Visiting the area and not sure where to stay? Let us help you with that. The following come highly recommended and are convenient to tour wineries, breweries, cideries, or distilleries.

Planning your weekend has never been easier! Book a room at the wonderful Hyatt Place, reserve dinner within walking distance at Travinia’s Italian Kitchen and Wine Bar, and let Central Virginia Wine Tours customize a perfect tour to your liking of Charlottesville’s beautiful wineries, breweries, cideries, and distilleries!

Click the following regions to view specific places to stay.



Orange/Madison/Keswick/Barboursville/Louisa/Lake Anna/Ruckersville






Charlottesville, Virginia

The Fairfield Inn & Suites Charlottesville hotel near the University of Virginia is located along I-29 between The Shops at Stonefield and Charlottesville Fashion Square Mall. Enjoy easy access to area businesses, Foxfield Races, Scott Stadium, John Paul Jones Arena, wedding venues, and the Monticello Wine Trail. Savor a free hot breakfast before walking to Food Lion to grab a picnic lunch for tours of Monticello and area wineries. Explore Charlottesville as the Historic Downtown Mall, Appalachian Trail, Shenandoah National Park, and panoramic views along Skyline Drive are minutes from our Charlottesville, VA hotel. Here to do business with Dominion Power, JAG, NGIC, GE, Mikro Systems, Sentara Martha Jefferson Hospital or the UVA Medical Center? Stay connected using our free WiFi and business center. Relax in our spacious rooms and suites and take advantage of room and hotel amenities such as a fridge, microwave, fitness center, and an outdoor pool. Stay at our Marriott hotel in Charlottesville, VA.
Click here for Hotel Website
The welcoming Homewood Suites by Hilton® Charlottesville, VA hotel is moments away from the Seminole Square Shopping Center, the Shops at Stonefield and the Fashion Square Mall, which offers shops, eateries and the area’s only IMAX theater. Take a short drive to historic downtown Charlottesville, home to boutiques, restaurants, the Discovery Museum and ice skating, and explore the Downtown Mall for a charming ‘old town’ atmosphere. Enjoy easy access to the University of Virginia, Skyline Drive and the Blue Ridge Parkway. Our extended-stay Charlottesville hotel is also minutes from historical sites, including James Monroe’s estate, Ash Lawn-Highland and the adjacent Monticello, Thomas Jefferson’s home.
Admire rolling hills and swans swimming in the pond at Hilton Garden Inn Charlottesville in Charlottesville, VA. Located on the property formerly owned by Thomas Jefferson’s father, our hotel is accessible from I-64 and off US 250 bypass. Drive three miles to historic downtown Charlottesville, VA, 12 miles to the Charlottesville-Albemarle Airport, or four miles to the University of Virginia. Call for our complimentary shuttle, serving all Charlottesville destinations.Select from 124 Charlottesville, VA hotel rooms and suites. Wake up to freshly made coffee in your room. Check emails with complimentary WiFi and print remotely to our complimentary business center.Our Charlottesville hotel offers 1,700 sq. ft. for meetings and social events. Plan a banquet for 100 people or invite 12 potential clients to our boardroom with modern AV equipment. Nearby businesses include the Federal Executive Institute, Martha Jefferson Hospital, and the US Army Judge Advocate General School.Unwind in the Pavilion Lounge with a drink or in the fitness center with a workout. Soothe tired muscles in our indoor whirlpool. We offer dinner at the Garden Grille & Bar®, evening room service and quick meals from the 24-hour Pavilion Pantry®
Guesthouses Reservation Services provides unique accommodations in Charlottesville and Albemarle County, Virginia. Select from bed and breakfast style guest rooms in private homes or private suites with your own private entrance to a room, a suite or a full apartment. Perhaps you prefer a cottage or log cabin or a whole house.

Whether your trip is a romantic getaway, a family adventure, a business venture, or a visit with your UVa student, Guesthouses will assist you in finding a one-of-a-kind accommodation. Nightly, weekly, and monthly stays available. Bringing fido? Let us help you find pet-friendly accommodations. 

