Holiday rentals with beach access in Talbot County

4.91 out of 5 average rating, 129 reviews

Apartment in Cambridge

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”.

4.96 out of 5 average rating, 213 reviews

Home in Oxford

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.

5 out of 5 average rating, 17 reviews

Cottage in Oxford

Sailor's Cottage - Private Waterfront

Sailor's Cottage lets you get away from it all within walking distance of the charming and historic town of Oxford. This idyllic retreat on 29 acres is the perfect private hideaway for family and friends to enjoy the best of Eastern Shore living. The craftsman-built home is inviting and inspiring. Relax with your morning coffee on the screened-in porch, have cocktails on the dock, or take a paddle on protected Boone Creek. Longer stays are encouraged to take advantage of all there is to do.

4.89 out of 5 average rating, 47 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

5 out of 5 average rating, 18 reviews

Home in Tilghman Island

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.

4.95 out of 5 average rating, 82 reviews

Home in Cambridge

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.

4.95 out of 5 average rating, 21 reviews

Home in Cambridge

Relaxing Retreat on the Hudson

Escape to this stunningly renovated 5-bed, 2-bath waterfront retreat on Hudson Creek in Cambridge, MD. Perfect for small-large groups. Relax in the giant living room, cook in the gourmet kitchen, dock your boat at the pier, charge your EV at the garage, and enjoy the serene water views. 20 min from town - peaceful seclusion. The perfect balance of comfort and style for families, friends, or a memorable getaway. Fishing, Crabbing, Hunting, Writing, WFH, Yoga. Pet-friendly.

4.87 out of 5 average rating, 179 reviews

Charming Annapolis Water View Home

Floor-to-ceiling windows overlook the expansive Chesapeake Bay just 100ft away. Water views from most rooms plus treehouse vibes. 4 bed 4 full bath. Custom luxury upgrades, new kitchen aid appliances, rustic leather sectional sofas can sleep 4 more (14 total), outdoor grills, covered balconies, new hot tub, kayaks. Access to community fishing/crabbing piers/beach/picnic area. Close to beautiful Thomas Point & Quiet Waters park. A unique escape for nature lovers!

Guesthouse in Stevensville

4.99 out of 5 average rating, 278 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

5 out of 5 average rating, 57 reviews

Home in Oxford

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels.

4.98 out of 5 average rating, 128 reviews

Condo in Oxford

Cozy Oxford Getaway

Welcome to our cozy Oxford getaway. Located in the center of town, next to the Oxford Market, and across from the park. The apartment is centrally located and walking distance to all the restaurants, shops, and marinas. Oxford is a quaint little town that was founded in 1683. It was home to Robert Morris, the financier of the American Revolution.

5 out of 5 average rating, 7 reviews

Home in Chester

Kent Island Escape

At Kent Island Escape you can wake up to breathtaking views over the bay, sip cocktails on the spacious patio, and crab off your private pier! THE SUNSETS ARE OUT OF THIS WORLD. This 2-bedroom, 2-bathroom coastal escape is the perfect blend of relaxation and adventure, offering everything you need for an unforgettable getaway.

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Popular amenities for Talbot County Accommodation with Beach Access

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Apartment rentals with beach access

4.94 out of 5 average rating, 17 reviews

Apartment in Annapolis

Crow’s Nest Cottage - Down Under: Chesapeake Bay

RickRating, 5 stars3 months ago

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Apartment in Cambridge

5 out of 5 average rating, 12 reviews

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND

AmandaRating, 5 stars6 days ago

Larry's place was perfect. We were able to book with him last minute for the Eagleman and he was able to accommodate our needs. It was a pleasure to meet Larry and have him give us a tour of the home. He was a great host. Would recommend to anyone!

Private room in Queenstown

5 out of 5 average rating, 25 reviews

Couples River Retreat

KathleenRating, 5 stars3 weeks ago

We enjoyed the amazing view. Lots of things to do. My kids loved it that they didn’t want to leave. Highly recommend and would definitely go back next time.

Apartment in Oxford

Oxford Escape

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Holiday House Rentals with beach access

5 out of 5 average rating, 8 reviews

Home in Easton

Ferry Bridge House

ColleenRating, 5 stars5 months ago

Beautiful property - everything was just as advertised and more. Spacious bedrooms with comfortable beds. Quiet, private location with gorgeous views. The hosts were exceptional - very gracious, thoughtful and accommodating to any possible need. We were delighted to find the house so beautifully decorated for Christmas. It made for a very special stay. Thank you!

4.99 out of 5 average rating, 74 reviews

Captain’s Retreat! Newly Renovated - Beach House!

LisaRating, 5 stars2 weeks ago

plenty of towels. Great accomodations for a family wedding. Cards and games were available and appreciated.

5 out of 5 average rating, 38 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

Karina And ClintRating, 5 stars1 week ago

Gwen’s peaceful waterfront retreat was truly just that—peaceful and relaxing! From the moment we arrived, we felt welcomed and at home. Gwen was a gracious and responsive host, making sure everything was perfect for our stay. The property was filled with thoughtful touches and amenities that made our visit incredibly comfortable: a charming gazebo dining area, outdoor kitchen, a coffee bar, fresh flowers (such a lovely touch!), and more. The beds and bedding were comfortable, ensuring a great night’s sleep. The neighborhood is beautiful and quiet, with access to a private beach area that made the whole experience feel extra special. The highlight of our stay was undoubtedly the incredible dock experience—sitting right on the water, surrounded by nature, with comfortable chairs perfectly placed to enjoy morning coffee, afternoon sun, or stunning sunsets. Highly recommend for anyone looking to unwind in a serene waterfront setting!

4.88 out of 5 average rating, 52 reviews

Home in Cambridge

Waterfront, amazing views, pier, fishing/crabbing

SandyRating, 5 stars9 months ago

The house are clean, bright with a great view. We had a wonderful time and were lucky to have wonderful weather during our stay! We also had a lot of fun playing Mad Gab and other games in the games chest. We were successful in catching some fish and plenty of crabs. It was a great vacation. We enjoyed it very much.

5 out of 5 average rating, 7 reviews

Beach and bay views at one-level Waterfront home

BenRating, 5 stars4 weeks ago

This property is beautiful inside and out. You truly cannot beat the outdoor space. I could spend entire days sitting out back and looking at the bay. The interior was spacious and had everything you could need. Everything was clean and tidy when we arrived. The shower in the main bedroom was a particularly nice feature. The check in and check out instructions were clear and easy to follow. The host was perfectly communicative before and during the stay. I would not hesitate to book this property if you’re looking for a relaxing escape.

5 out of 5 average rating, 46 reviews

Away at the Bay: New Home on the Chesapeake Bay!

PaigeRating, 5 stars2 weeks ago

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

4.98 out of 5 average rating, 43 reviews

Annapolis Cottage at Bay Ridge, Renovated 2022

MarlysRating, 5 stars3 weeks ago

Perfect spot for our family of 4 to stay for my sons USNA graduation. We spent the whole week there. We enjoyed walking in the morning along the bay. We were able to watch the blue angels practice from the beach just down the street. All neighbors were so friendly. Quick trip to the academy for all the events. Home was nicely decorated and had every thing you could need and more. Thank you!