Pet-friendly vacation 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.

Lynda was truly kind beyond words. We were in town due to a family emergency and she extended such kindness and graciousness towards our family. Her home was truly an oasis for us during a very trying time. It was spotlessly clean, incredibly comfortable, and had everything needed and then some. She left delicious snacks for us and our pup. She helped with early check ins, late check outs, and made us feel like family. We will be back again and again. I cannot recommend staying here enough. It is worth every penny for the comfort and kindness you will feel in this beautiful home!

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

Our stay was really wonderful! Heather is a great host, responsive and friendly. Her home is super clean and nicely decorated, as well as spacious and private. We spent a day adventuring along the Blackwater River and this space was perfect to rest and recoup in. Would definitely return if we stay in Cambridge again and highly recommend!!

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.

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.

The house and surroundings are beautiful. Unfortunately, we had rain during most of our trip. There was plenty of room and board games inside the house. We were able to get outside and try crabbing and fishing one of our days. All of the supplies needed for cooking were in the immaculate kitchen. We would love to come back in the fall.

Ted’s home is amazing all the way around. We planned a trip for Father’s Day weekend. We crabbed, fished, grilled out, and went swimming in the pool. We played our family kickball game right out front. The house is perfect size for my huge family. It’s a old country style home in the woods with no neighbors peace and quiet. The house has plenty of accessories for cooking and eating crabs. Being a host myself of Airbnb this place is a must book! We can’t wait to book again this summer.

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.

It is NOT possible to find something negative to say about this property. Absolutely wonderful! Hubby and I went for a week to celebrate his retirement and Father’s Day. I really just wanted some peace and quiet from the chaos of the renovation influencers who recently moved in next to our home. Lol. This property has PEACE in spades! You’ll feel like the only people on earth. Yet nice restaurants and shopping are just down the road. The setting is beautiful. We spent much of our time on the screened in porch watching the abundant wildlife. We swam, canoed, explored and just relaxed. The house itself is amazing. So comfortable with tons of seating for everyone. The gorgeous kitchen has everything you’d need, and there’s an appliance closet filled with goodies. You have TWO Keurigs, Doug! Lol. Super comfy beds, awesome showers. You will not be disappointed. We hated leaving and will be back! Doug is super responsive, and couldn’t be nicer. You will not regret choosing this home ❤️

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!

We are repeat visitors! Love the homey atmosphere and lovely deck. Pretty gardens and such a nice walk to the Chesapeake Bay. Very easy living at Heather’s place! Hope to come again and visit!

Donna was a terrific host, responded to my questions promptly and the one level house worked really well for my group who was in town for a family wedding. My mom needed the room with the hand holds in the shower and all of us enjoyed the king beds in the other rooms. The view is spectacular and we loved having the option to sit on the front or side porch depending on the time of day. The kitchen was stocked with everything we needed. We also liked the way the living room was set up with plenty of seating for our group. I would recommend this house!

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.

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.

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!