Lodge and Retreat Wedding Venues in Chester, VA

Cary Hill 1741 is an itimate and historic location with modern touches, creating a unique and ecclectic vibe. Our style is relaxed, with very few "requirements" so that you can create your celebration the way you want it to be.

Avon Hill is a laid back, luxurious wedding and vacation destination in central Virginia. We offer your choice of beautiful outdoor ceremony locations, a newly opened barn with all the modern conveniences, and lodging for up to 43 of your closest family and friends. Beautifully appointed bride and groom suites are included for your wedding and each wedding package is for a full weekend of property access.

Over 300 reviews reveal our secret-historic hand-hewn stone and timbers are complimented by views, spaciousness, and flexible options for your style. The top (reception area), bank (cocktail area or rain ceremony option), and bridal cottage are apparent, but the scope of vistas, privacy, and proximity to town are unique to Cloverdale Barn, and provide the value you and your guests will remember.

Camp Holiday Trails is a beautiful 70+ acre nonprofit camp located in the foothills of the Blue Ridge Mountains. Open year-round, we engage children and teens with medical needs. Special event and wedding rentals support our inspiring mission. Many joyful, loving, fun and playful weddings have taken place with us and the wedding weekend with lodging is a favorite "wedding destination" package of choice.

Make your wedding a historic event at B&B Inn, a historic property with mountain views in Middleburg – the heart of Virginia horse and wine country. With our 47 acres, beautiful grounds, lodging, & event building for up to 200, we are an ideal venue for your wedding. Conveniently located, Briar Patch is just 20 minutes from Dulles Airport and about an hour from Washington, DC. Hold your rehearsal dinner around our pool. Have your ceremony overlooking the mountain or under a 200 year old tree. Celebrate with a reception in our indoor facility for up to 200 guests using any caterer you choose. Have your guests stay in one of our 8 rooms in the main house, in our one-bedroom cottage, or in the 3-bedroom chicken coop. Your wedding at Briar Patch Bed & Breakfast Inn will provide you the opportunity to spend quality time together. Our outstanding accommodations, breathtaking country setting, and exceptional service are what set us apart from other wedding and reception sites.

Trump Winery is the venue where your wedding dreams come true. Whether you’ve envisioned an extravagant event or an elopement for just the two of you, we promise to create memories that you and your loved ones will cherish forever. Our 1300 acre property is nestled in the foothills of the Blue Ridge Mountains, conveniently located 20 minutes from downtown Charlottesville. Our grounds have picture-perfect rolling hills, lakes, and over 200 acres of vines. Trump Winery couples benefit from indoor and outdoor ceremony, cocktail hour and reception settings, in well-appointed, heated and air-conditioned, luxury venues. Less than a mile away from both the Barn & Pavilion and the Grand Hall is our Albemarle Estate at Trump Winery, a 26,000-square foot, 11 bedroom mansion that provides overnight lodging for guests and a honeymoon night option for couples.

Set on Grelen Nursery's 600-acre tree nursery, The Market at Grelen is a magical wedding venue boasting rural simplicity at it’s most luxurious! It has gorgeous 360-degree views and was lovingly designed to emphasize the surrounding natural beauty. Perfect for the creative party planner, The Market at Grelen has a variety of event spaces: a greenhouse, a shade garden & berry field, a large bluestone terrace, a 4500 sq. ft. clear stargazing tent and a groomed pasture at the highest point of the nursery. ​Located in Central Virginia (only 35 minutes north of Charlottesville, one hour west of Richmond and two hours south of DC), it is PERFECT VENUE for a variety of celebrations. LGBTQ+ friendly.

Celebrations at The Manor are one-of-a-kind events designed to tell your story. Whether it's a wedding weekend surrounded by 150 of your closest family and friends or simply a weekend away with a few friends to celebrate a birthday, The Manor offers the perfect setting. Nestled in the heart of VA's wine country on over 18 acres there are multiple indoor and outdoor locations to accommodate your event. The Manor at Airmont has multiple sites for ceremony, cocktail hour, and reception. Our venue offers an in-house design team and catering, and event planning and management options.

CountyLine Vineyard & Venue is an off the beaten path wedding venue set in the countryside of central Virginia. Shortly down the lane in view are a picturesque venue barn, vineyard, pre-civil war log cabin, and fields offering beautiful backdrops for a wedding ceremony, reception, and photographs. Artistic wood features abound throughout the barn. Much of the wood, harvested right from the property, was meticulously shaped by hand to add a warm artistic feel to the spaces within. Along with a 2,000 square foot banquet room, there's a bridesmaids get-ready suite, caterer's prep room, restroom facility, and an outdoor bar and patio areas. Also located on the property is a pre-civil war log cabin available for overnight accommodations for event guests. The peaceful country setting offers many other options if you choose to celebrate your special day with an outdoor ceremony and reception.

The Keswick Hunt Club was founded in 1896, and the building with its 2018 renovation can host wedding receptions, engagement parties, rehearsal dinners, and every special celebration. Recently renovated the building now has modern amenities that will provide your guests much comfort while enjoying the beautiful Virginia countryside. The entrance and restrooms have ADA accommodations, new HVAC for all seasons, additional new dining space, and a new modern catering kitchen for your favorite caterer. The wrap around porch can be used for cocktail receptions or provide additional seating if needed. A stone patio has been added adjacent to the porch to enjoy the Virginia countryside. The main dining room has an elevated stage for your band to play and for your toasts to be given on your happy occasion.

Escape to the beautiful Virginia countryside and celebrate all weekend long at Tranquility Farm. Our boutique venue offers a relaxing 48-hour experience and stunning indoor and outdoor spaces, perfect for staying safe. Make the farm your own and host all festivities here, including rehearsal dinner and brunch. Enjoy luxurious accommodations for 16 guests for two nights. Our Antique Barn has been updated with climate control, bathrooms & catering kitchen. Nestled in D.C.'s wine country, the farm is convenient to Dulles Airport.

Monroe Bay Vineyard is located on the water near Colonial Beach on the original birthplace Farm of our 5th President James Monroe. We have secluded and tranquil waterfront land to plan your perfect day. We have a large, unique barn made of natural, recycled materials of strawbales for insulation and recycled wine bottles for light and design. You no longer see the strawbales in the wall as they have been covered with a hydraulic lime the same material castles in France for hundreds of years have been made from. The inside is a museum quality white lime finish with unique curves with sun shining through the patterned wine bottle walls to give a unique backdrop.