Welcome to the Holiday Inn Express & Suites Charlottesville-Ruckersville, located in the center of Virginia wine country.  Our ideally located hotel is the perfect place to stay, whether you are staying on business in the Charlottesville VA area, or visiting for leisure.No matter the reason for your stay, don’t miss out on the opportunity to visit a local vineyard for a one-of-a-kind wine tasting experience.  There are also a variety of local breweries and great things to do in the city of Charlottesville.Central Virginia Wine Tours is proud to provide winery/brewery tours as well as transportation for weddings and bachelor/bachelorette outings.
Hyatt Place Charlottesville  is centrally located in the Shops at Stonefield with many dining, entertainment, and shopping options just steps away. Featuring 137 guest rooms with A.M. Gallery Buffet Breakfast, internet, and parking included in rate.A LEED certified hotel featuring five car charging stations complimentary to guests. Property features include an indoor pool, fitness center, and complimentary use of guest laundry.
Welcome to our Bed and Breakfast located two blocks off Charlottesville’s Historic Pedestrian Mall, one mile from the University of Virginia and four miles from Thomas Jefferson’s home, Monticello. This inn offers old world elegance and pleasant lodging in Charlottesville’s lively downtown district. All of our accommodations include breakfast each morning and a room with its own private bath. Free parking and high speed internet are available to all of our guests.
The Inn at 400 West High brings the eclectic flair of a continental European bed and breakfast to beautiful downtown Charlottesville, Virginia, with luxury accommodations, freshly prepared breakfast, and a full cookie jar. The Inn is an oasis of relaxation and beauty in which to unwind after a day at the vineyards, wineries, and breweries, hiking in the Blue Ridge Mountains, or the whirlwind celebrations of a wedding weekend.
Set in 100 acres of grounds, this upscale hotel in a white-painted mansion, is 6 miles from the Jefferson Theater and a 7-mile drive from historic Michie Tavern.  Individually decorated rooms and suites feature elegant decor and free WiFi. Some add antique furnishings, claw-foot tubs and/or patios, while suites include pull-out sofas, living areas, and/or garden or mountain views. There’s also a carriage house with a loft. Free continental breakfast and afternoon tea are served on the veranda, and there’s an elegant restaurant with a terrace serving American cuisine. Other amenities include an outdoor pool, a hot tub and a croquet lawn.
This country-modern B&B is 8.7 miles from Charlottesville and 20.2 miles from the North Entrance of Blue Ridge Parkway.  The sophisticated rooms feature handmade furniture, en suite bathrooms, free WiFi and high-end stereo systems. Most rooms have whirlpool tubs and remote-controlled fireplaces; some also add pull-out loveseats and bay windows. Amenities include a 3-course breakfast made with local ingredients and a stocked pantry with a refrigerator, a microwave and a coffeemaker. Cookies and fruit are available in the afternoon. There’s a TV and media library in the sunroom, as well as a fishpond and a secluded hot tub on the grounds.
Woodville Bed and Breakfast is an ideal hotel alternative, offering comfortable accommodations, delicious breakfasts, and warm hospitality in the rural historic area of Southern Albemarle County, VA. Built in 1892, this elegant country manor home has been lovingly restored with modern amenities added to provide the perfect location for a luxurious getaway. Spend your days exploring the areas many attractions, lounge by the pool, take a stroll through the vineyard and grounds, or sit back and simply enjoy the view. If you are searching for a romantic or simply relaxing Virginia Getaway look no further than Woodville Bed & Breakfast.
If you are looking for a romantic getaway in a serene location, away from the hustle and bustle, The Inn at Sugar Hollow Farm is your place!

We are at your service to ensure you feel right at home here in the country. Enjoy fresh air, forests, mountain trails, and wooded streams, great food and friendly hospitality in the best of Virginia Wine Country.

Here at the inn we have a small working farm that includes two ponies, eight dwarf size goats and a couple of dozen hens and roosters. Keeping an eye on them are our five dogs. Two great pyrenees, a basset hound, and two beagle basset mixes. Come stay with us and meet them all and enjoy fresh eggs at breakfast!

