Beachfront vacation rentals in Talbot County

Find and book unique beachfront homes on Airbnb

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Popular amenities for Talbot County beachfront rentals

Pet-friendly beachfront home rentals

Guest favorite
Home in Easton
5 out of 5 average rating, 8 reviews

Ferry Bridge House

ColleenRating, 5 stars4 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!
Top guest favorite
The living room features a cozy seating arrangement, including two armchairs and a spacious sofa adorned with various cushions. A large flat-screen TV is mounted above a stylish fireplace. Natural light filters through the window treatments, and a neutral-colored area rug complements the hardwood flooring.
Home in Cambridge
4.95 out of 5 average rating, 21 reviews

Charming Craftsman -Iron/EagleMan Start 2 Blocks

BrentleyRating, 5 stars2 months ago
Nice 100yr old house. Everything was great with our stay.
A serene sunset over the bay is captured, casting warm hues across the sky and reflecting on the water's surface. A wooden dock extends into the water, with a round blue float nearby, suggesting a relaxing outdoor space.
Cottage in 5, Bay Hundred
5 out of 5 average rating, 3 reviews

The Bayside Cottage STRN 23-3

BryanRating, 5 stars2 months ago
Nice, cozy place for two and a pup. Gorgeous views directly on the bay, especially from the bedroom. Very clean and stocked with everything one would need - nice furniture and the gas fireplace was lovely. Perfect spot for a quiet winter getaway.
Top guest favorite
Houseboat in Stevensville
4.94 out of 5 average rating, 51 reviews

Chesapeake Houseboat Getaway

RichardRating, 5 stars2 months ago
The houseboat was everything and more than the description. If you are looking for a great winter get away this is a perfect place to go to. You can kick back and relax or stay busy shopping and seeing the historical towns in the are. St Michaels and Easton are a short ride away. The restaurants are very good no matter what price range you are looking for. The shopping is great with many interesting small shops. I will certainly be back to the houseboat later this year.
Guest favorite
A cozy den area features a yellow sofa adorned with a blue accent pillow. A wooden coffee table sits in front, while a woven basket with a blanket is placed nearby. A record player is illuminated by a pendant light against a backdrop of calming wall art.
Cottage in Cambridge
4.98 out of 5 average rating, 43 reviews

Cozy 3-bedroom cottage steps away from the water.

AdamRating, 5 stars6 days ago
Beautiful, clean home ! Nice new appliances and comfortable stay !
A marina scene is captured with numerous boats moored alongside wooden docks. Calm waters reflect the boat masts and a soft pastel sky. Walking paths are visible along the waterfront, lined with grass and a few parked cars in the distance.
Townhouse in Cambridge
4.77 out of 5 average rating, 22 reviews

Cozy Townhouse on Cambridge Marina

KellyRating, 5 stars7 months ago
Perfect location. Amazing host. We will 100% be back!
Top guest favorite
Home in Oxford
5 out of 5 average rating, 41 reviews

Stewart Ave Retreat

AbbieRating, 5 stars2 weeks ago
Our stay was wonderful. Nanette, was an amazing host and extremely accommodating. The house is beautiful and great for dogs. The town of Oxford is stunning and the locals are very friendly. We definitely would stay here again!

Beachfront home rentals with a pool

Top guest favorite
A tranquil heated pool is surrounded by lush green grass and vibrant flower beds. Lounge chairs are strategically placed around the pool for relaxation. In the background, a stationary RV and a multi-story building complement the charming outdoor retreat.
Camper/RV in Stevensville
5 out of 5 average rating, 9 reviews

Charming RV With A Water View

CodyRating, 5 stars18 months ago
Andy was an awesome host! He checked in with us in the mornings to see if we needed anything (via text). They also had some great recommendations for us since we were out-of-towners. Would not hesitate to book with Alice and Andy again if we are ever in the area!
An aerial view of the St. Michaels Harbour Inn showcases a full-service resort nestled along the water. A pool area is visible, surrounded by lounge chairs, while boats are docked nearby, merging relaxation and waterfront activities.
Resort in Saint Michaels
4.4 out of 5 average rating, 5 reviews

