Waterfront holiday rentals in Talbot County

Find and book unique waterfront accommodation on Airbnb

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Popular amenities for Talbot County waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Private room in Cambridge
5 out of 5 average rating, 28 reviews

Waterfront Room at Happy Campers

FallonRating, 5 stars1 day ago
My fiancé and I had an amazing stay here! Brad and Roseann were great hosts and Brad was quick to respond when we needed anything!
Apartment in Cambridge

Cambridge Apt in Walkable Neighborhood

HeidiRating, 5 stars3 weeks ago
GREAT location within short time/distance for activities, dining and sites. The waterfront and near marina location made for beautiful, quiet walks and sunrises. Space itself set up well for time spent relaxing, cooking and sleeping; comfortable bedding, workable kitchen/dining area, A/C and ceiling fans located well to keep entire apartment comfortable. Would definitely stay here again!
Guest favourite
Apartment in Annapolis
4.94 out of 5 average rating, 17 reviews

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.
Guest favourite
Apartment in Wye Mills
4.77 out of 5 average rating, 66 reviews

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |

TimRating, 5 stars1 week ago
Host was responsive, rental was as pictures with no surprises and clean upon arrival. Would stay there again
Guest favourite
Private room in Cambridge
5 out of 5 average rating, 22 reviews

Farm View Room at Happy Campers

SarahRating, 5 stars1 month ago
Cannot say enough nice things about this place! Hosts were very welcoming (fresh cookies included!) and their space was incredibly relaxing. While the yard and outdoor amenities were shared with the other guests, there was ample space in the yard between the adirondack chairs, lounge chairs, and hammocks. Hosts also have kayaks, floaties, lawn games, and bicycles for guests to use.

Waterfront house rentals

Guest favourite
Home in Newcomb
4.98 out of 5 average rating, 53 reviews

Saint Michaels Waterfront Home

KaleighRating, 5 stars3 weeks ago
Beautiful location and home to spend over Memorial Day weekend. The house had everything we needed and was a comfortable stay. Brandon was very nice and accommodating.
Guest favourite
Home in Preston
4.95 out of 5 average rating, 98 reviews

River House on the Choptank

SandyRating, 5 stars2 weeks ago
The house was perfect for us. We were in town for grandson's graduation and needed extra space and this definitely delivered. The property was amazing. Even though we couldn't physically enjoy much outside activities due to the rain we did get to enjoy beautiful views of the river from the large picture windows. Steven was always quick to respond to messages which was much appreciated!
Superhost
Home in Grasonville
4.8 out of 5 average rating, 5 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

GinnyRating, 5 starstoday
Holly and Nash's home was clean, beautiful, and very spacious for 3 couples. Complete renovation and all new furnishings inside. As listed, all 3 bedrooms are downstairs, along with 2 1/2 bathrooms. The beds (3 queens) were comfortable. The kitchen is gorgeous for meal prep. Kuerig and coffee pods, Nespresso and pods, salt, pepper, dish soap and some spices were provided. Bring anything else you need. Beautiful new grill on deck. Upstairs (using a tight, spiral staircase) housed more seating another TV, pool table, wet bar and another full bath--basically, an adult entertainment area. Beautiful neighborhood. Bridges Restaurant in Kent Narrows (12 min drive) had very good food and service. We visited the cute town of St. Michaels (49 min drive). Communication with Holly was excellent. She was super responsive and helpful, provided suggestions and went the extra mile. Great stay
Top Guest favourite
Home in Chester
5 out of 5 average rating, 39 reviews

*Waterfront Sunset Bayview* sleeps 6

KellyRating, 5 stars1 week ago
The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)
Top Guest favourite
Home in Cambridge
5 out of 5 average rating, 34 reviews

• Peaceful Point • A relaxing waterfront retreat

KacieRating, 5 stars1 week ago
Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!
Top Guest favourite
Home in Cambridge
4.98 out of 5 average rating, 52 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

VictoriaRating, 5 stars1 week ago
One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.
Top Guest favourite
Home in Tilghman Island
5 out of 5 average rating, 18 reviews

Panoramic water views

MeganRating, 5 stars1 month ago
This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.
Guest favourite
Home in Neavitt
4.95 out of 5 average rating, 85 reviews

Waterfront, Dog friendly, St Michaels home

MeganRating, 5 stars8 months ago
Wonderful stay, house is beautifully decorated, clean and cozy. Enjoyed the adirondack chairs, fire pit and stargazing at night. We would certainly rent again!

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