The Best Vineyard & Winery Wedding Venues in Little Orleans, MD

The Best Vineyard & Winery Wedding Venues in Little Orleans, MD

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8 Wedding Venues in Little Orleans, MD

Vineyards, wineries
150-200 guests
Available on May 30, 2026
Quick responder
Milton Ridge 

5.0

  • Up to 150 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $3,250
  • Offer

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.

Why you'll love this venue

  • Has onsite accommodations
  • Classic, vintage atmosphere
  • Provides lighting and sound

Venue considerations

  • Not for you if you are looking for something nontraditional
  • Not for you if you don't want a rustic vibe
Awarded Best of Zola
My daughter and her husband chose Milton Ridge for their wedding venue. I live on the opposite coast so I had no opportunity to have a look myself. She and her husband were very happy with the layout of the property and the location. She assured me that staff were warm and friendly as well as very professional and that all questions were addressed promptly and in great detail. My daughter and her husband felt listened to and respected by everyone at Milton Ridge. I was anxious but it was their wedding and they had done a lot of research! I am overjoyed that they chose Milton Ridge for their very special day!! I spoke to many guests and family members that day and evening; everyone had high praise for the couple’s choice of venue. The property is self-contained with a beautiful turn of the century chapel on the lower level of the property and a very large bricked patio on the upper level; with an enormous wooden gazebo at one end and tiered garden area at the opposite end. Indoor or outdoor wedding?? Hard to choose as both areas are sooooo lovely. The Bridal suite and Grooms quarter are in a building adjacent to the chapel on the lower level of the property. Another turn of the century building with Bridal suite, porch and porch swing on the ground level and the Grooms quarters on the 2nd level via a private enclosed stairway; providing total privacy for both parties and their respective entourages. Both areas were very well appointed, comfortable and large; plenty of room for multiple people in each area to get ready for the big day! The Reception Hall was on the upper level with a porch and short stairway leading from the hall to the outdoor patio. The Hall was fresh and bright with plenty of room for DJ, tables, dance floor, bar and buffet without feeling overfilled or crowded. Bride and Groom chose the bar-b-que menu for their dinner; it was beautifully presented, delicious and plentiful. No one left Milton Ridge hungry that evening! The wait staff and bartenders were all very attentive and had obviously been very well trained at table service and bar service respectively. Music was provided by a DJ who was contracted by Milton Ridge and was included with the package that my daughter and her husband had chosen. The selection was a mix of old and new with the focus of getting the guests up and dancing. He was very good at his job and he accomplished his goal! Last but definitely not least; the photographer; also contracted with Milton Ridge! He was amazing!!! The unique shots, quality and beauty of his work left us speechless. He was everywhere, but never in the way, always inconspicuous and watching for that perfect candid shot. Even his posed photos had a very relaxed casual look about them. All photos were organized and available to the newlyweds on the Milton Ridge website within 10days of their wedding day!! ALL pictures belong to her and her husband to print, copy and share with whoever they wish!! Milton Ridge exceeded my expectation and I would never hesitate to recommend them to anyone!!
Karen F., 7 months ago
Breaux Vineyards 

5.0

Purcellville, VA
  • Up to 150 guests
  • Select services
  • Indoor & outdoor
  • Starts at $5,000
  • Offer

Breaux Vineyards, nestled 'between the hills' of Short Hill and the Blue Ridge Mountain in western Loudoun County (15 minutes from both West Virginia and Maryland), is one of the most desired destinations in Northern Virginia wine country for an elegant vineyard wedding. The 404 acre estate boasts panoramic beautiful views of rolling vines and mountain landscapes, and is sure to offer the most picturesque background for your most memorable events. Our expansive private outdoor ceremony setting and sparkling crystal chandeliered ballroom, with windows spanning three sides, will leave guests talking for years to come!

Why you'll love this venue

  • Flexible event spaces
  • Offers a sense of luxury
  • Multiple event spaces

Venue considerations

  • Does not provide event staff
  • On-site parking not available
  • Limited cleanup and setup services
Breaux was the most beautiful venue for our wedding! It was extremely welcoming for a queer wedding and we enjoyed working with Robin and Jordan. The venue was well-organized and had great suggestions for local vendors to work with. We wound up really appreciating their mandatory final walkthrough with our caterer and coordinator - it made us feel much better about the flow of the wedding on the day of. They let us supply our own non-wine alcohol, which helped us manage costs. We would highly recommend them!
Sarah L., 2 months ago
Quick responder
Kalero Vineyard, LLC 

5.0

Hillsboro, VA
  • Up to 150 guests
  • Select services
  • Indoor & outdoor
  • Starts at $4,500

