Beachfront holiday rentals in Talbot County

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Top-rated beachfront rentals in Talbot County

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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

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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

Guest favourite

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.

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Campervan/Motorhome 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

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Home in Stevensville

4.96 out of 5 average rating, 52 reviews

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House: almost 1800 sq ft. Incredible Water View home across from Kentmorr Beach Bar & Grill/Marina/Fishing Boats near Matapeake State Park & Beach. Perfect for holidays, birthdays, wedding guests, team builds, family fun, fishing, golfing, etc. 4 Bedrooms, 3 Full Baths, 4th Bedroom is large family room with big Internet TVs/fireplace plus a Kitchen, Living/Dining Area, and a huge yard with your very own private beach volleyball court and spacious deck overlooking the Chesapeake Bay.

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Hotel room in Oxford

4.96 out of 5 average rating, 134 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 favourite

Home in Stevensville

4.89 out of 5 average rating, 54 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

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Home in Stevensville

4.88 out of 5 average rating, 16 reviews

Waterfront Escape with Pool Nature Lover Paradise

Discover the perfect blend of relaxation and adventure at our stunning waterfront home. With breathtaking water views, a private swimming pool, and plenty of space to unwind, this is the ultimate retreat for families, groups, or anyone seeking a serene getaway. Swin, fish, crab or paddle right from our private beach, cooling off in the pool, or simply soaking in the peaceful surroundings, or take in the sight of wildlife, including bald eagles, blue herons, ospreys, swans, ducks, and more

Guest favourite

Home in Stevensville

4.95 out of 5 average rating, 97 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.

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Guest house in Cambridge

4.95 out of 5 average rating, 22 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.

Home in Annapolis

4.94 out of 5 average rating, 33 reviews

Waterfront Home - Amazing Views - Beach Adjacent

WATERFRONT with Amazing Views!!! Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New modern well-equipped kitchen, open deck with gas grill, front porch with a 180 degree unobstructed view of the bay, new beds, walk to a private beach, evening campfires allowed on the Bay Ridge beaches, beach gear included. We are in the process of updating the furnishings throughout, will be newly decorated as of March 1, 2025. New photos in March.

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Guest house 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