Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings

Discover Watermark, a breathtaking 6,500 sq. ft. waterfront estate offering unparalleled views across 12 miles of the Chesapeake Bay. With spacious, light-filled interiors, four luxury master suites, a heated pool, and direct shoreline access, this extraordinary home is designed for relaxation, connection, and unforgettable memories.

We welcome guests to book for week-long to multi-week events retreats and private events such as:

✔ Family Gatherings & Multi-Generational Celebrations
✔ Weddings (On-Site Tent and Parking Space Available) & Rehearsal Dinners (Off-Site Ceremonies Welcome!)
✔ Corporate Retreats & Creative Workshops
✔ Wellness, Yoga & Inspiration Retreats
✔ Exclusive Photo & Film Shoots

We do not offer short-term vacation rental stays at this time and are only event based. Long-term rentals are a minimum of 13 weeks at special discount rates.

- Prime Location – Just 6 miles from the charming shops, restaurants, and attractions of St. Michaels and Tilghman Island.

Inside Watermark
Luxury Accommodations with Unforgettable Views
-Four Grand Master Suites – Each with a king-size bed, luxury linens, a private spa-style bathroom, and stunning water views. Suites also include a daybed and trundle, providing flexible sleeping arrangements.
- Wheelchair Accessible – First-floor access with no barriers.

Spacious Living Areas & Gourmet Kitchen
- Fully Equipped Chef’s Kitchen – Featuring a professional AGA stove and oversized island.
- Floor-to-Ceiling Bay Views – A wall of glass invites natural light and breathtaking scenery.
- Cozy Evenings – Enjoy the 75” & 84” 4K TVs, game room, bar area, and indoor fireplace.

Unplug, Recharge & Explore
- Heated Pool – Open April to October (weather-dependent).
- Private Beach & Dock – Swim, kayak, or crab at low tide (beach tide dependent)
- Outdoor Fire Pit & BBQ – Perfect for al fresco dining and evening gatherings.
- Incredible Wildlife Viewing – Spot bald eagles, herons, and osprey.

Exclusive Experiences at Watermark
- Scenic Bike Rides – Ride along the dedicated paths of Tilghman Island Road.
- Kayaking & Watersports – Five kayaks provided to explore the open bay.
- Crabbing at Low Tide – Simply wade in and see if you can net fresh Chesapeake blue crabs like the pros out there!

Plan Your Stay
- Available Year-Round – Enjoy seasonal specials with reduced rates through Memorial Day!
- Dog-Friendly – Up to 2 pets welcome ($100 per pet).
- High-Speed Internet – Perfect for remote work and extended getaways.

- Book Early – 2025 Availability is now Available!
- Experience the magic of Watermark – where relaxing meets nature on the Chesapeake Bay.

Note:
Watermark is not a short-term rental at this time. However, we welcome week to multi-week event stays and private events. We are an ideal home base for wedding guests, extended corporate groups, and special celebrations in the St. Michaels area.