Kalero is a lovely 130 acre farm and vineyard, located in western Loudoun County with breathtaking views of the Blue Ridge mountains. Our historic barn, the cornerstone of which was set in 1834, has gone under extensive restoration to become one of Loudoun County’s premiere wedding destinations, and soon to be tasting room. The barn has been fondly nicknamed Heartstone Barn – in honor of a unique heart-shaped stone discovered on the property by our daughters. Heartstone Barn is the perfect choice for those seeking a rustic yet elegant space to host a wedding or corporate event. We offer 2,500 square feet, and can seat up to 150 guests on our main floor with additional space found in our two lofts. We also provide a changing suite, a large stage, and catering space. If you are looking to host a larger outdoor event, Kalero offers plenty of open space options for any special occasion you may have in mind.

Why you'll love this venue

  • Bridal suite on site
  • Unique barn setting
  • Flexible event spaces

Venue considerations

  • No venue-provided food services
  • Not wheelchair accessible
  • No built-in audiovisual options
I had my wedding at Kalero on 10/13/25. From the start, Ann was extremely responsive. Any questions I had was given a response within the day. She was willing to work with us for anything we needed The venue itself is gorgeous!! From the vineyards, the views, the barn reception area… it’s so beautiful outside and so cute inside. I truly didn’t feel like I had to go overboard with decorations, as the place itself great. I highly suggest touring the venue, it’s SO worth it!
Brianne H., 2 months ago
Shiloh Manor Farm 

5.0

Purcellville, VA
  • Up to 150 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $5,500
  • Offer

Shiloh Manor Farm is a hidden gem where rustic charm meets timeless elegance. As a historic landmark rich in history, our breathtaking five-acre property offers an intimate and enchanting setting for weddings, private celebrations, and special gatherings. With a charming barn, a serene pond, a picturesque gazebo, and a small vineyard, every corner of our venue is designed to create unforgettable moments. And as the day turns to evening, prepare to be awed—the sunsets at Shiloh Manor are simply breathtaking, painting the sky with hues of gold and crimson. Whether you envision an elegant soirée under the stars or a cozy, intimate affair, Shiloh Manor offers the perfect blend of romance, sophistication, and countryside charm. Let us bring your dream event to life in a setting as beautiful as your love story.

Why you'll love this venue

  • Handles all cleanup logistics
  • Flexible event spaces
  • Provides event staff

Venue considerations

  • No free parking
  • Not for you if you're looking for a sleek and contemporary space
  • Dance floor not included
Shiloh Manor Farm was the perfect venue for our wedding. From the moment we first spoke with the team, they were friendly, welcoming and intelligent in their approach. The venue itself was excellent - roomy, welcoming and exactly what we were looking for. On the day of our wedding, the staff provided perfect service with a great personality, ensuring our special day went off without a hitch. We are so grateful to the team at Shiloh Manor Farm for helping to make our wedding truly unforgettable.
Deborah L., 8 months ago
Quick responder
The Manor At Airmont 

5.0

Round Hill, VA
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

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.

Why you'll love this venue

  • Classic, vintage atmosphere
  • Has a dance floor for celebration
  • Provides a dedicated team on-site

Venue considerations

  • Not for you if you don't want a rustic vibe
  • Not wheelchair accessible
  • Not for you if you are looking for something nontraditional
The Manor at Airmont is an absolutely stunning venue resting in the mountains of Round Hill, VA. They are an all-inclusive venue with a team comprised of mostly family. From start to finish, the team catered to our interests and really focused on creating a wedding that was memorable and unique to us. Every single member of the Manor team was so friendly and professional and made us feel extremely special. It was so nice giving a general vision to wedding planner Natallia and seeing what she and her team came up with to bring it to life...and boy did they DELIVER. They gave us the maximalist, royal court wedding of our dreams! Guests were blown away by the decor and people are still raving about the amazing food created by Zesty Gourmet. It was such a beautiful experience throughout and guests still call me up to tell me it was the BEST wedding they have ever been to. The best part? We planned our wedding with the Manor in just under a year with ZERO stress. We had numerous meetings to make final decisions on decor and food, but they made it the most fun year of engagement bliss without any of the wedding planning stress. The perfect wedding for a perfect end to our perfect year. WE LOVE THE MANOR AT AIRMONT!
Victoria R., a month ago
Quick responder
West Oaks Farm Market 
Winchester, VA
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $5,000

We are a rustic farm venue with sights of apple orchards and rolling hills of our 200-acre farm. Our venue offers the beautiful country setting along with our elegant banquet room featuring a spacious reception space paired with wooden ceiling beams, ceiling-height fireplaces, rustic wooden trim, luxurious bridal suites, and restrooms for your guests. West Oaks Event Center accommodates large and small gatherings seeking country views with a modern and comfortable interior reception space. Multiple ceremony site options cast views of the gorgeous Shenandoah Valley to the south. Our venue is the perfect location for your special day to share with your loved ones and leave them remembering the beauty of our area for years to come.

