In this The Oaks Wedding Venue Spotlight, we’ll explore the property’s immaculate service, the charm of St. Michaels, and the exquisite ceremony and reception spaces available for your celebration. We’ll also highlight the exceptional amenities that make this venue so special, from sunset sailing excursions to garden cocktail hours. Whether you’re envisioning an intimate waterfront ceremony or a grand tented reception, the The Oaks offers an unforgettable backdrop for your wedding day.
Nestled along a serene cove off the Chesapeake Bay, The Oaks Waterfront Inn offers a harmonious blend of historic charm and modern luxury. Located just minutes from the quaint town of St. Michaels, Maryland, this boutique hotel provides an idyllic retreat for those seeking tranquility and elegance on the Eastern Shore.
With its picturesque waterfront setting, The Oaks serves as a premier destination for weddings, corporate events, and leisurely escapes. The inn’s commitment to personalized service and attention to detail ensures that every guest experiences the warmth and hospitality that define this exceptional venue.
Welcome to The Oaks!
The Oaks stands out for its unique combination of seclusion and accessibility. Set on 10 acres of beautifully landscaped grounds, the property offers expansive views of Oak Creek, providing a serene backdrop for relaxation and celebration. The inn features fourteen well-appointed guest rooms and a private bridal cottage, each designed with comfort and elegance in mind.
Guests can enjoy a variety of on-site activities that embrace the natural beauty of the surroundings. Bicycles and canoes are available for those looking to explore the creek and nearby trails, while the outdoor pool offers a refreshing respite during warmer months. The inn’s inviting common areas, including a cozy lounge and waterfront deck, provide perfect spots for unwinding and taking in the tranquil views.
The Oaks Waterfront Inn Location & Travel
Reaching The Oaks Waterfront Inn is convenient for travelers from various locations. The inn is approximately a 90-minute drive from both Baltimore and Washington, D.C., making it an accessible escape from urban centers. Additionally, for those preferring public transportation, train services to nearby towns are available, with car rentals or taxi services providing the final leg to the inn. Moreover, the scenic drive through Maryland’s Eastern Shore adds to the overall experience, setting the tone for a peaceful retreat.
For more details, you can contact the Inn at or visit their website.
The Oaks Waterfront Inn Address: 25876 Royal Oak Rd, Easton, MD 21601.
Phone Number for The Oaks Waterfront Inn: (410) 745-5053.
Staying On Site
Staying at The Oaks Waterfront Inn offers a cozy, boutique experience centered on relaxation, comfort, and scenic beauty. The inn features 14 individually decorated guest rooms, each with a unique layout and character. Moreover, many rooms offer views of Oak Creek, and several include private balconies, jetted tubs, or fireplaces for an added touch of luxury. The charming bridal cottage, located just steps from the inn, provides a private and serene retreat—perfect for wedding preparations or a quiet couple’s escape. Overall, all accommodations are designed with a focus on comfort and simplicity, blending the charm of a historic Eastern Shore estate with modern touches.
Guests are invited to enjoy a complimentary continental breakfast each morning, served in the welcoming dining area. During warmer months, the inn’s outdoor pool and surrounding lawn provide plenty of space to relax and unwind, while complimentary bicycles and canoes encourage exploration of the property and nearby trails. Whether enjoying a morning coffee on the waterfront dock or watching the sunset over the creek, a stay at The Oaks feels intentionally slow and delightfully serene, making it an ideal choice for both destination wedding guests and those simply looking for a peaceful Chesapeake Bay getaway.
Nearby, The Spa at Perry Cabin offers a variety of wellness programs, inspired by the beauty of the Eastern Shore, providing the perfect opportunity for relaxation.
The Oaks Wedding Venue Sites
The Oaks Waterfront Inn offers an enchanting setting for couples seeking a memorable wedding experience. The venue’s waterfront lawn serves as a serene backdrop for outdoor ceremonies, where couples can exchange vows with the tranquil waters of Oak Creek enhancing the romantic atmosphere.
For the reception, The Oaks features an elegant grand ballroom that comfortably seats up to 250 guests. This space is characterized by its classic design and offers a sophisticated ambiance for dining and dancing. Adjacent to the ballroom, the covered dock provides an exceptional setting for cocktail hour, allowing guests to enjoy panoramic waterfront views in a sheltered environment.
