided not to arrest who they thought was a “dying man.” They left Chester alone, Major Hill recovered, and the house remained unscathed.

170 Years of History in the Making

It is often said that owners of historic homes are simply caretakers of its past and present, keeping it alive for those who come in the future. At the historic Chester Inn, we are so honored and privileged to have been the caretakers of this majestic house and property for 26 years!  We are delighted to share that this year marks the 170th anniversary of Chester’s creation. Over the coming weeks, we will be sharing photos and interesting facts about our historic Virginia home here and on Facebook. To provide those of you with a keen interest information about how this home has evolved since the first board was laid in 1847.

Chester Inn Historic Virginia Home

The first records we have of Chester shows the arboretum grounds that the historic home sits on were owned by John Scott, whom you might notice shares the same name as the town we live in and was, fittingly, the founder of Scottsville, Virginia. James K. Polk was the current President of the United States, and Scottsville was prospering on the busy horseshoe bend of the James River, which was the main conduit of commerce and travel through central Virginia. In 1830, he sold the property for $325 (about $8,250 in today’s dollar) and it was sold again in 1831 for an unspecified amount. At this time, there was no building on the property yet.

After an 1841 private sale, it was sold at public auction after payments had not been kept up. Joseph C. Wright arrived in town during this period from Chester, England and purchased the property. A landscape architect by trade, he built the original structure right after Thomas Jefferson’s Monticello was finished, using many of the same construction methods.

Historic Chester Original StairsThe original house had two stories and was three bays wide. Built in the popular Greek Revival style, the foundation was propped on large boulders that were already on the land. Hand-hewn oak beams from trees on the property still support the original structure. The original stairs, banisters and molded handrails built by Joseph Wright remain to this day, standing as an example of the quality of these construction methods.

The home was finished in weatherboard of heart pine, which is known for producing a tremendous amount of resin. Much of this resin remains today, keeping paint from adhering to certain parts of the exterior, despite our best attempts to paint!

The pitched roof was laid in an intricate fish scale design made with slate from neighboring Buckingham County in a raised manner to promote air circulation within the home and to keep the slate dry. Two single chimneys adorned the house and provided heat for both cooking and comfort during the winters.

Stay posted for the next few weeks as we continue to discover the history behind Chester Bed and Breakfast in Scottsville, Va!

Two respites…one heart

Spring at Chester Bed and Breakfast in CharlottesvilleEveryone has a respite: a short period of rest or relief from something difficult or unpleasant. For some, it’s a good book. For others, it’s a walk or a run. Over the last 25 years, we at Chester feel blessed to have been a respite for many visitors–lots of whom have become good friends over the years. We’ve had visitors from all around the world–from Texas, Florida, and Georgia to the UK, Mexico, California, and even Anguilla.

Today, our hearts are heavy as we think about all of those affected by the recent natural disasters–be it fire, earthquake, or hurricane–it seems that everyone is hurting in some way. Our thoughts are particularly with our beloved Anguilla, where we head for OUR respite each winter. As innkeepers, we need a place where we can go to recharge for the coming year. The beautiful island and its amazing people have been devastated by Hurricane Irma, and we are helpless to do anything at the moment.

So we continue with what we do here at Chester: serve as a respite for those who need it. We are lucky enough to have the beauty and peace of two respites in our lives. Please give us a call or email us if you need to get away from the chaos of life for a few days…our doors are open, we have rooms available, and a walk on our arboretum grounds is always good for the soul.

Sending love and good thoughts to all.

The James River in Scottsville

Scottsville James River

Looking for a fun day activity near Chester Bed and Breakfast? Take a day and visit the James River in Scottsville! On its way from Botetourt County to the Chesapeake Bay, the James River takes a sharp horseshoe bend in the center of Scottsville’s downtown area and treats visitors and residents of Scottsville to a variety of river activities. Enjoy canoeing, kayaking, tubing, rafting, fishing and more, all within easy access from Downtown Scottsville. From downtown, you can access the James River from a boat launch just off of main street or, a few miles west of town, there is a small public park and the Hatton Ferry.

The Hatton Ferry is another hidden treasure of Scottsville, as it is the last poled ferry in the United States. Establish in 1870, the Hatton Ferry still takes visitors across the James on weekends in April and October and offers a unique step back in time to see how the ferry got folks across the river before the Scottsville bridge was built. Now completely run on donations, it’s definitely worth a little drive to see the ferry and visit the newly installed exhibit about the ferry and its history.

