Vacation rentals with a patio in Talbot County

Cozy Guest House Near Park

This lovely guest house is located in the historic district of Cambridge within 3 blocks to the Great Marsh/Gerry Boyle waterfront park. This cozy space includes a full kitchen with dishes, living space with reclining sofa, new Bedstory medium firm bed separated by an antique armoire as well as a large bathroom. You will have a private parking area and separate entryway through a private courtyard. Less than 1 mile to historic Cambridge. Near the start of annual races and waterfront activities.

Little Slice of Cambridge. 2 bedroom, pet friendly

You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

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.

Loon Cottage on Leeds Creek

Loon Cottage is a place where you can get away, put your phones down, take long walks in the woods, read on the patio, canoe on the river, cook big meals, and spend time with your favorite people. It’s cozy, comfortable, and just a little bit nostalgic. Decamp from the City to work remotely for a few days. Bring the family out to change the scenery on your weekend routine. Pack friends into the car for some low key shenanigans. Or some combination of all the above. Follow along @loon_cottage

Waterfront Home & POOL near St. Michaels & Easton!

Beautiful WATERFRONT 4 bedroom/4 bath home with a large 3.5 acre yard and private in-ground POOL, dock, fire pit & kayaks! Our family recently purchased and remodeled the entire home. Everything is new! The home is located minutes between Easton and St Michaels. Each bedroom is very spacious and 3 of the bedrooms have King beds. The "kids" room has a Queen over Queen bunk bed and another queen bed. There is a separate TV and rec room for kids too! STRN 23-54 (Talbot County license number)

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Shipwrights Cottage in Town!

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Waterfront Farmhouse Meets Modern Luxury

Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

Charming House, Quiet Neighborhood (Entire House)

This beautiful house has it all: the charm of a 1960s brick ranch with a fully updated interior. All new flooring, new appliances, and new furniture create a fresh, clean feel. The Chesapeake Bay is in view across the street and the full acre backyard offers a quiet, peaceful view of nature. The outdoor dining table and love seat provide the perfect setting for a peaceful visit. This property is 5 minutes from downtown Easton, 15 minutes from St. Michael's. License #STN 22-23.