Orange, Virginia and surrounding areas

Orange, Virginia 22960, Phone: 540-672 7001   Nestled in Virginia’s horse and wine country in the foothills of the Blue Ridge Mountains lays an exceptional, new property called The Inn at Willow Grove. Now open following a massive renovation, The Inn at Willow Grove welcomes romantic weekenders, countryside tourists or colonial history buffs to come experience any of the 14 luxurious rooms and suites. Guests will enjoy unparalleled, five-star services infused with world-class designs while surrounded by historic 18th century architecture.
Welcome to Round Hill Inn, located in Historic Orange Virginia.  Our Hotel is nestled on top of a hill of several acres with beautiful endless views of the Blue Ridge Mountains, some of which exceed 45 miles, rolling hillside and working farms. We are located within minutes of Historical attractions such as Montpelier, Monticello, Wilderness and Chancellorsville battlefields. Also take some time to explore some of the 20 plus vineyards located just minutes from us.
Welcome to Mayhurst Estate. 

One of Virginia’s most beautiful Italianate and Victorian style homes.
Mayhurst is over 9,500 square feet, 5 levels, has 14 fireplaces, and over 36 acres of trails, grounds, and beautiful spaces to relax and unwind after a great day of exploring.
Mayhurst was built in 1859 by President James Madison’s great nephew and has been home to much history over the years.  Mayhurst has 8 beautiful guest rooms with each having its own style and story.  Mayhurst offers a gourmet breakfast each morning as well as a host of other amenities to our guests.  Come and enjoy one of Virginia’s most beautiful gems.
2333 N. James Madison Hwy, Locust Dale, VA 22948, Phone:540-672-4912 The essence of Virginia … Romantic, historic 1700s country inn and restaurant offers elegant accommodations, acclaimed fine dining, extensive Virginia wine list, gracious setting and warm hospitality. 10 stunning guest accommodations await your pleasure at the Inn at Meander Plantation
“The historic Holladay House, right on Main St. in Orange, Virginia, is the perfect base from which to explore Central Virginia, with its historic homes and battlefields, many wineries and microbreweries, and amazing scenery punctuated by beautiful farms. The house had hosted residents and guests from Virginia’s finest families, including the Madisons, Pages, Taliafferos, and even JEB Stuart. Elopements and events welcome!”
Quiet. Natural. Simple. This is our motto and our atmosphere when you join us at the Uphill House B&B! Our modern bed and breakfast features five beautiful guest rooms and is situated on a secluded, wooded 11 acre property. While at the Uphill House you will enjoy amenities such as complimentary WIFI, in suite baths, plush robes and hairdryers, two convenient breakfast times, TV in the main living room and two guest rooms, homemade pastries and afternoon snacks, complimentary beverages, and a spacious back deck complete with swing and fire pit. Comfort is our number one priority and it is our pleasure to help you relax, so come on Uphill and let us take care of you! Scott and Samantha Darling, Innkeepers
Located in beautiful Somerset, VA, Spotswood Lodge is an 11-acre farm house & cottage rental. Operated by The Market at Grelen, it is open to couples who are getting married at Grelen or any of the other amazing venues in the Orange County area.  With eight bedrooms and seven full baths, it’s a wonderful option for wedding parties and/or families of the bride and groom.   Of course, weddings are not the only reason to consider renting The Lodge.  If you’re looking for a place for a family reunion, company retreat or just searching for the perfect country getaway, look no further. More details:
8 bedrooms, 7 full baths
Sleeps 16-20
Three day minimum
