The Best Wedding Venues in Saint Leonard, MD

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.

Serenity Farm is a place where history, nature, and celebration come together in a way that feels both timeless and deeply personal. Set along the quiet, scenic shores of the Patuxent River, the farm offers couples a wedding experience rooted in authenticity—rustic charm, historic character, and sweeping waterfront views that make every moment feel unforgettable. For couples seeking a venue that is beautiful without being pretentious, elegant without being artificial, and naturally romantic without needing heavy décor, Serenity Farm stands out as one of Southern Maryland’s most captivating wedding locations.

Flora Corner Farm, a working farm in southern Maryland, offers a tranquil setting for weddings and parties. Just 1.5 hours from Washington D.C., Annapolis, and Virginia, the farm features fields of soybeans, corn, and sunflowers, providing a beautiful backdrop for both barn weddings and intimate garden ceremonies. Perfect for smaller events, FCF can also accommodate up to 130 guests on its lawn. Recent bride Jessi K raves about the farm and its owners, praising their dedication and attention to detail in creating a perfect wedding experience.

Originally named St.Mary's Rectory this property was inducted into the National Register of Historic Places in 1987 and remains true to it's original mid-19th-Century appearance.Nestled in the quiet corners of Aquasco,MD. Roselynn Manor is the perfect destination for your dream event. Boasting 5 acres the property is rich in legacy dating back to 1849 making it a cherished landmark into ur community.

For over 30 years, Herrington on the Bay has transformed waterfront dreams into unforgettable wedding realities. We know you'll be captivated by our panoramic Chesapeake Bay views and our delectable, locally-sourced menus. But what truly sets us apart is the unparalleled service we deliver. When you choose Herrington's full-service wedding package, we take care of everything: the venue, planning and coordination, exquisite food and beverage service, attentive staff, and stunning on-site amenities. We'll also collaborate with you to craft a customized menu featuring sustainable ingredients from our trusted partner farms. Let Herrington on the Bay orchestrate your luxurious waterfront wedding, a celebration as exquisite and unforgettable as your love story.

We are a place where you can express your unique vision and bring your wedding dreams to life. There are a few different ways to celebrate your wedding weekend here at Wylder. Depending on headcount and date availability. From intimate waterfront escapes to extravagant weekend-long festivities, we have the perfect package for you! We have over 9 acres of lush grounds, 50 hotel rooms, 1100 feet of private waterfront & over 4,000 sq. feet of indoor & outdoor waterfront flexible event space for you to plan the custom wedding of your dreams! * Hotel rooms are booked by your guests *

Host your next unforgettable event at Marcellus Farms™, where elegance meets nature. Whether you envision a grand gathering in Manor En Noire, a rustic yet refined celebration in our Luxe Barns, or an open-air experience with our Outdoor Rentals, we offer versatile spaces tailored to your needs. From intimate gatherings to large-scale events, our estate provides the perfect setting for weddings, corporate retreats, and special occasions. Book your venue today and bring your vision to life!

The Anchorage, with origins back to 1800, is a venue set on 12 private acres with waterfront views situated on the beautiful Choptank River. We offer a relaxed, peaceful and romantic experience on the shores of the river, which is part of the Chesapeake Bay waterway. The venue includes an open air, covered pavilion with spectacular waterfront views for up to 100 people.

Welcome to Swan Point Yacht & Country Club, the ideal venue for your dream wedding. Nestled on the serene shores of the Potomac River, our charming venue provides a stunning backdrop for your special day. Our experienced team is dedicated to bringing your unique vision to life. Exchange vows in our picturesque outdoor ceremony site, with panoramic views of the Potomac River and lush green surroundings. Transition to our elegant reception venue for a stylish celebration with your guests. At Swan Point Yacht & Country Club, we ensure a stress-free and memorable wedding day. Our attentive staff will guide you through every detail, allowing you to relax and cherish the moment. Whether it’s a grand celebration or an intimate gathering, we offer the perfect setting for your dream wedding. Contact us today to explore customizable wedding packages and start planning your perfect day.