St. Michaels Harbour Inn - Premium King WF Suite

MonicaRating, 5 stars52 months ago
If you’re looking for a getaway that is quiet and has a great view, this is a great place for you. Our suite was spacious. Loved the fireplace and the jacuzzi tub. Views of the sunrise/sunset on our balcony facing the marina was spectacular. It’s a very short drive and 10 min walk to the town’s Main Street. Local restaurants are fabulous! With it being off-season, the restaurants have varying hours so be flexible on what’s open and what you’d like to eat. This made for a great long weekend getaway.
Superhost
A spacious outdoor dining area is presented under a pergola, featuring a long wooden table set with plates and decorative items. Two comfortable chairs face a scenic view of the water, framed by greenery and a cloudy sky.
Private room in Trappe
5 out of 5 average rating, 38 reviews

The Anchorage Bed & Breakfast

TaashiRating, 5 stars31 months ago
I'm super picky but this place was exceptional. The space was immaculate. Wonderful stay. Beautiful property. Bright, spacious apartment complete with a kitchen, dining table and even washer and dryer. The bed was super comfortable and the shower had great water pressure. Breakfast was yummy! Very kind hosts who accepted a last-minute booking. Enjoyed sitting around the fire pit watching a beautiful sunset over the Choptank River. Easy access to various small towns in the area. Great experience and would definitely stay again!
Superhost
The home features a welcoming exterior illuminated by warm outdoor lighting, showcasing large windows and a spacious deck with comfortable seating. A pool and spa, glistening in green hues, are surrounded by lush landscaping, creating a serene evening atmosphere.
Home in Saint Michaels
4.5 out of 5 average rating, 10 reviews

10 Minutes to St. Michaels with a Private Pool

JoyRating, 5 stars4 months ago
We had a great weekend a gain. Enjoying Christmas in St Michaels. Your home is beautiful. We ate at Ava’s, Limoncello, Carpenters and Talbots. Shopped on Sunday. Highly recommend the house tour. She you again soon.🥰
An inviting bedroom features a pillow-top queen poster bed with striped linens. Two bedside lamps provide soft illumination, while a ceiling fan offers airflow. A comfortable lounge chair sits beside a wooden nightstand positioned near a window with horizontal blinds.
Cottage in Neavitt
4.87 out of 5 average rating, 23 reviews

Grandview - Cottage 1B, Queen Bed, Pool, Bay, WIFI

TyesRating, 5 stars7 months ago
A nice peaceful place to stay. Easy to get into town. A little tricky to find the first turn off the main road, but once you see the sign it makes sense. Would bring everything you need including ingredients to cook (sugar for coffee, salt, etc). But cleaning supplies are there and it's all very comfortable.
Guest favorite
A clear swimming pool is set in a spacious area surrounded by grass and trees. The water reflects the sky and landscape, with picnic tables visible nearby, providing a relaxing outdoor space. The cottage can be seen in the background, enhancing the serene environment.
Cottage in Neavitt
4.71 out of 5 average rating, 21 reviews

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

SophiaRating, 5 stars5 days ago
This is a beautiful little gem right by the waterfront and very close to St. Michael. We loved it! So cosy, relaxing and peaceful. The overall property is amazing. We will be back!

Private beachfront home rentals

Top guest favorite
A scenic view of the waterfront features a private pier extending into the water, with boats visible in the distance. Two lounge chairs sit on the grassy area, providing a relaxing space, while the shoreline meets the gently rippling water under a clear blue sky.
Home in Annapolis
5 out of 5 average rating, 30 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

PninaRating, 5 stars1 week ago
Gwen was one of the friendliest, most responsive, proactive hosts we’ve ever had. Fantastic place. Incredible views with your own private pier right on the Bay! Calm, peaceful, modern vibe in this well-appointed home. Everything was incredibly well organized/stocked. Best coffee and tea set up I’ve seen at an Airbnb. Huge, open kitchen and huge family room for relaxing as a group. Loved the swinging bench outside and the shaded cabana. Didn’t get to use the fire pit this time, but loved that there was one. Thank you, Gwen- we’ll definitely be back!
Guest favorite
A view from a window showcases a peaceful scene of the Choptank River lined with greenery. A large tree provides shade, while parked cars are visible on the quiet street. The soft light of sunset casts a warm hue over the landscape.
Home in Cambridge
5 out of 5 average rating, 14 reviews

"Riverside Retreat"