Three day rental:  $2500 for both houses or $2000 for main house
Six day rental: $3500 for both houses or $3000 for main house
Cleaning Fee (including linens):  $500 for both houses or $300 for main house
Innkeepers – The Webb Family, Doris, Alan, and Amy, 122 Seville Rd., Rt. 621 West, Madison, VA 22727, Phone: 540-948-3695The Ebenezer House is a Family Friendly country chalet. A home away from home. Seven miles south of Madison, just 500 feet off of US 29. Close to all historical sites, restaurants, and local vineyards and the beautiful Blue Ridge Mountains. Full Country breakfast with friendly conversation will begin your day.
Wolf Trap Farm offers Vacation Rental and limited Bed & Breakfast accommodations on a 584 acre horse and cattle farm, with mountain views, miles of forest trails, rolling pastures, abundant creeks and brooks, nine ponds, and easy access to all the attractions of Charlottesville and the Central Virginia area.
Well Hung Vineyard Restaurant Cottage “Pillow Talk”
Conveniently located in the heart of downtown Gordonsville, this newly renovated home offers 2 bedrooms w/ queen beds, full bathroom and ½ bath, full kitchen, office space, living room, and washer & dryer. High speed internet, keyless entry, private driveway & street parking available.  Enjoy shopping at local boutiques, wineries & restaurants all within walking distance PLUS a 20% discount at Well Hung Vineyard Restaurant!
You’ll be centrally located in Orange with a stay at Comfort Inn & Suites Orange – Montpelier, minutes from James Madison Museum and St. Thomas Episcopal Church. This hotel is within the vicinity of The Arts Center in Orange and James Madison’s Montpelier.
Overlooking Southwest Mountains, Chanticleer Cottage sits on 55 acres of farmland with restful country views but within minutes of Charlottesville, Gordonsville, Barboursville, Orange, Woodberry, Virginia’s historic sites–Monticello, Montpelier, and Univ of Virginia–and many scenic wineries. Even with the pastoral setting, the Cottage is close to family as well as elegant, refined dining. The Cottage is a wonderful option for extended family visits, weddings, graduations, and winery touring.
Located just outside the town of Orange, Virginia, The founders of Grelen Nursery & The Market at Grelen have renovated this lovely 1891 home to add to their event & lodging options for their Market at Grelen guests and area visitors.  In good shape structurally, this gem, set on an expansive 13.6 acre parcel, just needed a little redesign, TLC and  refreshed landscaping.  Named for it’s large boxwood circling the house, Boxwood Villa is surprisingly private so close to town and a wonderful addition to The Grelen properties.  
Welcome to Magnolia Place, a newly renovated historic home in Central Virginia. Located in Gordonsville, 30 mins north of Charlottesville, this is the perfect central hub for all your exploration including Shenandoah National Park, Monticello, Montpelier, UVA, and the surrounding wineries/breweries. Built in 1905, the home features many original details and is equipped with modern amenities. Spacious and serene, this is the perfect place to spend time with family and friends for a long weekend.
Magnolia Farm is a working Cattle and Horse Farm located at the end of a private .75 mile long driveway. Walk down to the bridge to listen to the creek, explore the trails through the 108 acre property, have an outdoor fire in the garden, or relax in the gazebo swing. Only 5 minutes to downtown Gordonsville and 25 minutes to Charlottesville. This home was built in 1910 and completely renovated in 2017.
Book Directly from Owners Browse our  many Lake Anna Vacation Rental Homes By Owner. 45+ Waterfront, Pet Friendly, Handicap Accessible, Water Access, and Water View Homes. We even Homes for small Weddings! Check out our Last Minute Deals for
additional saving.

