Pet-friendly holiday rentals in Talbot County

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.

My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!

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.

The place was wonderful. The house was clean. The beds were comfortable. The kitchen was more than well equipped. The setting was beautiful. The outdoors was perfect. Great outdoor furniture. The Bayview was unbelievable. The house in relationship to recreation is spot on. I can’t say enough great things about the place. I will definitely be booking again and again.

Although we had been to Maryland before on holidays, we hadn’t been to the Eastern Shore before and we loved the location and the incredibly friendly locals who made us feel very welcome. The pace of life suited us just fine as we’re rural folks too. Many happy memories made and special shout out to Jacob at the nearby Neck District Grill for feeding us so well!

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.

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.

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

Catherine’s place was perfect location for Ironman eagleman. We were able to walk everywhere we needed to go. The place was clean, quiet, and comfortable. Being able to cool off in the pool was great. They were very friendly and I would stay again.

Amazing host! We had a great stay over the weekend for 70.3 Eagleman. The property was incredible, house was perfect and had everything we needed. Highly recommend to anyone looking to stay in the are! We will be back in the future!!!

Thank you so much Mariana and family! Wonderful stay with an epic half ironman finish to end an amazing weekend! Would 100% recommend for a peaceful weekend!

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.

David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.

Fantastic house if you’re looking for a private getaway! Our dog loved running around the property, chasing rabbits, and we all enjoyed how secluded it was. The amenities are exactly as described and we would absolutely rent here again.

Jenny was a great host. She provided proactive and responsive communications and made our stay easy. Everything was clean and in great condition, and there was plenty of space both inside and around the broader property, a perfect escape for the holidays for my family and my brother’s. The place is infant/toddler and dog friendly. We also appreciated the late checkout, not a necessity but a rare, appreciated convenience. We would definitely look to stay here again!

The place was perfect and we loved watching the sunrise over the bay every morning. Nice quiet neighborhood and great fenced in backyard for the dogs. The house was as described and looks like the photos. The host was very responsive and helpful! Would definitely recommend this home to anyone looking to come to the Annapolis area.

Everything was in order and as described. Good location. Would book again when around.

We had a delightful stay at Nick’s place. The interior is unbelievably charming- it is clear that they have an eye for interior design! There were plenty of towels, a well stocked kitchen, and plenty of basic necessities. The beds were comfortable and the host left helpful instructions for the area and home. 10/10 we would come back again!

The house/setting was even better than pictured. It was really charming and comfortable without being over the top. There was everything we needed, including the kayaks which were a big hit with my family. Great kitchen, really comfortable bedrooms with beautiful water views. The location is perfect, close to both Easton and St. Michaels. We look forward to staying there again when it’s a bit warmer so as to take advantage of the outdoor seating on the spacious lawn. Lisa was beyond responsive and helpful.

Truly a wonderful place, only wish that our stay had been for longer! The home is a jewel - clean and spacious with updated amenities, beautiful views, outstanding features like a gorgeous backyard with small vegetable garden and a fire pit (we made s'mores!) and bikes to take us everywhere around the area. We would definitely rent again!

Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.

We loved Ryan's cottage! The house has a super great feel and overlooks the lake with the most beautiful views, we extra loved that!! We definitely felt like we found a gem, you check in and there is nothing to worry about, it is super clean, the couch and bed looked small in the photos but were extremely comfortable and every room is equipped with everything you need to feel at home-extra linens, plenty of towels, wash clothes, cleaning supplies, toiletries and coffee!! The location itself was perfect for our travel needs and it is closer to Target, Food Lion, Acme, Safeway, Walgreens, liquor/wine stores. And the other great part, Ryan is extremely communicative so you know he's there and he has an adorable fur family. We would have squeezed in another day or two just to enjoy this relaxing space and highly recommend it for anyone looking for a nice place to stay. Thank you, Ryan!

Kathleen's place is perfect for a quiet peaceful vacation. We were there for a celebration and it offered something for everyone, a workspace to catch up on some work, hangout space in the lounge and also outdoors, and TV if you were so inclined. Kitchen is super well equipped and everything is spotless. Kathy was very responsive to any question or request. I highly recommend this place, we had a wonderful time.