Beachfront vacation rentals in Talbot County

Private Waterfront Cottage on Bolingbroke Creek

Totally Private, quiet water-front cottage with wood-burning fireplace and exclusively private 60' Lap Pool (open mid-April to mid-October), large open Pool House and Pier. The nearest residences in the area are far removed from this cottage for a great feeling of seclusion and privacy for the cottage, pool, lawns, and gardens; all for the exclusive use of the cottage guests. Located between the beautiful villages of Easton and Cambridge -- close to Trappe, Oxford, and St. Michaels. STN-22-17

Cottage #1 Lighthouse First Cottage down driveway

OPEN March 25th until October 31st each year. No 1 is First cottage down drive has a full Kitchen, dining table, queen size bed in one open room. Full size Futon, Please call Jaimie upon arrival. Check in 3pm Check out 11am promptly please. Sorry No pets allowed! Bring: bed linens, Towel set, Coffee, filters and condiments for standard pot, bottle waters we are on a well safe to cook with. Boats are separate rentals 16’ , 9hp motor full day $250. 14’ Ft Boat rental with motor 9hp $225 full day

Private Beach Front Marina House

Beautiful waterfront property with private beach shared with one other family, ideal for family gatherings, located within walking distance of Kent Point Marina and convenience store. Enjoy a relaxing evening with family and friends sitting on the outdoor patio overlooking the Chesapeake Bay. You will have exclusive views of fresh-caught crabs & fish as they come off the boats during Summer. If you enjoy crabbing, fishing, boating, kayaking, swimming - it can all be done from this property.

Cottage on the Bay

Escape to this beautiful cottage overlooking the Chesapeake Bay. Just steps from the beach, this getaway offers water views right from the comfort of the living room. The interior has been remodeled and stylishly furnished, with two bedrooms and one bathroom. This cottage is perfect for couples, small families, or a peaceful solo retreat. Minutes from Downtown Annapolis, the Naval Academy, and other points of interest. NOTE: currently doing yard work; the backyard does not have grass yet

Heide's GuestHouse

Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambridge. Visit the Harriet Tubman Museum, dine on fresh local seafood, or enjoy a leisurely stroll along the Choptank River — all just steps from your front door. Back home, rest and relax on the shared patio, or curled up in front of the TV. Traveling with a pet, or maybe a larger crew? Make use of this vacation rental's pet-friendly policy and additional rental home on-site.

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

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Two inflatable paddleboards, one inflatable kayak and one inflatable 2 seater kayak available for use. Limited size life jackets available.

Cottage at Goose Neck Point

Romantic one bedroom, one bathroom waterfront cottage with direct access to the Tred Avon River. Beautifully renovated interior. Spacious living areas and kitchen. Gorgeous water views from all rooms. Home features a screen porch and sun porch. It’s a short drive from restaurants, local shops, specialty stores and farmers market. Just minutes from Easton and St. Michael’s. Bikes, paddle board, and kayaks are available for guest use. 3 night minimum stay Talbot Co. STR#ST-261-HAR

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House – 1,800 sq ft. Chesapeake Bay views. Across from Kentmorr Beach Bar & Grill, Marina & charters, and minutes to Matapeake Beach. Perfect for holidays, wedding accommodations, small family gatherings, fishing trips, or golf getaways. Features 4 bedrooms/3 baths (4th is a large family room with smart TVs & fireplace), kitchen, open dining/living, spacious deck, huge yard, and your own private beach volleyball court.

Ferry Bridge House

Located on a private peninsula surrounded by the Miles River, Ferry Bridge House is a hidden gem that feels a world away. This tranquil, two acre property is secluded but the conveniences of Easton and Saint Michaels are just few minutes away. There are gorgeous water views from every room in the house and lots of space for you to relax and unwind. (STRN-24-18). Ferry Bridge House. A very good place to be.