House holiday rentals in Saint Michaels

It was amazing.The pool is so fun.We had bad weather but we were still a little inside.The location is quiet and beautiful. We will come back for sure. Thank you

Connie’s place was great! Looked just like the photos. The house was clean and in a great area. Nice and friendly neighbors. We enjoyed the community beaches that are super close, clean and dog friendly. It was a prefect weekend trip. We would book here again!

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

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!

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.

This home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

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!

Beautiful place with a lovely spot on the south river. Loved the views and how the space allowed the views to really shine. Comfortable, clean, would stay again if I come back to the area. Very peaceful and what I was hoping for. (And not far to town/other things either!)

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

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!

Nate's house was perfect for our purposes. The neighbourhood is very quiet and peaceful, but you are less than 10 minutes from grocery stores, restaurants and other amenities. The house itself was exactly as described, and had everything we needed, with plenty of space. It was clean, comfortable and well-equipped. Nate was a very responsive and proactive host. We would definitely try to stay here again if we are in the area.

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

The perfect mom and teen boy getaway! The house is on the water with gorgeous sunsets and super clean! My boys attempted fishing daily even without any luck. Altho we didn't kayak because of the choppy water, its great location (there's a ladder at the private pier or a public launch a few yards away) We cooked and ate in a few nights and also enjoyed a local spot on the water (The Narrows). The neighborhood was quiet, relaxing and peaceful. We enjoyed a visit to the Chesapeake Environmental center (abt a 12 min drive) which was a hidden treasure. The Chesapeake Outdoors (recommended by our host Jeremiah) was a great find for bait and info from the locals. Morning coffee on the patio and evening sunsets on the pier were some of my favorites, along with the spacious open floor plan (yet privacy with bedrooms). Jeremiah was super responsive and kind! We'll be back to kayak, fish more, enjoy the hot tub coming soon, the serenity and gorgeous sunsets! (maybe we'll even bring dad -LOL)

Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!

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

Lynda’s place was the perfect spot for our mother/daughter/dog weekend getaway to Easton. As my daughter said, staying at Lynda’s house was like “being in a big hug”. Everything was so clean and comfortable. Lynda provided us with all the comforts of home including lots of local goodies in the kitchen to eat and drink. She even bought a special dog treat and had water and food bowls and a dog blanket for the sofa for our pup. Not only was the house welcoming to our dog, but right across the street is a wonderful rail trail walking path which made dog walking a breeze. I highly recommend visiting Easton and staying at Lynda’s!

Holly and Nash's home was clean, beautiful, and very spacious for 3 couples. Complete renovation and all new furnishings inside. As listed, all 3 bedrooms are downstairs, along with 2 1/2 bathrooms. The beds (3 queens) were comfortable. The kitchen is gorgeous for meal prep. Kuerig and coffee pods, Nespresso and pods, salt, pepper, dish soap and some spices were provided. Bring anything else you need. Beautiful new grill on deck. Upstairs (using a tight, spiral staircase) housed more seating another TV, pool table, wet bar and another full bath--basically, an adult entertainment area. Beautiful neighborhood. Bridges Restaurant in Kent Narrows (12 min drive) had very good food and service. We visited the cute town of St. Michaels (49 min drive). Communication with Holly was excellent. She was super responsive and helpful, provided suggestions and went the extra mile. Great stay

The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

Loved my stay beautiful home with serene surroundings and lots of local historic attractions. Highly recommend James’ place!

I had an absolutely wonderful stay at this beautiful home. The house itself is spacious, beautifully decorated, and incredibly comfortable. It was fully stocked with everything I needed — from kitchen essentials to high-quality linens. The beds were super comfortable, and there were more than enough towels and washcloths for everyone. One of the standout features was the in-home gym — much more equipped than I expected, which was such a bonus! The second floor, where the bedrooms are located, felt like a private retreat, and the land surrounding the property was both aesthetically stunning and very peaceful. This home truly exceeded expectations. I would absolutely stay again and highly recommend it to anyone looking for a relaxing and luxurious getaway.

Nicole was a great host. Her place was nice — uncluttered, kitchen had everything you need, it was nice sitting on the sofa and looking out at the water. The beds we very comfortable.

Beautiful place, beautiful location. Joel thought of anything you could want.

My stay was absolutely incredible truly beyond anything I expected! One piece of advice: definitely have transportation, as the property is on an island and things are a bit spread out. That said, I enjoyed a lovely walk into town where I dined at some charming local spots and even did a little boutique shopping. Be aware that Uber and Lyft aren’t readily available in the area, and when they are, they’re pretty pricey. But honestly, the property itself feels like something straight out of a Lifetime movie peaceful, picturesque, and exactly the kind of escape I didn’t know I needed. I can’t say enough good things about this stay… so I’ll just say: BOOK IT!