The Best All-Inclusive Wedding Venues in Chestertown, MD

The Best All-Inclusive Wedding Venues in Chestertown, MD

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3 Wedding Venues in Chestertown, MD

All-inclusive
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Celebrations at the Bay 

4.9

  • Up to 400 guests
  • All-inclusive
  • Indoor & outdoor

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.

Why you'll love this venue

  • Offers full-service amenities
  • Has a dance floor to dance the night away
  • Space for a large guest list

Venue considerations

  • Not for you if you are looking for something nontraditional
  • No free parking
  • No on-site guest accommodations
“We had our wedding in the ballroom. Very scenic and beautiful venue! Overall a pretty good venue that includes food, tables, chairs, linens, etc. The ballroom house itself is beautiful with lots of light indoors due to the large windows, and a nice deck for an outside ceremony. Zoe communicated with us and answered all our questions and did our tasting and planning, until a week before the actual day where we were assigned a day of coordinator. I found this system to be not great, since the day of coordinator was essentially a stranger that you've never talked to at all, and you basically have to re explain everything you want. Even though they have an online planning tool (which is old and outdated), I found that they got our aisle directions wrong, the reception layout wrong, and our dinner meals were wrong. Thankfully, we had a separate planner that was able to correct these things, so I recommend getting an outside coordinator that works directly with you if you have room in the budget. Another thing was our limited setup time of 1.5 hours meaning the florist and other vendors couldn't set up earlier with more elaborate decorations and had to do something simple. I found out that this is because they had another wedding at the same place before ours (literally ending at 4) and so they rush to get the place cleaned for the evening wedding. The main room and the suit was renovated, but the bathrooms were all still dingy and not the best/cleanest to use. The food was good though, better than we had at our tasting and they got it out fast. Our vendors were fed the same food, and our guests thought it was pretty good wedding food. Apart from the couple hiccups we had, we thought the venue was great overall and really beautiful and we don't regret having our wedding there at all. It could be a little bit better in the small details for the price though.”
Wendy G., a year ago
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Deep Blue at Kitty Knight 
Galena, MD
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $8,250

Our historic establishment is dedicated to providing an exquisite setting for all wedding-related occasions, including showers, welcome parties, rehearsal dinners, and more. Whether you envision an indoor affair accommodating up to 125 guests or an enchanting outdoor celebration for 150+ guests, both options offer stunning views of the Sassafras River. Our dedicated team is committed to ensuring that every detail of your event is flawlessly executed. We offer our guests a comprehensive wedding package, which can be further tailored to meet the unique requirements of their special day. From menus to personalized touches, we strive to exceed expectations and create unforgettable memories for you and your loved ones. To add to the historical experience, our 18th-century historic Kitty Knight Inn is located on the property and is available for guests to stay in. The inn has 11 recently updated rooms but still keep their historic charm that we are so well known for.

Why you'll love this venue

  • All-inclusive venue packages
  • Caters to out-of-town guests
  • Provides setup and cleanup

Venue considerations

  • Does not allow pets
  • Large venue, not ideal for small guest lists
  • On-site parking not available
Quick responder
Anchor Inn 

5.0

  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

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!

Why you'll love this venue

  • Designed for grand celebrations
  • Pets can join the celebration
  • Provides catering services

Venue considerations

  • Not wheelchair accessible
  • Large venue, not ideal for small guest lists
  • On-site parking not available
“The team at Anchor Inn was quick, easy, and friendly to work with throughout the planning process. The quality of their work was absolutely beautiful, stunning, and elegant. The food they served was amazing, and their day-of coordinator was everything we could have asked for. We couldn't be happier with how our special day turned out at Anchor Inn. They truly helped make our wedding day perfect in every way.”
Carolynn M., 3 months ago

Location flexible? Discover venues near Chestertown, MD

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The Estate at White Hall Vineyard

5.0 (11)

King George, VA
Farm 1750

5.0 (2)

Hustle, VA
New Kent Winery Vineyard Estate

2.0 (1)

New Kent, VA
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The Lewes Room at Irish Eyes

5.0 (2)

Lewes, DE
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King Cole Farm

5.0 (1)

Dover, DE
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Sunnybrae Mansion
Milford, DE
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Bayside Resort & Golf Club

5.0 (5)

Selbyville, DE
Atlantic Sands Hotel & Conference Center
Rehoboth Beach, DE
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Baywood Weddings

5.0 (7)

Millsboro, DE
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The Historic Cobalt Manor

5.0 (2)

Smyrna, DE
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Monroe Bay Winery, Wedding on the Water
Colonial Beach, VA
Good Luck Cellars

5.0 (1)

Kilmarnock, VA

Get inspired by real weddings in Chestertown, MD

View all real weddings in Chestertown, MD
Traditional Waterfront Wedding at Celebrations at the Bay
Minimalist Wedding at Level a Small Plates Lounge
Outdoor Summer Wedding at Mount Harmon Plantation
Tented Summer Soirée by the Coast
Classic Golfcourse Wedding
Backyard Wedding in Dover
Intimate Garden Wedding at Paca House And Garden
Personalized, DIY Wedding in Annapolis
Rustic Chic Wedding at the Bohemia Overlook
Rustic Outdoor Wedding
Outdoor Swan Harbor Wedding in Spring
Floral-Filled Library Romance Styled Shoot

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