Why you'll love this venue

  • Allows pets
  • Surrounded by beautiful vineyards
  • Provides setup and cleanup

Venue considerations

  • On-site parking not available
  • Not for you if you prefer a more modern aesthetic
  • Large venue, not ideal for small guest lists
Quick responder
Boulder Crest Estate 
BLUEMONT, VA
  • Up to 200 guests
  • Raw space
  • Outdoor & indoor
  • Starts at $8,000

For Those Who Desire Nothing Less Than Extraordinary. Boulder Crest Estate is located an hour west of Washington DC nestled on 134 acres, our timeless estate—originally built in the early 1900s—offers the perfect blend of historic charm and natural beauty, a wedding setting unlike any other. Impeccably manicured gardens, sweeping lawns, and breathtaking views that stretch all the way to Washington, D.C., Every detail of the estate speaks to grace, elegance and sophistication, making it a dream backdrop for brides and couples seeking a truly unforgettable celebration. Boulder Crest Estate is ideal for weddings, exclusive corporate events, rehearsal dinners and luxe private parties, photoshoots and more,

Why you'll love this venue

  • Surrounded by beautiful vineyards
  • Raw space for complete customization
  • Flexible event spaces

Venue considerations

  • No built-in audiovisual options
  • Dance floor not included
  • Not wheelchair accessible

Location flexible? Discover venues near Little Orleans, MD

About wedding venues in Little Orleans, MD

Maryland offers exceptional variety for couples planning their special day. You can choose from Chesapeake Bay's waterfront settings with their shimmering views, explore Baltimore's historic mansions filled with ornate architectural details, or celebrate in Eastern Shore's rustic barns surrounded by pastoral landscapes that create a picturesque backdrop for your celebration.

What's the True Cost of a Maryland Wedding?

The price tag for Maryland weddings varies significantly based on guest count. Small gatherings of about 50 guests average $22,754 while mid-sized celebrations with 150 guests typically run around $51,712. Large weddings hosting 300 guests can reach $89,329. Your venue will likely be your biggest expense at about $8,532 for a typical wedding; that's 16% of your total budget for a 150-person celebration, so choosing wisely matters.

Which Maryland Regions Offer the Best Wedding Settings?

# Baltimore Area

Baltimore venues showcase the area's rich architectural heritage and stunning harbor views. The Belvedere features incredible gilded ceilings crystal chandeliers and grand staircases that create perfect dramatic entrances for your big moment. Celebrations at the Bay gives you panoramic waterfront ceremony spaces with dedicated sunset photography locations that'll make your album spectacular. You'll appreciate their customizable reception layouts that comfortably fit up to 250 guests so everyone has space to enjoy.

# Eastern Shore

The Chesapeake Bay region delivers quintessential Maryland beauty that your guests will remember. Chesapeake Bay Beach Club offers private beaches for your ceremony waterfront ballrooms with floor-to-ceiling windows and charming oyster shell pathways that reflect the local maritime culture. Castle Farm combines beautiful equestrian elements with thoughtful accessible design including solid-surface walkways and convenient golf cart shuttles so all your guests can participate fully.

How Much Should You Budget for Wedding Services in Maryland?

For a 150-guest wedding in Maryland, expect these costs:

ServiceAverage CostPercentage of Total
Venue$8,53216%
Catering$6,82613%
Florals$6,54113%
Bar Service$5,46111%
Photography$4,9069%
Videography$3,9118%
Wedding Planner$4,0538%
Band/DJ$1,7503%
Cake/Desserts$1,4013%
Hair/Makeup$7902%

When Should You Book Your Maryland Venue?

Most couples in Maryland secure their venues about 14 months before their wedding date. You'll want to plan ahead since December sees the highest inquiry volume when many newly engaged couples start their search. Keep in mind that summer and fall wedding dates often come with premium pricing, so if you're flexible with your date you might find better value in other seasons.

Where Can You Find Accessible Wedding Venues in Maryland?

Castle Farm Weddings offers truly inclusive spaces for all your guests. You'll find accessible ceremony and reception areas with no steps wheelchair-friendly walkways designated handicapped parking and ADA-compliant restrooms throughout. Ten Point Acres Venue can comfortably seat up to 500 guests with fully accessible facilities including large handicap restrooms and climate control for year-round comfort so everyone can focus on celebrating your special day.

