
Waterfront holiday rentals in Talbot County
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Talbot County
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Talbot County
Waterfront apartment rentals

Waterfront Room at Happy Campers
What a special place this is! The property is beautiful and well-maintained and the view is incredible. Brad and Roseanne are lovely, friendly people and great hosts, ready with good recommendations on everything you might want to do during your stay. The area is great for cycling (even for road-averse folks like myself!) and kayaking or even just lazing around with a good book. Can’t wait to go back!

Cambridge Apt in Walkable Neighborhood
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!

Crow’s Nest Cottage - Down Under: Chesapeake Bay
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.

⋘ Lakeside Apartment ⋙| Private+Cozy Setting |
Location is quiet and tucked away. Clean and has everything you need. Close to The highway for easy access to eastern shore towns.

Happy Campers Waterfront Suite
From beginning to end the stay was amazing! Super helpful hosts. The area is absolutely beautiful, super private, and peaceful. You can really tell they care to give a great experience when you’re staying here!

Farm View Room at Happy Campers
Brad & Roseann's Airbnb was beautiful, well-organized and offered a plethora of activities around their property. The views were breathtakingly beautiful! It's essential to stay outdoors for the sunsets. We stayed for 5 days. They were exceptional hosts, very friendly and a delightful couple to meet! They were extremely prompt in their assistance, regularly checked in on us and provided valuable insights on local activities. We highly recommend Brad & Roseann.
Waterfront house rentals

River House on the Choptank
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!

Waterfront, amazing views, pier, fishing/crabbing
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.

Tuckaway Cove. August openings & a new kitchen!
Seven college friends spent a long weekend at Tuckaway Cove to celebrate our 65th Birthday year! We could not have asked for a better location or have had better accommodations! The decor was beautiful, and the home was spacious enough for us play games in the dining room or screened-in porch or to spread out when we needed a little reading time! We are all foodies so cooked several meals while there and we were all jealous of the newly renovated, high-end kitchen! We never expected to be able to be in the pool as much as we were although a pretty severe storm passed through while there. Annette reached out to see if we were all okay! She also offered us recommendations for dining out. We were close to Easton as well as St. Michael's and had the opportunity to explore both of those towns. The whole experience was just wonderful! We had a truly amazing opportunity to share some fabulous memories with friends in an unforgettable setting!

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

Gorgeous, waterfront home - Perfect for Families.
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.

Waterfront Chesapeake mansion - Panoramic Bay view
We stayed in this house for our son's Naval Academy graduation/commissioning. It was absolutely perfect for our group. The drive across the bay bridge took anywhere from 35-45 minutes depending on the traffic. At no time was the traffic as bad as we've experienced it on the DC side of Annapolis. We crossed the bridge 1-2 times a day during our 7 day stay. As soon as you get to the island and head south there is no traffic and it's a beautiful, peaceful drive. The house is perfect for entertaining with two large rooms inside on the main floor. There is a large island in the kitchen room which makes for a great serving area. It rained during about half of our visit so we made good use of the space indoors. Our children used the fishing poles, kayak, soccer nets, ping pong and fooseball table. Negin was very responsive in answering our questions and even worked it out so we could check in early. We would definitely stay there again if we had the chance.

Waterfront, Dog friendly, St Michaels home
Wonderful stay, house is beautifully decorated, clean and cozy. Enjoyed the adirondack chairs, fire pit and stargazing at night. We would certainly rent again!

Relaxing Retreat on the Hudson
Took the family here (grand parents, 2 babies). We had a great time. Mike's place was clean and modern and well designed. It was well equipped for getting some work done remotely. The family enjoyed catching a bunch of crabs and harvesting some oysters right off the dock in his backyard. Mike was also very responsive to any questions we had. Would def come back at some point in the future.
Destinations to explore
- Beachfront rentals Talbot County
- Rentals with a firepit Talbot County
- Rentals with a kayak Talbot County
- House rentals Talbot County
- Rentals with breakfast Talbot County
- Rentals with a washing machine and dryer Talbot County
- Rentals with pools Talbot County
- Rentals with outdoor seating Talbot County
- Flat rentals Talbot County
- Pet-friendly rentals Talbot County
- Rentals with a patio Talbot County
- Rentals with beach access Talbot County
- Rentals with a fireplace Talbot County
- Rentals with a hot tub Talbot County
- Family-friendly rentals Talbot County
- Rentals with lake access Talbot County
- Waterfront rentals Maryland
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Patterson Park
- Washington Monument
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Meridian Hill Park
- Library of Congress
- Quiet Waters Park
- Six Flags America
- Flounder Pavilion Beach Front - Sandy Point State Park