Even if you are a visitor, getting on the water is easy with the help of Scottsville’s many river outfitters, who offer canoeing, kayaking, rafting, and tubing trips and equipment, as well as guides and shuttle services. They make a day on the river easy to plan and stress-free, so all you have to worry about is whether or not you’ll get a good tan.

The James River is also known for some of the best small mouth bass fishing in the nation, so bring your own gear or rent equipment. Many river outfitters offer high-quality fishing equipment for rent for full or half days, and will let you in on what’s biting, the best bait, and where the sweet spots are.

For a special treat, come by Scottsville’s leg of the James in June for a glimpse at the James River Batteau Festival! This year, the eight-day festival will stop in Scottsville on June 21st, giving you the chance to check out the authentic replicas of the sleek, shallow-draft merchant boats that used to travel the James for trade. Stay for the evening festival and be treated to the cultural heritage of this legendary river basin in music, song, dance and storytelling.

If you are in Scottsville for a day, a weekend, or a week, be sure to fit the James into your schedule somewhere. Whether it’s just for an hour or a whole weekend, one thing is for certain, nothing is better than spending a hot summer day relaxing in the James.

Spring has Sprung at Chester

Looking for a romantic Virginia bed and breakfast getaway to relieve your cabin fever? Visit Chester Bed and Breakfast in Scottsville and discover why it is the perfect ‘Spring Break’ for any single, couple or family looking for a weekend getaway or extended stay near Charlottesville.

Spring at Chester Bed and Breakfast in CharlottesvilleDiscover carefully curated landscaping that showcases spring’s natural beauty. Enjoy the outdoors from our historic bed and breakfast’s porch with your morning coffee, take a walk around the property, have a picnic on the lawn, or read a book by the koi pond. Chester abounds in beautiful landscaping to enjoy, while our location outside of Charlottesville offers a secluded and quite feeling, while being right beside downtown Scottsville, and only 20 minutes from all Charlottesville has to offer.

Discover spring events and activities in the surrounding area. Scottsville is the ideal location for any spring activity, including hiking, biking, fishing, and canoeing and kayaking! Visit James River Reeling and Rafting just down the road for tubing trips and kayak rentals. Additionally, check out our Plan Your Stay page for links and resourced to all sorts of local events and activities.

Discover spring specials and planned activities. Chester Bed and Breakfast regularly offers specials and can help you plan your perfect getaway. View our seasonal Specials to see what is happening at Chester this spring, or call us to discuss specially planned dining or having wine delivered to your room for an evening beside your own cozy fireplace. We can also help you plan wine tours to the surrounding wine country, suggest local hiking trips, and much more!

A Virginian spring has so much to offer, and Chester Bed and Breakfast helps you take advantage of it all conveniently and easily. From wineries to hiking to kayaking on the James, don’t forget to stay at Chester when planning your next Charlottesville spring getaway!

Valentines Weekend at Chester

Looking for a place to get away from it all with your special someone? Look no further. Chester is an intimate and private getaway where you can focus on each other. Our warm and welcoming rooms have beautiful four-poster beds, cozy chairs, luxurious linens, oriental rugs, and private baths. Gourmet breakfasts are served at your own fireside table each morning, and our arboretum grounds are the perfect place for a morning walk with a hot cup of coffee.

Charlottesville b&b valentines dayVenture just down the road to explore our local brewery, have a casual Italian bite, or walk the levy by the great horseshoe bend of the James River. Plan a visit to the many local vineyards that surround the inn, or head into Charlottesville for five-star dining and wonderful shopping. Zip up to Wintergreen for some seasonal skiing or snowboarding. Whether you stay in bed all weekend or explore all the things that our area has to offer, you’ll definitely feel like you’ve gotten away from it all!

Autumn Vacations

We all know about the typical Summer Vacation; going to the beach or the lake with family, roadtrips, camping, theme parks, everyone has their own tradition. But after the summer is over, don’t think that vacationing has to come to an end! Here at Chester Bed and Breakfast, autumn and winter are some of the best times for a full vacation or mini getaway, and we can show you why!

Weather: The weather through September, October, and early November can still be beautiful. The crisp air is perfect for hiking, sightseeing, reading on the porch, walking downtown and shopping, playing yard games, and more! Even in late November and December, when it gets cold, what is better than sitting in front of a crackling fire and sipping wine? Chester bed and breakfast in Charlottesville fireplace

Location: Since we are located just outside of Charlottesville, Chester Bed and Breakfast makes an ideal weekend getaway in the fall or winter. We are close enough to be close to town and attractions, but far enough from Charlottesville to feel like you have gotten away from it all.

We have some of Charlottesville’s best wineries within a 15-minute drive and most of the Monticello Wine trail just a little further.

