Family-friendly vacation rentals in Saint Michaels

Stayed here with two of my friends for a long weekend and we had a wonderful time! Room was incredibly clean and very spacious, with a lovely kichenette. Staff were amazing, amenities like the pool and hot tub were great, and overall a great experience. Janee was also super helpful, kind, and responsive!

Brooke's place was fantastic and it was easy to communicate with her. Everything was clear and as expected. Thanks Brooke!

This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.

Doug”s house is exactly as described and his communication was impeccable. My family and I truly enjoyed celebrating my birthday at this property. The pool is huge and there are seven bedrooms to choose from. The master bedroom has a sauna inside the room which was an added bonus. The only thing I wish they had was an additional full bathroom for 7 bedrooms. There is one in master and one in the hallway. There is nothing negative I can say. Even the cleaner, April was the best. I would definitely rent again and actually look forward to renting again 😊

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

Great location with lots of locations walkable and nearby. Peaceful neighborhood and great place to stay. Brandon had lots of helpful recommendations for restaurants, bars, etc.

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!

Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.

We had a great stay in Silver Spring! Were visiting family and also doing some sightseeing in Washington, DC. The bungalow was well located, and the perfect size for our family of 3. Our tween daughter loved having her own room, and the full kitchen meant we could stock up on breakfasts and snacks. The Metro is close with easy access to DC, and the Sligo Creek trail was great for a walk.

Had a great stay! I was visiting DC for the first time with my girlfriend, who is a DC native for Mother’s Day weekend. The place was affordable and clean, just like the photos, and had everything I needed; free parking, WiFi, and even some refreshments, which was a nice touch. The location was super convenient and close to a lot of spots I wanted to check out. The only minor issue was the dogs and family upstairs being a bit loud at times, but we understood since the hosts live above and that’s to be expected. Miguel was very helpful and friendly throughout the stay. Would definitely recommend—10/10!

Monica’s little suite was cute. It was clean and tidy, with the basic amenities. The bedroom is tiny but the bed was super comfortable. The living room is more of a hallway with a little couch in it but it had a tv with lots of channels. The kitchen is large with all the dishes you might need but no condiments at, except salt and pepper, so if you plan on cooking, you will need to buy everything for your meals. There are some coffee pods and creamers and sugar, so you can start your day with a nice cup of coffee. There is a washer and dryer but you will need to buy detergent if you wish to do laundry. The area is a long walk, at least 45-60 minutes from the national mall and all those sights but a little closer to the Capitol. There is a whole foods about a 10 minute walk away, and a few restaurants. Monica was one of the most responsive host that I have ever dealt with. She was quick to respond to every inquiry and so helpful with our questions about the area. A comfortable stay!

Great stay in a cute duplex in Arts District. Very clean, updated apartment close to restaurants and shopping. Perfect spot for a weekend in Annapolis.

Ingrid was there when we arrived and was so personable! She was thoughtful when it came to having things for my girls to play with! Although we weren’t at the Airbnb much because our family lived right down the street, the beds were comfortable and my daughters loved the toy box! Thank you for having us and we’ll be staying again the next time we visit 🙂

We've stayed at Kopal's quite a few times - very peaceful neighborhood, very close to Lake Artemisia, which is lovely for walking, also very close to College Park. Great location. The house is always very clean, well-equipped and Kopal is so responsive.

Great place for families. Quiet and safe street. Just across the road from a wonderful park. Quick drive to local attractions and dining like Fells Point and downtown. Rafi is an A+ host with clear communication and local recommendations. We loved our stay; thank you!

Our stay in Tall Timbers was fabulous, much of it thanks to the care, detailed information, and lovely accommodations provided by our host, Robert. He communicated extremely well through the whole process from booking to check out. Nothing was a mystery and everything was as described or better. The house is charming and in a lovely wooded location. it's isolated but close to many amenities and short drive to historical attractions, local businesses, and the beautiful Maryland coast. We had a particularly wonderful visit to the Tall Timbers Oyster Ranch which is walking distance from the house. We highly recommend this location and send our thanks once again to Robert for his outstanding hospitality!

Great apartment, exactly as advertised. Plenty of nearby restaurants, super convenient to Georgetown, and Metro stop is only 10 minutes walk away. Loved it!

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

It was a great place to stay. The days we went were quite rainy, and the house looked like a homestay nestled in the woods. The house was kept clean, cozy, and quiet, just what I needed after a long tiresome day. I enjoyed their book collections as well. Although, I couldn't make use of the local suggestions they had in the house, I'm sure it was well-curated. Overall, a fantastic stay in a safe place.

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.

We've really liked the house with the pool and it was exactly what was show in the pictures. We really want to go back there next year

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!

House is amazing!! Everything was perfect and well organized!! Will definitely be back at this property. Excellent communication.

The place was perfect. It's really cool how they have landscaped - it feels like being in an oasis. We like private places, and this is it. Essentially, you have one large room upstairs, a bathroom downstairs, and we utilized the patio, a small kitchen, and a grill area as our combined kitchen and dining room. In fact, we liked the place so much we asked to stay another day and fortunately were able to. We will be back!