Step back in time and experience the romance, relaxation, and history of Prospect Hill Plantation Inn & Restaurant… the oldest continually-operating frame-house plantation in Virginia, and a founding member of Select Registry™.  Once an authentic 18th century wheat plantation, Prospect Hill was long-ago transformed into a premier Charlottesville-area bed & breakfast.  Between the Manor House and the nine original dependencies (circa 1699 – 1890), we offer thirteen distinctive guest rooms and cottages. By keeping each cottage’s original function as intact as possible, our accommodations vary from elegant to rustic. All, however, are packed with character, brimming with history, and tell a purely Southern story of folklore and tradition. With private baths, working fireplaces, creaky floors, expansive views, and incomparable romantic charm… each room tells the history of another era.  A recipient of AAA’s “Four-Diamond Award of Excellence for Dining and Lodging”, Prospect Hill has long been one of central Virginia’s best-kept “secrets” for exquisite fine dining.  Nestled on 40 pastoral acres, the grounds at Prospect Hill are magnificently beautiful.  Whether reclining by the pool, reflecting by the garden gazebo, strolling the expansive grounds, or hand-feeding horses, alpacas, and chickens… the magic of Prospect Hill will make leaving difficult… and returning a near necessity!

UVA, wineries, weddings, craft breweries nearby! Need flexible space and timing for gathering friends and family? All 7 night stays are priced at 5 nights’ rate, with 2 free.

Wildwood is perfectly situated to enjoy the area year-round: wineries, James Madison’s Montpelier, Monticello, hikes, music, sports, graduations, weddings, and most importantly, reunions of friends and family.

Our home is ideal for families/large groups! Tucked away in the heart of Virginia’s wine country, Guildford Farm welcomes you with cozy rooms, beautiful views, and peaceful relaxation. We are located just 15-30 minutes from local wineries, 20 miles from the University of Virginia, and 10 miles from the Shenandoah National Park.

The space

This is still used as our private residence, so please treat it kindly. We ask that you treat our home with as much respect as you would treat your own. If an accident does occur, we ask that you let us know as soon as possible so we can get it taken care of.

Built in the 1790’s, Guildford Farm was the original home of the Early family, the namesake of Earlysville, VA. In 2003, the nearly 8,000 square foot country home was completely restored. The home contains 7 bedrooms, 5 bathrooms, 10 foot ceilings, and a stunning 13 original fireplaces (not suitable for use). During the restoration, the original architecture of the home was meticulously preserved. The inside of the home offers exquisite woodwork, hand-carved mantels and wide heart pine floors. The home is located in the middle of a 100-acre picturesque estate overlooking a 2-acre pond to the East and the majestic Blue Ridge Mountains to the West.

**Please note we are a working farm. Although rare, we do occasionally have lawn maintenance (cutting hay/maintaining the fields) on the property. Additionally, there is an event center on the property that is not included with this listing. This should in no way disrupt your stay as we never book events when our Airbnb is rented it is roughly 150 yards away from the house!*

The Hampton Inn – Suites Culpeper is situated perfectly in the heart of Culpeper near Lake Pelham Culpeper Country Club and just a short drive to Shenandoah National Park for all your outdoor recreational activities. There is nearby shopping at Southgate Shopping Center and Culpeper Town Square and plenty of local restaurants including Luigi*s Italian Restaurant Piedmont Steakhouse and Shawn*s Smokehouse BBQ. Our Culpeper hotel rooms are fresh and modern spaces with a microwave mini-fridge 42-inch HDTV coffeemaker and a work desk with ergonomic chair. Feel rested after a great night*s sleep on the clean and fresh Hampton bed and stay connected with free WiFi and plenty of device-charging spots. Suites offer more space with a sleeper sofa great for family stays. tart each day with a free hot breakfast of freshly baked waffles eggs bacon cereal fruit and other favorites. We also offer free coffee and tea service in the lobby. Work out in the 24-hour fitness center or go for a swim in the indoor heated pool. We also have a business center and meeting space.
Inspired by Thoreau’s Walden, Walden Hall is a luxury Bed and Breakfast and event space nestled in the foothills of the Blue Ridge Mountains. This beautiful home sits on 10 acres of rolling farmland in the tranquil countryside of Reva, Virginia; the perfect setting for a romantic getaway, family gathering or memorable wedding.
Situated on a street with restaurants and coffee shops, this stylish all-suite hotel is a minute’s walk from the Museum of Culpeper History and a 15-minute walk from Culpeper Town Square.
Fountain Hall B&B is within walking distance to unique shops, casual and fine dining restaurants, Museum of Culpeper History, outdoor recreation, antiques, Visitors’ Center and Chamber of Commerce. Visit Civil War battlefields and historic sites of interest. Taste some of the finest Virginia wines while touring area vineyards. Play golf, hike, bicycle, or go horseback riding in the countryside.
We are Culpeper’s choice for any event, and we have designed the Culpeper Center to make event planning simple, which also includes hotel accommodations. Our hotel has state-of-the-art luxuries that you won’t find in a chain, and our attention to even the smallest detail makes this a can’t-miss hotel. We have suites that can accommodate everyone from the curious tourist to a large bridal party, and all who stay will be astonished by the level of comfort.