ValerieRating, 5 stars6 months ago
I had such a great stay at this property and Doug was a great host! The location is fantastic—it's in a friendly, welcoming community that's just a short walk to great restaurants and coffee shops, which was super convenient. The space itself was clean, comfortable, and had a cozy, inviting vibe that made me feel right at home. If you're visiting Cambridge, Maryland, I definitely recommend staying here—it’s the perfect spot for a relaxing getaway. Would stay again in a heartbeat!
A brick pathway leads to the front door of a charming house, flanked by vibrant blooming flowers in shades of pink and green. A red rocking chair is positioned on the porch, inviting relaxation amidst the lush landscaping.
Home in Cambridge
4.94 out of 5 average rating, 16 reviews

Charming Cambridge Home and Garden

LucRating, 5 stars19 months ago
We rented a week at Nancy’s house for Ironman Maryland. Wow, what a great place! This was by far the best house we rented for an Ironman, and we did a lot of renting. The house is just between the transition area and the Ironman village. Perfect for 2 couples. Plenty of space and privacy. You can park 2 and even 3 cars. You have a garage for your bike. Etc etc etc. I recommend this place any time. Luc
Guest favorite
The image captures a serene waterfront scene at sunset. A wooden pier extends into the Chesapeake Bay, surrounded by rocky shorelines and lush green grasses. The sky displays soft hues, while the sun descends on the horizon, creating a tranquil ambiance.
Home in Tilghman Island
4.97 out of 5 average rating, 38 reviews

Tilghman Retreat: A house on the Chesapeake Bay.

Elizabeth ReynoldsRating, 5 stars4 months ago
This was our 4th time sharing this great property. The house has all you need, plenty of places to get some private time. We love the backyard, fire pit, pier and gorgeous views. This year we brought a soccer net. You cannot beat this place.
Top guest favorite
A wooden dock extends over the water, featuring two white Adirondack chairs positioned for relaxed seating. The serene water stretches toward the horizon, while the sky is dotted with fluffy clouds, creating a calming outdoor retreat.
Home in Chester
5 out of 5 average rating, 34 reviews

*Waterfront Sunset Bayview* sleeps 6

MaryRating, 5 stars1 month ago
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!
A bedroom features a spacious bed with light bedding and a decorative throw. A wooden dresser is positioned next to the bed, while a lamp provides ambient light on a small table. A cozy chair is located in the corner by a window, enhancing the calming blue walls.
Apartment in Oxford
5 out of 5 average rating, 3 reviews

Town Creek Hideaway +Boat Slip

DarylRating, 5 stars5 months ago
There were a lot of thoughtful touches- the bathroom had everything I could have needed. The kitchen was fully stocked and everything I wanted for my morning coffee was all set. The apartment was comfortable and complete. The neighborhood is nice and quaint- I love the cottages and historic buildings of Oxford. Thank you for giving me extra time on Sunday before my performance.
Top guest favorite
A wooden pier extends over gentle waters, surrounded by rocks. The scene is illuminated by a soft pink and orange sky at sunset, reflecting on the water's surface. Additional pilings can be seen in the distance, enhancing the tranquil setting.
Home in Cambridge
5 out of 5 average rating, 28 reviews

• Peaceful Point • A relaxing waterfront retreat

AnnaRating, 5 stars2 weeks ago
Joanna was an excellent host, and the home was such a beautiful, quiet retreat for our family while we were attending a wedding in the area. The home was beautiful and cozy, and the scenery outside was so calming. We wished we could have stayed longer, and we hope to book again for fun some other time!
Top guest favorite
A serene outdoor space features white Adirondack chairs arranged on a wooden deck facing Pinks Pond and the Choptank River. Lush green grass and blooming trees enhance the tranquil environment, providing a peaceful retreat for relaxation.
Home in Cambridge
5 out of 5 average rating, 83 reviews

In Town Waterfront Nature Retreat in Cambridge, MD

HarmonyRating, 5 stars3 weeks ago
If you’re looking for a tranquil, beautiful and well organized home away from home, this is the place! The view is spectacular, the property is pristine, the house is cozy but not cluttered. If you need it, Lia thought of it AND labeled it so you can easily find it! We had a lovely time with our family here, and we would definitely return! Book it while you still can!

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