
House vacation rentals in Talbot County
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Top-rated house rentals in Talbot County
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Popular amenities for Talbot County house rentals
House rentals with a pool

Tuckaway Cove Relaxing waterfront property
I have only praise for Annette. However I am unhappy with this app’s policy of not allowing me to use a gift card for the final payment. They automatically charged me without notifying me when payment was due. Once done unable to reverse or credit account. Knowing that the gift card has an expiration date it now makes our once a year usage difficult.

Gorgeous, waterfront home - Perfect for Families.
We had the most beautiful Thanksgiving gathering at Casey’s Porch on the bay for an extended family reunion. The house is lovely - spacious, gorgeous and cozy at the same time. The views on the water were amazing. There were plenty of beds and ‘hang out’ spots for our tweens and teens, and 3 private baths for the adult couples were much appreciated. And our hosts could not have been more helpful and friendly. Thank you for giving us this opportunity to make more happy memories together!

Waterfront Farmhouse Meets Modern Luxury
We had a wondferful time with extended family at this beautiful spot where you're surrounded by nature and expansive views from inside and outside the house. The views of the water and sunsets are breathtaking. The house has everything needed to cook family meals and share a comfortable and revitalizing time.

Relax by the Water - Summer Dates Available!
Absolutely beautiful home! highly recommend!

Wildbluesea Retreat
We came to the area for a wedding and had 8 adults and 2 children. There was plenty of room and everything was very clean and welcoming. There was a large table for all of us to fit at and eat together and we especially enjoyed our time in the hot tub. Janean was very quick to respond and gave us great recommendations for dinner. The area was beautiful and we would definitely love to come back some time in the future and stay at the Wildbluesea Retreat!

Waterfront Private Dock & Pool Near Cambridge
I first stayed at this lovely house back in February 2021 during peak pandemic and had such a lovely time. Came back for a short trip to visit some family in the area and was happy to rebook this gorgeous property. We had plenty of space for our large group and the place was well stocked The hosts were wonderful, I had a quick question for them and received a response in literally less than 5 minutes. This is now my go to Airbnb on the eastern shore, looking forward to my next stay with them!

Waterfront Bliss: Ultimate Tilghman Retreat
Keith was so super sweet! Always texted back if I had a question. He was welcoming since our first contact. The house was amazing. It felt like home and we treated like home. Definitely will be back again. Absolutely stunning!!
Weekly house rentals

Peaceful Waterfront Home in Annapolis 3BR 2BA.
We really enjoyed staying at this home. Such a beautiful view and extremely peaceful. Gwen was a great host. We would definitely stay here again.

Chessie Cottage - Chesapeake Bay
Fabulous place. The amenities were beyond the description to ensure total comfort in the beautiful space. Views from every room. We don’t return many places, but we will this one.

Unwind on the Wye River
beautiful spacious home. great for my family of 6 to meet up with our USNA midshipmen. loved the back yard and living rooms

*Waterfront Sunset Bayview* sleeps 6
Beautifully designed house highlighted the stunning view of the bay. Cozy and clean, couldn't have asked for more!

Cozy & Spacious, The Calway Inn
Cozy house, very comfortable, easy to find, near enough to major roads to be convenient for exploring, but quiet and private. Jefferson was super easy to work with. A real find.

• Peaceful Point • A relaxing waterfront retreat
This property was wonderful. We were there with another couple. The home was well appointed including a lovely coffee area. Well designed, nicely decorated that was up to date and clean. The view was wonderful. We enjoyed the towns of Cambridge, St Micheals and the Blackwater Preserve.I would definitely come back again!

Eastern Shore Retreat!
Courtney is super responsive and a great host!

Private&Cozy/3br+2ba/1mi to town
I have never stayed in a place that absolutely had everything we needed. I could have brought my clothes, shoes and makeup and basically been fine. The house was very clean. The furniture was comfortable and clean. The beds were comfortable. Town was 5 minutes away. We loved the shops and great restaurants. We would definitely recommend this house.
Private house rentals

Ironman Home-1.5 miles from finish line
Great location for Eagleman 70.3! The home was beautiful and right on the run course for spectators! The home was a quick and safe walk to the race start at Gerry Boyle Park! Jordan was incredibly responsive and warm and welcoming!

Your “Happy Place”
Loved the place & Tilghman Island Great Retreat Close to St Michaels, but more laid back

Crab Alley Bay House, Waterfront Home w Hot Tub
Kathryn's place was clean and beautiful! Kathyrn provided many thoughtful amenities such as sound machines, night lights, and coffee for the coffee maker. The house has a great set up, especially if you are looking for somewhere fun to spend a holiday! The kitchen would be great for a lot of cooking, and the beautiful dining room table has enough room for a lot of guests. We truly enjoyed our stay and hope to be back!

Charming 4 bedroom in Historic Cambridge
We had a great stay. Kristin was very friendly and responsive through the booking process, leading up to our stay and during our stay. The house is very spacious and worked well for our multi generational family. It’s an older house but tastefully updated with modern amenities. We were unable to take advantage of it, but the house was within walking distance to a cute downtown area with a lot of restaurants.

Water View Home in quiet neighborhood
Julie and her husband were amazing. The house is the nicest I have ever stayed in as an Airbnb. It had everything you could ever need and more. Felt like a luxury hotel and I am particular! Highly highly recommend!

Crew's Quarters | an ESVR property
Great place to stay for a girls get away!!! The place was gorgeous and beautiful laid out. The host was extremely responsive throughout our stay with any questions or requests for recommendations. The process to check in/out was extremely easy. The town of st michaels is beautiful, quaint and plenty to do! Lots of good restaurants, walking trails and beautiful views of the water in town. Thanks for a great stay!

Private Beach Front Marina House
I recently stayed at this lovely place and had a fantastic experience. The host was incredibly friendly and responsive, making the whole process smooth and enjoyable. The property itself was perfect for a family holiday, with plenty of space and amenities to accommodate everyone. It truly felt like a home away from home. Highly recommend for anyone looking for a comfortable and welcoming place to stay with their family.

Two Oysters House 2025 Remodel
We had a great stay in St Michael’s at the Airbnb. Close enough to town (we were there for a wedding) and the view of the water from the dock is beautiful. Spacious home with a nice screened in porch. The bedroom connecting to another bedroom was a little odd but it wasn’t a surprise as it was explained in the listing. Overall, great place to stay.
Destinations to explore
- Rentals with a kayak Talbot County
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- Pet-friendly rentals Talbot County
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- Nationals Park
- The White House
- National Mall
- Hampden
- National Museum of African American History and Culture
- Sandy Point State Park
- Smithsonian National Museum of Natural History
- Big Stone Beach
- Smithsonian American Art Museum
- Six Flags America
- Washington Monument
- District Wharf
- Patterson Park
- National Harbor
- Oriole Park at Camden Yards
- National Air and Space Museum
- Meridian Hill Park
- Heritage Shores
- Killens Pond State Park
- M&T Bank Stadium
- American African Museum
- Lincoln Park
- Crystal Beach Manor, Earleville, MD
- Gerry Boyle Park