Shenandoah National Park is just on the other side of Charlottesville and during the fall is one of Virginia’s most scenic drives! The cool and crisp air of fall and winter makes overlooks and views more clear and spectacular than during the summer.

Timing: With students back to school, autumn is an ideal time to visit landmarks, take tours, do some sightseeing, or take a stroll downtown. There will be less crowds, less traffic, and some attractions even offer “off-season” discounts or reduced prices for people visiting during the fall and winter months.

Virginia also offers some of the best in fall foliage, which makes autumn timed vacations extra special because of extra special scenery. Visiting historic homes, picnics, hiking, and even just driving becomes more pleasant as the fall colors come in.

These are just some of the many reasons to take an autumn or winter vacation and Chester Bed and Breakfast is the ideal place to stay! Nestled in the quiet, quaint part of Albemarle County, Chester Bed and Breakfast is perfect for a relaxing autumn or winter getaway. Be sure to call and ask about our Fall and Holiday Specials, and book your room now for the upcoming season.

Chester Bed and Breakfast in Charlottesville, Va in Winter





Mustangs in Scottsville

Legacy Mustang Preservation in Scottsville VA

Wild horses in Scottsville? Most people aren’t aware of the American Mustang sanctuary in Scottsville, VA, which is a short country drive from Charlottesville.

With a 250-acre sanctuary, Legacy Mustang Preservation is on a mission to provide a nurturing environment for the American Mustang. Their efforts promote the understanding, appreciation, and adoption of the unique American breed and promotes specialized training that focuses on the needs of the wild horse.

Located just over the James river in the scenic Albemarle/Fluvanna countryside, and less than a 10-minute drive from Chester Bed & Breakfast, the preservation can be visited and frequently hosts promotional events at the sanctuary.

Coming up soon in September is their Hoofing it with the Herd 5k Walk & Run. Which will take place on the beautiful 250-acre preservation and is a family friendly event, after the race there will be food, music, and a “meet the mustangs tour”!

They also host a yearly Mustangs Helping Mustangs car show benefit at the sanctuary that promotes the love of both Wheeled and Hooved Mustangs!

Support of the preservation can also be found in donations and volunteering,  and promotional events are frequently held at Scottsville businesses, such as a recent Community Tap Night hosted by the local James River Brewery.

Albemarle county is known for its love of horses and the sanctuary embodies this love of riding and caring for our equine friends. During your next stay at Chester Bed & Breakfast don’t miss a visit to this hidden gem of Albemarle, or many of the other local businesses in beautiful Scottsville!

Summer in Charlottesville and Scottsville

Bed and Breakfast Charlottesville

With music events and concerts, festivals and fairs, and entertainment and nightly happenings, summer is one of the best times to enjoy Charlottesville, the Blue Ridge and all of beautiful Albemarle county! Whether it is for an overnight trip, a weekend getaway, or a week-long vacation, Charlottesville offers some of the best entertainment for Virginia summers.

Beat the heat by taking a shady hike in Shenandoah National Park, or visiting a local swimming hole, like our favorite Crabtree Falls. Get to know the local history by visiting Thomas Jefferson’s Monticello, James Monroe’s Ash-Lawn Highland, or the Albemarle Historical Society, which has over 1500 artifacts of Charlottesville history. Bring the kids along and enjoy family-friendly museums, activities and festivals all summer long! Like the Virginia Discovery MuseumAlbemarle County Fair, Carter Mountain Orchard’s Peach Festival, and Monticello’s Heritage Harvest Festival, just to name a few. Enjoy arts and culture at the Fralin Museum of Art and the 24 hour IX Art Park.

That’s just a handful of the parks, museums, and festivals that Charlottesville offers. There is so much to do in Albemarle, the hard part will be fitting it all into your summer!


Don’t Forget Scottsville!

But along with bustling Charlottesville, don’t forget the perfect place to take a weekend getaway is right here in scenic Scottsville! Our own Chester Inn is less than a mile from beautiful downtown Scottsville and the James River. For history buffs, look no further than the Scottsville Museum and take a walk through the Historic District to enjoy almost one hundred old buildings, homes, and shops from the 18th and 19th century. On Saturday mornings visit the Scottsville Farmers Market, which features local food, music, and crafts; and once a month enjoy the Scottsville Second Saturday Art Walk, which turns downtown Scottsville into an art gallery and also features live music, activities for kids, and local food and wine tastings.

So whether you are planning a family vacation, wine tour, weekend getaway, honeymoon, or just a relaxing overnight stay, our Chester Inn is the perfect home base for any summer break to beautiful Albemarle county!