Pet-friendly vacation rentals in Saint Michaels

Gorgeous place with lots of kitchen items stocked. Pool and hut are such an added bonus. Place was so clean and cozy. Being on the water was wonderful as well. Great location to town and Tilghman Island. Would definitely recommend this rental.

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!

What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!

We had such a wonderful stay! The house was beautiful, peaceful, and had everything we needed for a relaxing getaway. The layout was perfect for spending quality time together while still giving everyone space to unwind. Private beach access made it even more special—we made great memories, met some lovely neighbors, and even had a chance to paddle board and spot a stingray! Huge shout-out to Leigh, our amazing host—so thoughtful, responsive, and kind. We’re so grateful for the experience and would absolutely stay here again. Highly recommend!

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.

Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!

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.

Martha's place is a lovely retreat. There is enough privacy between the main house and the guest house. The guest house is spacious and comfortable with a great screened in porch and access to the pool. It's in a quiet and peaceful area. I look forward to coming back again.

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.

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

I loved this spaced, Brandon made sure to have all the amenities listed, but he doesn’t stop there. He pays attention to his guest needs and has even the little extras a guest may have forgotten. Such as the kitchen, I loved that his kitchen is stocked with all your needs. I love that he has everything labeled around the home so there’s no guessing. Bathrooms were spotless and also stocked with his quests needs as well. Fantastic is all I have to say! What a great host Brandon is, and his commutations style is on point!!

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!

Our stay at Justin’s Hot Tub Haven in Annapolis, was exactly that…a haven with a much enjoyed hot tub! Justin was exceedingly responsive, proactive, and flexible. The home is very well appointed with all the necessities, plus all the thoughtful touches like umbrellas, a doggie waste station, and bath robes to name a few. Our children loved the downstairs space (and secretly the adults were thrilled they had it too), and it felt to them like they had their own little apartment. The backyard felt like a small resort. We loved the quick walk to shops and the our boys loved the nearby basketball courts and baseball fields. We highly recommend this home and will stay here again!

The place was wonderful. It was wonderful timely responsive My Children enjoyed themselves. My wife didn’t complain and she loves to complain so she didn’t have one complaint which made everything absolutely perfect and I would definitely book there again in the next time I visit Maryland. It was wonderful experience.

This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!

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.

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.

We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!

Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.

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!

We had a wonderful stay at this well-appointed, cozy, and impeccably clean home. From the moment we arrived, it was clear that every detail had been thoughtfully considered—from the comfortable furnishings to the fully stocked kitchen and fresh linens. The space felt warm and inviting - perfect for relaxing after a long day. Communication with the host was smooth and responsive, and check-in was a breeze. I would absolutely stay here again and highly recommend it to anyone looking for a peaceful and comfortable getaway.

The place is absolutely gorgeous. Unfortunately, even though it is waterfront there isn't a good way to access the water for swimming or kayaking due to the way the breakwall is structured.

One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.

We were looking for a relaxing getaway, and saw an opening at this property. Booked for two weeks, and thoroughly enjoyed our stay… Very large property on the water.. fields and wooded, very quiet, very peaceful. A long dock with a great view of the bay. Supermarket nearby, a couple of very good restaurants. Richard had the house stocked with literally everything needed…. All we provided were groceries! Ducks, geese, herons, ospreys, egrets, songbirds, and several deer provided daily entertainment. Communication was excellent, responses just about instant. Got a chance to meet Mark, who provided some interesting history of this family property. To sum it up, highly recommend!!!