House holiday rentals in Centreville

River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

Totally Renovated historic house near town center

19th century home. 55” TV in family room, 2 more. 1st floor primary with full bath. Hi speed internet. Pets welcome! Located in the historic district of Chestertown, 3 block walk from Wash College and the C'town waterfront. 2 primary bedroom suites (one on 2nd floor with king ) 2 bedrooms with queens. 100% cotton, 1000 thread count sheets and luxury mattresses. Loft connected to a 2nd story bedroom with queens Fenced yard, acre of gardens. Fire pit. New Weber grill

Cozy 3-bedroom home w/ Hot tub & firepit

This cozy, recently renovated home has the charm of days gone by. It is located with-in a 5 minute walk to the grounds of Washington College and a fifteen minute walk to Historic Downtown. There is an abundance of food and other conveniences close by. A perfect place to unwind and relax. A 20 minute drive to Rock Hall. Take in the beautiful Chester River and Chesapeake Bay area. Fishing, hiking and other outdoor activities to be enjoyed. Newly furnished rooms and fully stocked kitchen.

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Easton, Dover, D.C. and Baltimore. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

12 M to Naval Acadmey | Waterfront

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.

Pirates Perch

Rock Hall's most convenient vacation rental. Right on the parade route and walking distance to shops, ice cream, coffee, groceries and more! Sleeps 8 with 2 full baths. The master bedroom with full bath is on the 1st floor. Kitchen, dining room and living room. 3 TVs with WiFi internet. Off street parking for 3 full size vehicles.

Duchess of Kent: Walk to downtown & College

Location location location! We absolutely love the proximity of our house to campus, the historic district, and the river. Chestertown is charming and there are fun little shops and restaurants around every corner. Our home is cozy and perfect for entertaining. We hope you enjoy it as much as we do!