Pet-friendly holiday rentals in Saint Michaels

This was our third trip to this home, and we still love it! The home is exactly as described and walkable to everything in town. We appreciate that we were able to bring our dog to enjoy it as well. Is a quiet retreat that we fully enjoy.

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

A great stay on the river. The kitchen was well equipped and the rest of the house was comfortable. The screened in porch and access to the dock/beach/river was our favorite part. Our dogs were in HEAVEN. The location is rather remote, so recommend bringing any food you'll want as there are no close stores or restaurants.

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.

We had a great stay! The yard was perfect for our dog and playing with our grandson. There was plenty of water and the house met all our needs. The neighborhood was fantastic and we loved taking walks and seeing everyone else out walking their kids and dogs! Definitely will come back!!

This house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!

Cannot say enough great things! Incredibly understanding, great communication and loved the space! 100% recommend!

This home is just as advertised...it is very large, great for several families vacationing together! Our group was small so we didn't even make use of all of the space. The house is right on Tanner Creek which is just beautiful for sitting on the dock and relaxing, paddleboarding and kayaking, birdwatching, etc. It's also about a mile from Lookout Point State Park which is absolutely gorgeous. Restaurants and grocery stores are few and far between in this area, so it's a good idea to bring your own food, and the kitchen is well stocked with pots and pans for cooking. If you are looking for a place to relax in a calm and beautiful setting, this is it!

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

The house was beautiful and clean. The lication was great! Too bad it rain during out stay so we couldn’t enjoy the pool and the backyard. Thank you!

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

Heather's place was as described. Clean and neatly organised. The linens and towels were very clean. The facilities available were adequate. The kitchen is not a full kitchen but has enough for heating. We had left some medicines behind and Heather and her team spotted it, and communicated the same to us. In addition, they took the trouble to drop it off at the local FedEx office.

Cute & spacious boho apartment. My family of 5 was very comfortable inside. Metro & restaurants were close by (5 min or less walk). Free parking pass was great. Currently there is a lot of construction happening in the parking garage and on the street but it wasn’t too loud and once you got used to the few streets that were closed it was easy to drive and walk around the neighborhood.

My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!

We LOVED the space! We’ve been working on downsizing and the layout and hidden storage areas were exactly what we want in our future home. It was so, so comfortable. So much so that we never did use the hot tub that we really wanted to use 😂 We enjoyed the space and just vegged. We were doing Safety Patrol for the Bay Bridge Swim and there was plenty of room for our jet skis & double trailer. Wonderful hosts. Even joined us on the pool deck (upon invitation) for some friendly conversation. Cinnamon the golden was a sweetie too. Wonderful experience. Don’t hesitate to book. You won’t be sorry.

We absolutely loved our stay here! The space was the perfect getaway for us and our pup especially loved all the walks nearby the property! The space was clean and well-decorated and felt like a relaxing escape from the city. Martha was very responsive and gave great recommendations for places to eat and take hikes. She even provided treats for our pup, which he loved! We are definitely coming back soon!

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.

A wonderful spot for a weekend getaway! Super clean, charming, and cozy. Peaceful nature and views yet not too far from town. As so many guests have mentioned, the winery next door is lovely and makes for a fun outing. The cabin has everything you need and more! Highly recommend!

Bonnie’s cottage was perfect for my trip to Cambridge. Tucked away in a nice quiet spot. Very easy to get to the downtown area including parks, restaurants, and waterfront. Bonnie and Chuck are super friendly and helpful.

This place was amazing. It was well equipped, clean, a great view and close to many attractions and restaurants. It was so peaceful being on the water.

We absolutely love Loon Cottage! It was our second Memorial Day trip to the cottage and it’s so special. We love the decor and they had wonderful toys and games for our 5 and 2 year olds to play with. The outdoor area is also so magical for golden hour bbqs and our city kids loved running around. Location is close to lovely Easton and all that the Eastern Shore has to offer. Thank you for a great stay, we’ll be back!

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.

This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back

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.