Pet-friendly holiday rentals in Saint Michaels

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.

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.

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.

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 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.

We truly enjoyed our stay at the Colonial Beach Airbnb. The house is very cozy, well stocked, clean, updated and Carmen is a thoughtful host. The deck is a great area to relax overlooking the water and a few tried their luck fishing off the dock. Very nice!

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!

Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!

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 place is an absolute gem. We’ve stayed in everything from sleek modern homes to charming older properties, and this one truly stands out. Although built in the early ’90s, it has a unique colonial charm that feels timeless. The bedrooms and bathrooms were spotless and comfortable, with plenty of drawer and closet space for everyone. While it’s listed as a four-bedroom, there’s an additional upstairs room perfect for an air mattress, making it easy to accommodate up to 10 guests. What really drew us here was the peaceful setting—and it didn’t disappoint. The pool sits in front of the house, while the back opens to serene water views. Both areas offer spacious, covered and open seating to relax, rain or shine. In fact, we spent our first rainy evening on the covered back porch, just soaking in the view. We also brought our dogs, who absolutely loved having so much room to explore. The fully fenced yard gave us peace of mind, which made the stay even more relaxing. The hosts were

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!

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!

An ideal place for a couple (and in our case a dog) looking for a peaceful, relaxing weekend in a beautiful and convenient location.

This is our 2nd time here and again it has been a wonderful experience for my girlfriend and I. We highly recommend this place to anyone that is looking for a comfortable weekend stay. Mrs. Bonnie is very friendly and an amazing host. We would love to visit again.

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.

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!

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

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.