Beachfront vacation rentals in Talbot County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Talbot County

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Rental unit in Cambridge

4.92 out of 5 average rating, 118 reviews

Little Slice of Cambridge. Newly listed, 2 bedroom

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”.

Guest favorite

Home in Chester

5 out of 5 average rating, 31 reviews

*Waterfront Sunset Bayview* sleeps 6

Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent direct sunset views, that force you to stop and take it in! Our open-concept home is tastefully decorated with a blend of modern amenities and cozy charm, complete with large windows that allow natural light to fill the space along with stunning views of the Bay. Escape the hustle of everyday life and immerse yourself in the serene beauty from the comfort of your private retreat.

Guest favorite

Guest suite in Cambridge

4.96 out of 5 average rating, 291 reviews

Oakley Suite

5 minute walk to restaurants and shops, 3 min.to the water. Ideal setting with lovely rear patio and garden with entrance to private family room. Stairs to upper level with 2 very large and private guest rooms. Landing at top of steps presents a convenience station with Keurig, microwave, and mini fridge. This Suite is completely private and includes 2 bedrooms, bath, family room, convenience station, and rear patio, all for one price! 1st floor Owners Suite available as well for a total of 8 !

Superhost

Home in Saint Michaels

4.75 out of 5 average rating, 84 reviews

In Town St. Michaels Waterview Cottage

The magical John Bruff house is a beautifully restored 2 bedroom historic house sitting on the St Michaels harbor and Town park, with amazing water views from every room. It is a short walk to parks, museums, shops, restaurants, Town pool, tennis courts, library - almost everything in Town! Perfectly suited for a small family, 2 couples, or a romantic getaway. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are "last minute" bookings.

Guest favorite

Home in Oxford

4.96 out of 5 average rating, 202 reviews

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Superhost

Home in Queenstown

4.81 out of 5 average rating, 155 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Guest favorite

Rental unit in Cambridge

4.95 out of 5 average rating, 21 reviews

Happy Campers Waterfront Suite

Come and experience a relaxing getaway at our Waterfront Suite! Happy Campers is located near the corner of the Choptank River and the Chesapeake Bay, surrounded by acres of farm land. You will enjoy quiet days, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery. A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park.

Guest favorite

Home in Stevensville

4.91 out of 5 average rating, 35 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

Home in Cambridge

4.94 out of 5 average rating, 119 reviews

Peaceful Historic House Near Water, with Hot Tub!

Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Guest favorite

Home in Tilghman Island

5 out of 5 average rating, 10 reviews

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.

Guest favorite

Cottage in Neavitt

4.72 out of 5 average rating, 18 reviews

Grandview - Cottage 1A, King Bed, Pool, Bay, WIFI

Charming cottage on the water. Furnished with a king sized mattress, full kitchen, refrigerator with ice maker, microwave, gas stove and oven, shower, screened and glassed in porch, fireplace, WIFi, TV, Air Conditioning, grill, 2 piers, and pool access. 1A. There is a cleaning fee per cottage. It is based on Daily and weekly rates per cottage. Cottages 1 A is $15.00 a night or $45 for the week. Linens are available for $15.00 per person through the owner or bring your own.

Guest favorite

Home in Cambridge

5 out of 5 average rating, 108 reviews

The Magnolia Cottage. Historic District Charmer

Welcome to our beautifully restored Queen Anne Victorian with new Mid-century modern interior furnishings . While this house is perfect for a family up to 6 we also understand that there are maybe just 1 or 2 guests that would like to stay as well. For this reason we are offering a discount when only 1-2 guests stay with us and take advantage of the first floor bed/bath only. We will deduct $50 off of the cleaning fee after checkout!