A gorgeous wedding venue just minutes from Annapolis. The Golf Club at South River is a unique golf club and wedding venue located in Edgewater, Maryland. Located just minutes from Annapolis, The Golf Club at South River offers a perfect blend of rustic and modern elements set against a lush and scenic backdrop. From the spectacular views to the lavish furnishings, The Golf Club at South River could be the perfect place to celebrate your dream wedding day. Our catering team, offers custom menu selections for plated, buffet and culinary station style events. Enjoy a signature cocktail, hors d’oeuvres, creative culinary stations, a rustic-style buffet, or an elegant plated affair at your reception. We look forward to guiding you through the process of planning your once in a lifetime occasion!

Hemlock Farm is the perfect rustic venue for a beautiful summer wedding. Known for its stunning weddings and annual Christmas tree selection, this charming farm offers a warm and welcoming atmosphere. Weddings take place in front of the picturesque red barn, surrounded by family and close friends. Hemlock Farm also offers the freshest fir Christmas trees and greenery, making it a family-friendly destination year-round. Celebrate your special day in a setting that combines rustic charm with heartfelt hospitality at Hemlock Farm.

Imagine exchanging vows with the Chesapeake Bay as your backdrop, surrounded by lush landscapes and the charm of a living shoreline. The Annapolis Maritime Museum offers a unique and picturesque setting in America’s Sailing Capital, where you can host your special day right on the water. Enjoy stunning views, an affordable venue, and a true taste of Annapolis. The Annapolis Maritime Museum & Park boasts 2 uniquely charming waterfront wedding venues. The Maritime Museum: located in the Eastport neighborhood of Annapolis, the former McNasby’s Oyster Company building offers outdoor ceremony and indoor reception space with a uniquely Chesapeake Bay vibe. The Park Pavilion: located within our 12-acre park campus along the scenic shores of Back Creek, offers a rustic stone amphitheater ceremony space with an open-air Pavilion reception, that includes a working stone fireplace. The Annapolis Maritime Museum is the coastal venue of your dreams- where history meets the harbor.

If you’re visiting this page, chances are you’re planning the most important day of your life! First off, please accept a resounding congratulations from the entire team at Chesapeake Bay Beach Club. For over two decades, we’ve been journeying alongside couples and their families as they plan for this joyous occasion, and we’d be bluffing if we said it wasn’t our absolute favorite thing in the world! A stunning, coastal Maryland backdrop ideal for your dream wedding, we cordially invite you to plan your very special day with us at Chesapeake Bay Beach Club! With four fantastic venue options to choose from (each of which brings its own unique distinction), the custom-curated, Chesapeake Bay wedding of your dreams is within reach like never before! Select from our array of remarkable spaces as you plan not only your wedding ceremony, but also your splendid rehearsal dinner, celebratory reception, cheery bridal luncheon, and more!

Immerse yourself in unmatched elegance and charm at the Queen Anne Event Center, nestled within the breathtaking Hyatt Place Kent Narrows & Marina, where every detail is thoughtfully curated to surpass expectations and create enduring memories against the backdrop of stunning waterfront vistas. Elevate your next gathering, wedding, or conference with our versatile 4,000 square feet of indoor meeting and event space, perfectly suited for both professional and social gatherings. Step outside onto our 3,000 square feet of additional patio space, offering picturesque views that enhance any outdoor event. Whether accommodating up to 150 guests in our expansive Queen Anne Ballroom or hosting intimate gatherings in our stylish Meeting Room or the Narrows Boardroom, our venue is designed to meet your every need.

With over 115 acres of land just 15 minutes from downtown Annapolis, the property is set on a mile and a half of Chesapeake Bay shoreline. The beautifully and lovingly restored National Historic Landmark offers an unparalleled backdrop for your one-of-a- kind wedding or private celebration.