Air BnB in Charlottesville 

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Our guesthouse is located in the prestigious Ivy neighborhood of Charlottesville, Virginia overlooking the stunning Blue Ridge Mountains. We’re within a 10-minute drive to The University of Virginia and downtown Charlottesville and a 15-minute drive to the Nelson 151 winery, brewery, and cidery tours. We’re group and family friendly (pak-n-play available) and can help you arrange the perfect getaway, from helping with a wine tour to finding the right parking spot for UVA events. 
 Our new log home that sleeps 4 is located on 10 acres with beautiful mountain views! We look forward to welcoming you! Since we do live next door, we can easily be reached if any need arises. We have two horses, a donkey, and some chickens and love to tell all about them if you would like! Come visit our cozy log cabin with mountain views, near wineries and breweries, wedding venues, Shenandoah National Park, and Charlottesville.
Quiet rural setting close to vineyards, wedding venues, downtown Charlottesville and Monticello, Upfront has five bedrooms sleeping 12, 3.5 baths, an in-ground pool, three acres of lawns, horses in adjoining pastures and a small pond. We only book 6 months out.There are five bedrooms, two upstairs, one with queen and crib, one with twins. The two share a full bath. Downstairs, the front master has a queen, the back master also. Both have full baths. The Florida room has a queen sofa/sleeper and there’s a queen sofa/sleeper in living room. All together the house sleeps twelve.

Our place is close to The Wintergreen Ski Resort, Golf Club, Wintergarden Pool and Spa, restaurants and dining. Use our mountaintop retreat to relax and unwind, and enjoy our big dining room table, high ceilings, and tons of natural light. Galileo is great for families (with kids) as well as big groups.

Welcome to Féileacán, (Butterfly in the Irish Language) our Euro-Style four bedroom Home is comfortable, clean. It is very spacious and bright. It’s the perfect house for those wishing to entertain family or friends while in town. We are centrally located in the Fry Springs area of Charlottesville. With three full baths and a half bath on the main floor, it is a wonderful accommodation for 6-10 people.

West Park Gardens: Private guest room with comfortable king-size brass bed and a great view of the garden. Wake up to fresh coffee and a continental breakfast. Room shares a full bath with Queen Room. Located in a safe neighborhood, West Park Gardens is a short walk to popular E. Davis Street shopping and dining. Convenient to Blue Ridge Mountain hiking, wineries, equestrian events and historic sites. Last-minute getaway bookings are welcome. Early check-in upon request.

3 bedroom home in historic Virginia neighborhood. Great for family or couples getaway. Sleeps 6 comfortably. Full use of house with kitchen, living, dining, sun room and “secret garden”. Pet friendly.

Located on a dead-end road with only local traffic, enjoy the peace and tranquility this home has to offer with an easy drive to Charlottesville or Richmond as well as DC. With approximately 2100 square feet, you will be able to spread out comfortably! We are about 21 minutes to UVA Grounds/”The Corner” and 18 minutes to Downtown Charlottesville.

Our place is a perfect spot for gathering in a small group as well as also getting some quiet down-time in. The home is perfect for relaxing on the back deck and watching the deer visit as well as other wildlife. The backyard has a swing set with swings and slide for the kids or the young at heart! Take a stroll or a run on the dead-end road with only local traffic. You may even see the sheep on the private farm at the end of the road! (There are no street lights as we are in the country!)

A peaceful pocket of sanity. Stretch your wings & soak in fresh air, water, stars, mountains, pastures & wildlife. COVID clean w/Central HVAC UV air cleaner. Gen5 WIFI, in-house telescope, fire pit, gas grill. Early Mt. Winery, Bald Top Brewery, fine & country dining, SNPark hiking all w/in 7 mi. Historic sites in Orange, Culpeper and Charlottesville w/in 30 minute drive. Be sure to visit my regional Guide Book. Base price is for 4. Additional rates for guests 5-8. Long term rates discounted.

The space: 2 level contemporary home, great for bridal parties and showers, meeting in the middle, family reunions, girls’ getaways. The living room offers ample space for distancing, lounging or gathering. A large yard contains a fire pit. It is a perfect spot for small groups; friends, family holidays, retreats, girls getaways, small wedding parties and reunions. There is ample parking. “Signals” are spotty in neighborhood depending on topography. Verizon or Sprint service work best. GPS is spotty. We provide detailed directions for going Over Yonder. WIFI at the house.