Beachfront vacation rentals in Talbot County

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Top-rated beachfront rentals in Talbot County

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A charming two-story cottage is surrounded by lush greenery and shrubs. The exterior features white siding, green shutters, and a brick chimney. A welcoming porch with steps leads to the front door, providing access to the tranquil surroundings.

Cottage in Trappe

4.87 out of 5 average rating, 30 reviews

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

Superhost

A charming cottage exterior is presented, featuring light-colored siding and a vibrant red door. Two teal Adirondack chairs are positioned on a grassy area, offering a cozy spot to relax. Lush greenery and small shrubs frame the entrance, enhancing the inviting appearance.

Cottage in Saint Michaels

4.79 out of 5 average rating, 29 reviews

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

Top guest favorite

An outdoor patio area is featured with comfortable seating options facing a lush green lawn. In the distance, the serene waterfront can be seen, framed by trees. The space offers a peaceful environment for relaxation and social gatherings.

Home in Stevensville

5 out of 5 average rating, 15 reviews

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.

Top guest favorite

A stationary RV is positioned on a grassy area overlooking the Chesapeake Bay, bathed in warm sunset hues. Two chairs and a small table are placed nearby, enhancing the outdoor space. The tranquil bay and distant boats are visible, creating a serene environment.

Camper/RV in Stevensville

5 out of 5 average rating, 9 reviews

Charming RV With A Water View

Indulge in a waterfront paradise in our inviting stationary RV rental on the Chesapeake Bay. Sleeps 2 adults + 2 children with a queen bed + queen sleeper sofa. Positioned on the bay for easy water access and breathtaking sunset views. Enjoy the shared use of a heated pool, grill and pier. Experience swimming, fishing, crabbing and outdoor fun right at your RV "home." Close to wedding venues, marinas, charter fishing, dining spots, golf courses, parks, and biking trails and Annapolis and D.C

Guest favorite

The living room showcases large windows that provide ample natural light and offer views of the surrounding area. A comfortable blue velvet sofa is paired with two light-colored armchairs and a wooden coffee table, creating a welcoming seating arrangement on a light-colored area rug.

Home in Annapolis

5 out of 5 average rating, 5 reviews

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

Top guest favorite

A charming boutique hotel is surrounded by lush, manicured lawns and vibrant autumn foliage. The tranquil waterfront is visible in the background, with a gently sloping area leading down to the water's edge. A clear sky enhances the peaceful atmosphere of the outdoor setting.

Hotel room in Oxford

4.97 out of 5 average rating, 146 reviews

Water View with Beach, Walk to restaurants & shops

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning waterfront views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored water view rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.

Guest favorite

A sandy beach is shown along the shoreline, bordered by tall grasses and scattered vegetation. The view extends towards a two-story house positioned in the background, with soft clouds and a blue sky adding to the serene coastal atmosphere.

Home in Stevensville

4.9 out of 5 average rating, 60 reviews

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

Guest favorite

A wooden deck area is highlighted with four Adirondack chairs arranged around a central fire table, where flames flicker gently. Beyond the deck, a well-maintained lawn leads to the bay, visible in the distance under a colorful sunset sky.

Home in Stevensville

4.95 out of 5 average rating, 99 reviews

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.

Top guest favorite

A view of a white two-story house with a screened porch, situated near a sandy area and a dock on the water. Alongside, manicured lawns and trees frame the property while the calm water reflects the surroundings, creating a serene outdoor space.

Guesthouse in Cambridge

4.96 out of 5 average rating, 24 reviews

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.

Top guest favorite

A charming waterfront cottage is viewed from an expansive green lawn. The white exterior is adorned with dark shutters, and a smoke-colored roof complements the brick chimney. Lush greenery and blooming flowers frame the entrance, enhancing the serene landscape surrounding the home.

Guesthouse in Royal Oak

5 out of 5 average rating, 14 reviews

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

Top guest favorite

A wooden dock extends over calm waters, leading towards a charming two-story house surrounded by trees. The sandy beach area is visible, along with several white adirondack chairs arranged under the shade. The house, featuring large windows, sits just beyond the beach.

Home in Cambridge

4.96 out of 5 average rating, 93 reviews

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.

Top guest favorite

Home in Stevensville

4.96 out of 5 average rating, 53 reviews

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.