The Best Historic Estate & Mansion Wedding Venues in Winchester, VA

Nestled in the heart of Virginia Hunt Country, Sylvanside Farm is a romantic wedding venue unlike any other. Established in 1744, our 25-acre property feels like a small European countryside village, featuring historic stone barns, sweeping gardens, a peaceful pond, and breathtaking open pastures. Couples love our seamless event flow, beautiful rain plan, and extensive included décor and furnishings that make planning easier and more affordable. From cocktail hour in our historic Stone Barn to receptions in the stunning Poplar Barn, every corner of the farm was designed to create an unforgettable guest experience. With timeless charm, flexible packages, and the ability to bring your own alcohol, Sylvanside Farm offers one of the best values in Northern Virginia while delivering a truly elevated wedding experience.

Greenock Manor is a 150 year old Farmhouse with towering giant trees. The Manor is a beautiful restored traditional American Victorian style farmhouse with a delightful wrap around balcony. We aim at a homely feel for our bridal families to reduce stress. We include a ton of props - so please visit us - we look so forward to meeting you. We set up the ceremony chairs for our couples as well as the tables and chairs for the reception area before you arrive for your wedding day to reduce stress. Any decor items you need are set up by us such as shepherd hooks, easels, signs and much more. We also include lawn games and we have a firepit for use to add extra ambience. Best part we are across the road from the nearest hotel so guests can walk to our venue AND up to 18 guests can sleep over at Greenock for the whole weekend - so many more happy memories. We can include a planner to manage your wedding on your wedding day too!

Located in the rolling hills of Maryland between Frederick, MD and Washington, D.C., Milton Ridge boasts exquisite setting and exceptional services. The beautifully restored Milton Ridge Historic Chapel and Reception Hall have been created exclusively for beautiful weddings and occasions with special attention given to every detail. Having your wedding ceremony and reception all in one location will make your wedding planning much easier. It gives you more control over timing and flow, as well as make things easier for your guests. At Milton Ridge, our event coordinator will assist in the planning of every detail of your wedding or special event. We have the ability to customize every detail to meet the specific needs for your special event. With our unique all-inclusive pricing, there are no surprises. You know the true costs up-front, which makes budgeting easier. It also allows us to offer beautifully personalized events at a tremendous value.

A breathtaking historic private mansion set amongst European style gardens in the Virginia countryside. Having everything available onsite makes your planning process as smooth and stress-free as possible possible.

Fox Meadow Barn is the the only event venue in Winchester, VA that will offer year round event rentals gatherings with climate control and plumbing amenities and the ability to be in an secluded field in the rustic atmosphere of a barn with exclusively your friends and family. Couples will have the luxury of a hotel, Walmart, Sheetz, 7-11, historic downtown Winchester which are all within a 2 mile radius. Services include, but are not limited to, weddings, anniversaries, birthday parties, work retreats, and essentially any gathering of people. We are committed to providing the highest quality venue in the Winchester, VA area.

The 1785 historical house, the modern pavilion, and a beautiful courtyard are all available for event rentals. The venue is accessible from the downtown walking mall. Enjoy your special day in luxurious history!

Looking for a spectacular place for your wedding? We can’t think of a better venue. We treat you as a unique individual with a unique style, and everything we do is geared towards that end. From the lush lawns with a choice of ceremony locations to the Grand Portico with its columned facade, to the rustic elegance of the Carriage House, we can offer you endless possibilities to design your special celebration. With overnight accommodations for up to 83 people, your closest friends and family can stay overnight at Rosemont and extend the festivities for multiple days of memory-making and fun.