Wildflower Estate is where luxury meets love. Offering both venue-only and all-inclusive packages, our Maryland Eastern Shore estate pairs chic design with lush landscapes. Whether you want a fully planned wedding or the freedom to craft your own, we provide the perfect backdrop for a celebration that’s effortlessly stylish and uniquely yours.

The Osprey's at Belmont Bay is a charming waterfront venue filled with natural beauty and a laid back luxury. With the picturesque Occoquan River providing a naturally breathtaking backdrop, the venue features a beautifully adorned ballroom and spacious accommodations for up to 146 guests. Our outdoor ceremonies are truly enchanting with a flagstone aisle leading to a pergola framed by a beautiful waterfront view.

Step foot in our luxury hotel in Washington D.C. and discover an urban resort located along the banks of the Potomac River. Here, you’ll uncover a hotel unlike anything in Washington D.C. — a place where modern design blends with an iconic landmark to redefine luxury. The Watergate Hotel's flowing avant-garde architecture was designed by Luigi Moretti to emulate the mighty Potomac, and its stunning new Ron Arad-designed interior lives up to the building's original elegance. Complementing the hotel's new, modern feel are the retro-chic staff uniforms, made by Mad Men costume designer Janie Bryant. The Watergate Hotel takes classic elegance and bold mid-century modern design and adds all of the extravagance and warmth of contemporary luxury. This one-of-a-kind hotel pays tribute to its own storied past, while paving the way for a new chapter to be written.

At Top of the Town, your wedding is more than an event—it’s an experience your guests will remember long after the night ends. Perched above Arlington, our penthouse venue offers sweeping, unobstructed views of Washington, DC—from the Capitol and Washington Monument to the Lincoln Memorial and beyond. As the sun sets and the city lights begin to glow, the space transforms into something truly unforgettable. Designed for couples seeking a unique and elevated experience, Top of the Town features both indoor and outdoor spaces for your ceremony, cocktail hour, and reception to flow seamlessly from one moment to the next. We comfortably accommodate up to 180 guests cocktail-style and 150 seated. We provide the essentials—including tables, chairs, a spacious dance floor, and a private outdoor terrace—while giving you the flexibility to bring in the catering and personal touches that reflect your vision. We’d love to welcome you for a tour and show you the view in person.

Welcome to Harbour View — where we make your dreams a reality. Every year we host hundreds of weddings and special events located right on the Occoquan River. With its contemporary, neutral décor and breathtaking river views, Harbour View blends a rich luxurious feel with the natural beauty of a waterfront setting. If you’re looking to put on an elegant affair with a guest count of 10 to 300 guests, you’ve come to the right place.

Farm 1750 has reimagined our historic farmhouse into the perfect Virginia Countryside Wedding Venue. Established in 1750 this working farm has endured through generations and awaits you and yours. Start your legacy today at Farm 1750 Novacelli means New Barn in Porteguese - our amazing barn has retractable walls and ceiling so you can create the perfect venue location for your special day. Historic Farmhouse Charm Prepare for your wedding day in an authentic farmhouse built in 1750. All the character retained, but no modern comfort spared.

Family-owned, boutique, Virginia farm winery, serving delicious, award-winning Virginia wines. Both our Stables and Dairy Barn tasting rooms are fully handicap accessible. No reservations are needed or required for our tastings. We have ample seating provided! We are a family & pet-friendly winery! Yes! Your fur baby is welcome inside our tasting rooms, as long as they are well-behaved and on a leash. Look for fun food trucks, pop-up sips and shops, amazing bands, and some of the most fantastic, authentic Spanish Sangria you have ever tasted in your life. Plus, delicious wine slushies too!

Our waterfront wedding venue lets the Chesapeake Bay provide a beautiful and elegant backdrop to your special day. Our goal is to exceed your expectations right down to the smallest detail because your wedding deserves no less. Our 30 years of experience planning all-inclusive weddings means that your journey can be stress-free. From relaxing in your bridal suite to photos on the waterfront, to dancing the night away – your day will be perfect! Consistent quality and diverse variety is the hallmark of our wedding catering service. Whether looking for an elegant multi-course dinner, or lighter afternoon fare, our extensive selection ensures you’ll find the perfect menu to compliment your event.

