Beachfront vacation rentals in Talbot County

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Top-rated beachfront rentals in Talbot County

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Guest favorite

Apartment in Cambridge

4.92 out of 5 average rating, 101 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”.

Jun 24 – Jul 1

ﺩ.ﺇ542 per night

Guest favorite

Guest suite in Cambridge

4.96 out of 5 average rating, 267 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 !

Oct 28 – Nov 4

ﺩ.ﺇ554 per night

Guest favorite

Home in St Michaels

4.85 out of 5 average rating, 107 reviews

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Feb 7 – 14

ﺩ.ﺇ1,257 per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 12 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.

Oct 17 – 24

ﺩ.ﺇ1,533 per night

Guest favorite

Home in Oxford

4.96 out of 5 average rating, 184 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.

Jan 2 – 9

ﺩ.ﺇ1,100 per night

Superhost

Home in Queenstown

4.81 out of 5 average rating, 143 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.

Nov 15 – 22

ﺩ.ﺇ3,398 per night

Guest favorite

Home in Cambridge

4.95 out of 5 average rating, 100 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.

Oct 13 – 20

ﺩ.ﺇ948 per night

Superhost

Cottage in Neavitt

4.69 out of 5 average rating, 16 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.

Nov 2 – 9

ﺩ.ﺇ472 per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 50 reviews

Osprey's Retreat - Waterfront with private beach!

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.

Sep 30 – Oct 5

ﺩ.ﺇ1,608 per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Aug 26 – Sep 2

ﺩ.ﺇ542 per night

Guest favorite

Home in Cambridge

5.0 out of 5 average rating, 6 reviews

Magical Waterfront Home-Dock, Firepit, family fun!

Heron's Rest is a stunning home w/ magnificent water views, expansive patio, fire pit and dock - a peaceful place to gather with family and friends. Incredible location to explore the stunning and historic Eastern Shore and Historic Cambridge. Easy drive to the Atlantic beaches--you CAN have it all- boat, kayak, fish, birdwatch, explore Blackwater Wildlife Refuge, Easton, St. Michael's. There is a 3-night minimum from May 24 - Sept 02.

Dec 15 – 22

ﺩ.ﺇ2,497 per night

Guest favorite

Cottage in Oxford

4.96 out of 5 average rating, 68 reviews

Tilghman Cottage I - Cheerful and Charming Oxford

Cottage 1 is a sweet little Eastern Shore style bungalow with 1bd, queen - 1ba, Livingroom, kitchen, big screened in porch, off street parking, and private yard. Tilghman Cottages are located in the heart of beautiful Oxford Md. The area is ideal for cycling, kayaking, restaurants, bars. Charming towns close by to travel to and so much more. Come enjoy this tranquil little getaway today.

Feb 21 – 28

ﺩ.ﺇ1,075 per night