Holiday rentals with lake access in Talbot County

Charming Studio in the heart of St. Michael's, MD.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Chesapeake Bay The Perfect Waterfront Escape!

*NEW In-ground Large private pool! A private oasis. This exceptional 5 bedroom, 6 bathroom Rural waterfront Eastern Shore home sits on over 7 acres and boast endless water activities, including kayaking, crabbing or fishing. You can drift off to sleep in the oversized main suite with a perfect waterfront view! Enjoy the Eastern Shore lifestyle in this beautiful backyard complete with a mesmerizing water garden and firepit. Crab or fish from the shoreline for dinner or take in an amazing sunset!

• Peaceful Point • A relaxing waterfront retreat

Welcome to Peaceful Point! Come enjoy the beauty of the water and the serenity it brings at Peaceful Point. This brand new remodel is fresh on the market with 3 bedrooms, 2 bathrooms, and custom great room with vast views of the Choptank River from every seat. Enjoy the screened in porch over looking the cove, a vast yard, deck and pier to crab and fish, as well as kayak and paddle board. Privately located yet only 20 minutes from restaurants + shopping. Come relax with the family at PP!

Tilghman Retreat: A house on the Chesapeake Bay.

License: STRN-23-41 An amazing escape on the Chesapeake Bay. Explore Tilghman Island by bike or boat. Enjoy fresh seafood from the local seafood market or catch something fresh from the pier. The house includes access to the private pier, large backyard, fire pit, grill, 2 person canoe, 2 stand-up paddle boards, and bikes. This is a unique spot with beautiful sunsets. Enjoy local restaurants on the island. Close to St. Michaels (15 miles) with boutique shopping and excellent dining options.

3Br/1Ba Pondview Longsdale House

Experience the charm of historic Easton at The Pondview Langsdale House—a restored 1300-sq-ft, 3BR/1BA retreat with a private balcony and pond views. This upper-level apartment features modern comforts while honoring its 19th-century roots. Experience all this while being within walking distance from downtown Easton's major attractions. Your stay supports Halo's Haven Rescue, as hosts use proceeds to save animals in need. Enjoy downtown's attractions or simply relax with serene pond views.

Waterfront Modern Guest Barn

Find peace and reconnect with nature at this award winning guest barn. With its simple geometry and bucolic setting overlooking a quiet river of the Eastern Shore, this gem at the edge of a farm field could easily be mistaken for a working barn. But when you slide open the pair of two-story barn doors, you find a beautiful modern guesthouse full of light from the wall of windows facing the river. The setting is incredibly peaceful, and is a wonderful romantic escape or family getaway.

Panoramic water views

Tilghman Island Point of View. Our Island is perfectly situated on the Maryland crab and oyster trail. Step back in time to a slower lifestyle and observe the waterman’s way of life. Enjoy our two-bedroom coastal cottage and Island attractions. Enjoy the bird’s eye view of the local waterman in and out of the harbor seeking the days catch. Walk or kayak the shoreline. Take a stroll or ride a bike to Island attractions including all restaurants and shops. Arrive by boat or car.

Saint Michaels Waterfront Home

This beautiful waterfront home sits just over the bridge entering St. Michaels. Two large bedrooms, two full bathrooms, and Two sofas make this a very spacious for a large amount of guests. 1 minute to St. Michaels, 7 minutes to Easton and 30 seconds (right around the corner) to The Oaks Wedding Resort. Lots to do including kayaking, paddle boarding, biking or just taking in the views and wildlife. Great restaurants and local shops within minutes from this house! ST-739-YOS

The Cottage at Broad Creek

Your Private Waterfront Escape on Maryland's Eastern Shore Wake up to panoramic water views from your soaking tub. Kayak from the private dock, cook your catch in the chef's kitchen, then gather at your waterside fire pit as the sun sets over the bay. Minutes from historic St. Michaels yet secluded enough to feel like your own sanctuary. Perfect for couples seeking both adventure and relaxation, whether celebrating a milestone or simply unplugging together.

Charming cottage, FP, 1 blk water, historic area

A peaceful oasis near the water in the center of Cambridge. Tucked away at the end of a cul-de-sac with historic connections, this private, charming antique-filled cottage is steps away from the river. Enjoy three comfortable bedrooms all with en-suite bathrooms, and 2 living areas w/ fireplace and view of the Choptank River, with plenty of room for family and friends to entertain. Close to all amenities, Gerry Boyle Park and the waterfront.