Venue photo 1

The Oaks Waterfront Inn

4.8(289)
Hotel

About

The Oaks Waterfront Inn offers a serene retreat on a secluded cove of Maryland’s Eastern Shore, blending spacious, well-appointed rooms and private cottages with stunning water views. Each accommodation features luxury baths, soaking tubs, and high-end amenities, complemented by a freshly prepared hot breakfast to start the day.

The venue’s renovated waterfront event spaces provide a tranquil, sophisticated setting for business meetings and small gatherings, with versatile indoor and outdoor areas designed for productivity and comfort. Conveniently located minutes from St. Michaels and Easton, The Oaks combines privacy with easy access to local business hubs, enhanced by attentive service and thoughtful touches like a complimentary shuttle service.

Best for

  • Executive retreats with private waterfront cottages
  • Client dinners in elegant on-site dining room
  • Multi-night group stays with personalized service

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

Waterfront Setting
Secluded cove with stunning water views
The venue is located on a peaceful, private waterfront cove on Maryland's Eastern Shore, offering event spaces and accommodations with epic water views and private balconies. This serene setting provides a distinctive backdrop for meetings and
Accommodations
Luxurious rooms and cottages with high-end amenities
Guests can choose from graciously appointed rooms in the main building or private cottages, all featuring king beds, soaking tubs, and upscale comforts like heated bathroom floors. The Waterfront Suite combines water views, private balcony, and
Food & Beverage
Gourmet dining with a waterfront view
The Oak Room restaurant offers a full menu with thoughtfully prepared, delicious meals and standout dishes like a top-rated huevos rancheros tostada. Guests enjoy cocktails crafted by skilled bartenders, complemented by a scenic deck for nightcaps.

At a glance

Rated 4.8 on Google · 289 reviews