Swan Point is a boutique waterfront venue designed for intimate weddings with 50 or fewer guests. Set along the Occoquan River, our gazebo and natural surroundings create a peaceful, romantic backdrop. We specialize in small celebrations that feel personal and elegant—never crowded or rushed. Our space is ideal for couples who value simplicity, aesthetics, and a relaxed experience. Please note: we do not accommodate events above 50 guests.

The Anchor Inn is a private waterfront wedding venue in Pasadena, Md. With only one wedding on the property at a time, Anchor Inn is the perfect intimate reception and ceremony site for your wedding. Steps away from the Chesapeake Bay, this venue sets the ambiance for a perfect day with friends and family. With a beautiful pier and covered ceremony options, you and your guests will be surrounded by the beauty of the Chesapeake Bay for your entire event. You'll also get stunning views of the Bay Bridge as well! If you’d like a free visit and consultation, please contact us today!

The Inn at Osprey Point is a sprawling estate in the charming village of Rock Hall, Maryland. This premier wedding venue and B&B is surrounded by 30 acres of lush landscapes and spectacular water views. It offers a variety of beautiful settings for any wedding day. The colonial-style inn caters to intimate celebrations while a one-of-a-kind waterfront tented reception will charm guests and loved ones. Whatever classic coastal vision couples have for their special day, the Inn at Osprey Point can make dream weddings come true. Please reach out for the full wedding package including food and bar choices that are available. With catering, bar, a full staff, and day-of coordination, your wedding is bound to be stress-free with Osprey Point!

Swan Cove Manor is a 5 house waterfront estate on the eastern shore of Maryland. We host 3 night weekend celebration and can accomadate up to 70 people. We include a lot in our wedding package with additionals services that can be offered. Swan Cove Manor is your private waterfront estate for a spectacular wedding weekend on the Eastern Shore. Situated on 20+ scenic acres, this "one of a kind" property offers unspoiled natural elegance against the stunning backdrop of the Chesapeake coast. Couples can celebrate for an entire weekend, utilizing five spacious, designer-furnished manor homes for lodging and preparation. Imagine your ceremony on the waterfront followed by a grand reception tailored to your unique vision, from casual to formal.

Nestled in the charming bayside town of Chesapeake Beach, MD, the Rod N’ Reel Resort blends contemporary coastal elegance with effortless convenience. This waterfront retreat offers a perfect backdrop for your celebration, featuring luxurious beachside venues and modern ballrooms designed to feel anything but traditional. From onsite accommodations to an array of dining experiences and late-night indulgences, your guests will enjoy comfort, style, and entertainment all in one place. To make your vision a reality, the Rod N’ Reel Resort provides wedding amenities, from onsite catering to bar service by our culinary team. Our dedicated wedding specialists are here to guide you every step of the way—from crafting timelines and floor plans to providing seamless support on your wedding day! Quietly tucked along the Western Shore of the Chesapeake Bay, the resort feels like a serene destination getaway—yet it’s less than an hour from Washington, D.C. and Baltimore.

Dawn On the Chesapeake is an exquisite outdoor venue designed for elegant events. Nestled along the waterfront, our location exudes intimate and romantic charm, perfectly complemented by a stunning Mediterranean-style mansion that serves as both a picturesque backdrop and the home for our spacious getting-ready suites.

We're a blank slate and host weekend weddings, so estimates given are for Friday - Sunday morning. We also have 15 years experience and know how to help with all the details. Our point is surrounded by miles of water, with sunrise over the Choptank River and sunset over the Chesapeake Bay. We have no neighbors, no cut-off times, and we customize our weddings using our local vendors. We have no hidden fees. We set up meetings with your vendors and you pay them directly. Because we have one of the most unique locations, we had hosted some of the most unique weddings guests have ever attended. The privacy of our point ensures the freedom to make your day as special as you are as a couple. And with plenty of time, there is no rush enjoying the point with your friends and family.