The Best Beach & Waterfront Wedding Venues in Chestertown, MD

The Best Beach & Waterfront Wedding Venues in Chestertown, MD

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5 Wedding Venues in Chestertown, MD

Beaches, waterfront settings
Quick responder
The Anchorage1800 

5.0

Trappe, MD
  • Up to 100 guests
  • Raw space
  • Outdoor
  • Starts at $5,000

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.

Why you'll love this venue

  • Provides a dedicated team on-site
  • Caters to out-of-town guests
  • Surrounded by nature

Venue considerations

  • Not wheelchair accessible
  • Does not have a dance floor
  • Couple must handle cleanup and setup
The Anchorage was amazing! My wife and I got married here last June, and to say everything was perfect would be an understatement. It's hard to put into words explaining how great Woody and Michelle were helping us make our special day go exactly as planned. The property is beautiful, spacious, and well kept. The waterfront view was the perfect backdrop for our ceremony (Woody even went out of his way to make an aisle of sand for us to walk down). The cigar shack was awesome and the barn was also set up for me and my groomsmen to get ready and hang out until the big moment (they especially enjoyed the darts, ring and hook, and bar with a kegerator). My family and I were very happy with the rooms which were spotless, comfortable, and included refrigerators/kitchenettes. My wife was very happy with her space to get ready, especially with Michelle doing everything she could ensuring the girls had what they needed and making sure everyone was stress free! Woody and Michelle were more than accommodating. Breakfast was always delicious (the smoothies and Woodys Waffles were my favorites). They were also life savers dealing with our vendors dropping stuff off (at times earlier than expected), even using their golf cart to help move stuff down to the beach to help set up. The golf cart also came in handy taxing people up and down the hill when needed! I HIGHLY recommend this venue! Woody and Michelle are two of the most kind, accommodating (and hilarious) people I've ever met, and I can't begin to thank them enough for everything they did to make sure our special day went off without a hitch. We fully intend on coming back to enjoy their beautiful BnB again!
Daniel N., 7 months ago
Quick responder
Drumore Mill 

5.0

  • Up to 125 guests
  • Select services
  • Outdoor
  • Starts at $4,700

Drumore Mill is a different world. It is nestled in a corner of the most rustic township in Amish Lancaster County, Pennsylvania. The mill was built in 1752 as a sawmill and a grist mill. It sits in a hollow with 30 acres of tall cliffs and old trees to provide privacy, warmth, and natural beauties. There is a pristine creek that meanders through the property. The Fishing Creek supports native trout and other rare small fishes. The waterfall is adjacent to the buildings. There is a hiking trail within the property. There is wetland and much more. The combination of rustic setting, natural beauties, and historical features makes Drumore Mill amazingly beautiful. One has to see it to believe it.

Why you'll love this venue

  • Venue is completely outdoors
  • Provides setup and cleanup
  • Has a glamorous vibe

Venue considerations

  • Does not allow pets
  • Not for you if you're looking for a sleek and contemporary space
  • Additional event staff required
Awarded Best of Zola
Drumore Mill was an absolutely stunning venue to use for our special day (really weekend). We loved the ease of booking the venue, touring with Thuy, and the promptness and flexibility they offer. An added bonus is the available on site lodging for rental, which we made great use of for our close friends, family, and wedding party to stay in the night before and night of the wedding. We enjoyed the Great Room in the Grist Mill for our rehearsal dinner. Our guests loved how spacious Drumore Mill was, and we appreciated all the attention to detail such as included (but still optional) decor and greenery, and the setup of chairs and other items for the ceremony space. Being able to bring in all of our own vendors at no additional cost was fantastic. The value for renting the property from Thursday to Saturday morning was unmatched and completely worth it. We would recommend Drumore Mill to anyone, and we look forward to booking the property in the future for non-wedding related stays with friends and family.
Maureen B., a year ago
Quick responder
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
Brittland Manor/ River Lodge 
Chestertown, MD
  • Up to 400 guests
  • Raw space
  • Outdoor
  • Starts at $45,000

Historic mansion, river vistas and forever fields, the world of Brittland personifies an old world luxury elegance in a rural setting. The hilltop setting commands magnificent views of the Chester River. Brittland Manor gives the discerning couple a series of settings and moods to create their distinctive celebration. This secluded mansion has a garden, pool, wildlife pond, 530 riverside acres, and woodside fields. A waterfront cottage perfectly compliments the 530 acre Brittland Manor estate. It offers a rustic riverside setting for ceremony and/or a rehearsal dinner.

Why you'll love this venue

  • Wheelchair accessible
  • Rustic yet refined style
  • Surrounded by nature

Venue considerations

  • Does not allow pets
  • No venue-provided food services
  • Does not have a dance floor

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