In the event of inclement weather, the covered dock can also serve as an alternative ceremony location, ensuring that the celebration proceeds seamlessly regardless of conditions.
Planning an Inn at Perry Cabin Wedding
Planning a wedding at The Oaks is a collaborative and personalized process. The venue’s dedicated team assists couples with vendor recommendations, timeline creation, and on-the-day coordination, ensuring a seamless experience. The inn offers exclusive use of the property for weddings, allowing for a private and immersive celebration. Accommodations for the wedding party and guests are available on-site, providing convenience and a shared experience for all attendees.
Here are a few tips inspired by my experience photographing weddings at The Inn at Perry Cabin:
- Create a schedule for your guests with a mix of activities and rest time. Think about providing structure while allowing room for relaxation. Keep in mind the variety of personalities you’ll have—some of your guests might be early risers, others late sleepers. Provide opportunities for both, such as an early bike ride to downtown Saint Michael’s for coffee and pastries and a late morning tennis tournament. One of the joys of an intimate wedding is making it a truly unique experience for you and your guests. Lean into that as you craft your itinerary.
- Consider the seasons. The Inn is beautiful year-round, but is your celebration in early fall, when guests might appreciate cozy throw blankets? If your wedding is in late spring or summer, you might want to provide fans, parasols, and a refreshing welcome drink to keep your guests comfortable during an outdoor ceremony. These little details make a big impact on your guests’ experience and comfort.
- Personalized details go a long way toward a luxurious experience. Have your stationer craft unique elements like room tags and welcome notes. These become keepsakes and infuse your wedding design into the weekend.
Things to Do Around The Oaks Waterfront Inn
Beyond The Oaks serene waterfront setting, St. Michaels offers a variety of activities and local treasures. Take a leisurely stroll through the historic streets. Stop by local favorites like Joyce’s Ice Cream, a beloved spot for handmade ice cream. Also, visit Blue Crab Coffee Co., known for its rich brews and cozy atmosphere. For those interested in local culture, the St. Michaels Museum offers fascinating exhibits on the town’s maritime history. Dining options include The Crab Claw, an iconic waterfront restaurant with fresh Maryland crab cakes. You can also enjoy farm-to-table dishes at Ava’s Pizzeria & Wine Bar. Outdoor enthusiasts will love the Chesapeake Bay Maritime Museum, which offers boat tours and exhibits. Nearby, Tilghman Island provides peaceful walking trails and stunning waterfront views.
The Oaks Wedding Cost
The cost of hosting a wedding at The Oaks Waterfront Inn varies based on factors such as the season, guest count, and specific event requirements. The venue offers tailored packages to suit different budgets and preferences. Prices typically start around $20,000-$30,000 but couples on average invest at least $80k-$100k in their Oaks Waterfront Inn Wedding. Additional costs include photography, planning, catering, floral design, rentals, stationary, and other personalized services to ensure a bespoke wedding experience. For a wedding that blends elegance with breathtaking natural beauty, The Oaks delivers an extraordinary experience.
For your Oaks Waterfront Inn wedding, plan for three days of activities. Start with curated welcome bags for your guests upon arrival. After settling in, enjoy the inn, explore the town, or visit the spa. Plan a coastal-themed welcome dinner with a locally sourced, farm-fresh menu, crisp white wines, and s’mores under the stars. The following day, hold your al fresco wedding ceremony on the waterfront lawn. That evening, enjoy a romantic reception filled with seasonal flowers, glowing candlelight, and endless celebration. On the last day, share a farewell brunch picnic on the croquet lawn as you reminisce and say your goodbyes.
I highly recommend working with an experienced wedding planner to coordinate events. I’m always happy to share planner recommendations who can craft enchanting celebrations. Here’s an example of a stunning event designed and produced by Stephanie of SRS Events that I photographed in 2024. Stephanie truly inspired everyone with her “Cottagecore on the Eastern Shore” caterpillar reception table design!
The Oaks Wedding Photography
The importance of capturing the beauty and emotion of your wedding day with artistry and authenticity cannot be overstated. As a film destination wedding photographer, my style complements the intimate, timeless, and romantic feel of The Oaks Waterfront Inn. Our heartfelt approach ensures we capture every moment with authenticity and intention. For more details on my destination wedding photography services, please visit my Experience page. please visit my Experience page.
I hope this post was as helpful as it was inspiring for your next journey to the Eastern Shore!