What Are Maryland's Best Venues for Remote Participation?

Chesapeake Bay Beach Club provides stunning waterfront settings that enhance the virtual experience for guests who can't attend in person. You'll love their post-event storytelling approach that keeps remote guests feeling connected. Graduate Annapolis gives you advanced tech infrastructure for high-quality streaming with nautical-themed digital backdrops that help engage virtual viewers and make them feel part of your celebration.

Which Maryland Venues Feature Outstanding Culinary Experiences?

Valley Country Club set in a grand 1850s mansion offers all-inclusive packages with elegant butlered hors d'oeuvres and complete meal service that impresses even the most discerning guests. Their crab cakes are simply phenomenal and often receive rave reviews from attendees long after the event. You'll benefit from their over 70 years of hosting expertise that ensures everything from appetizers to dessert flows seamlessly.

Maryland offers exceptional variety for couples planning their special day. You can choose from Chesapeake Bay's waterfront settings with their shimmering views, explore Baltimore's historic mansions filled with ornate architectural details, or celebrate in Eastern Shore's rustic barns surrounded by pastoral landscapes that create a picturesque backdrop for your celebration.

What's the True Cost of a Maryland Wedding?

The price tag for Maryland weddings varies significantly based on guest count. Small gatherings of about 50 guests average $22,754 while mid-sized celebrations with 150 guests typically run around $51,712. Large weddings hosting 300 guests can reach $89,329. Your venue will likely be your biggest expense at about $8,532 for a typical wedding; that's 16% of your total budget for a 150-person celebration, so choosing wisely matters.

Which Maryland Regions Offer the Best Wedding Settings?

# Baltimore Area

Baltimore venues showcase the area's rich architectural heritage and stunning harbor views. The Belvedere features incredible gilded ceilings crystal chandeliers and grand staircases that create perfect dramatic entrances for your big moment. Celebrations at the Bay gives you panoramic waterfront ceremony spaces with dedicated sunset photography locations that'll make your album spectacular. You'll appreciate their customizable reception layouts that comfortably fit up to 250 guests so everyone has space to enjoy.

# Eastern Shore

The Chesapeake Bay region delivers quintessential Maryland beauty that your guests will remember. Chesapeake Bay Beach Club offers private beaches for your ceremony waterfront ballrooms with floor-to-ceiling windows and charming oyster shell pathways that reflect the local maritime culture. Castle Farm combines beautiful equestrian elements with thoughtful accessible design including solid-surface walkways and convenient golf cart shuttles so all your guests can participate fully.

How Much Should You Budget for Wedding Services in Maryland?

For a 150-guest wedding in Maryland, expect these costs:

ServiceAverage CostPercentage of Total
Venue$8,53216%
Catering$6,82613%
Florals$6,54113%
Bar Service$5,46111%
Photography$4,9069%
Videography$3,9118%
Wedding Planner$4,0538%
Band/DJ$1,7503%
Cake/Desserts$1,4013%
Hair/Makeup$7902%

When Should You Book Your Maryland Venue?

Most couples in Maryland secure their venues about 14 months before their wedding date. You'll want to plan ahead since December sees the highest inquiry volume when many newly engaged couples start their search. Keep in mind that summer and fall wedding dates often come with premium pricing, so if you're flexible with your date you might find better value in other seasons.

Where Can You Find Accessible Wedding Venues in Maryland?

Castle Farm Weddings offers truly inclusive spaces for all your guests. You'll find accessible ceremony and reception areas with no steps wheelchair-friendly walkways designated handicapped parking and ADA-compliant restrooms throughout. Ten Point Acres Venue can comfortably seat up to 500 guests with fully accessible facilities including large handicap restrooms and climate control for year-round comfort so everyone can focus on celebrating your special day.

What Are Maryland's Best Venues for Remote Participation?

Chesapeake Bay Beach Club provides stunning waterfront settings that enhance the virtual experience for guests who can't attend in person. You'll love their post-event storytelling approach that keeps remote guests feeling connected. Graduate Annapolis gives you advanced tech infrastructure for high-quality streaming with nautical-themed digital backdrops that help engage virtual viewers and make them feel part of your celebration.

Which Maryland Venues Feature Outstanding Culinary Experiences?

Valley Country Club set in a grand 1850s mansion offers all-inclusive packages with elegant butlered hors d'oeuvres and complete meal service that impresses even the most discerning guests. Their crab cakes are simply phenomenal and often receive rave reviews from attendees long after the event. You'll benefit from their over 70 years of hosting expertise that ensures everything from appetizers to dessert flows seamlessly.

What types of wedding venues are in Little Orleans, MD?

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