Beach house holiday rentals in Saint Michaels

Very roomy for a family vacation. Great location and covered porch was great for taking in views of river and enjoying summer breeze. Host was responsive and provided detailed instructions.

Less than .5 miles from sand . The kids loved staying at the house versus a hotel ! Was the perfect spot to relax and go on the deck to hear the water . Would definitely go back for another vacation.

We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.

My mom, sisters, friends and I enjoyed a relaxing fun filled time at the Coastal Oasis at the Chesapeake for our Mother's Day Retreat. The view is amazing and truly can be seen from every room in the house! Being able to see the beauty and calmness of the water helped each of us kick back and let the stress melt away. The big dinning room table allowed all of us all to enjoy breakfasts, dinners and touching conversations together. My guests loved the décor and raved about every detail. The beds and furniture were comfortable and house clean. I would definitely come back!

Came back for a third visit and had a lovely time at this peaceful retreat.

This was our second trip to Bob’s and we plan to return! The crabbing was great! Beautiful views and loved the lighting at night. Great hot tub! We loved having enough space for all of us to hang out in multiple areas. Nice upstairs balcony. Loved the kitchen! The kids loved splashing and playing at the private sand beach. Screened in porch was a very comfortable place to hang out! Can’t say enough good about this place!

Beautiful views, beautiful weather, plenty of beds and space for all the guests, close to some great seafood restaurants. A great secluded place which allowed us to let loose after a stressful year (we are teachers). I would recommend this place to anyone looking to decompress.

This home was the perfect way to spend a long weekend with our family and our dog! We enjoyed every amenity (the pool, the beach, the paddleboards, the sauna, the cold plunge, the grill, and even the steam shower!) and had a great time venturing into the nearby town. The home is well taken care of and you can tell that a lot of thought went into its set up. We'll definitely be back!

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

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.

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!

This home gave us something we hadn’t experienced before: a vacation with two small children that actually felt like a vacation! From the moment we arrived, we were blown away by how perfectly suited the home is for families with young kids. The pool has a shallow platform area that our toddlers could safely enjoy, and the expansive, beautifully maintained yard gave them plenty of space to run and play freely along with a swing and hammock. Inside, the house is just as exceptional. The layout is thoughtfully designed, with a separate bedroom wing that allowed us to put the kids to bed and then relax in the evenings without worrying about noise. Every detail felt intentional and welcoming, and the water views were absolutely stunning. The home is just a short drive from the charming town of St. Michael’s, which we loved exploring. This trip was such a joy for our entire family, and we’re already talking about when we can come back. Highly, highly recommend!

Our family loved our too-short stay at Jessica’s lovely home. Mornings looking out on the water and lounging on the outdoor deck were so tranquil. The home has a wonderful orientation and light-filled living area. Plenty of space, well laid-out and just about every convenience one needs in this comfortable abode!

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!

Great stay for our group. Comfortable beds, and well stocked home. Easy communication. Thanks! We’ll definitely rent with you again next time!

Nicki was an exceptional host—responsive, thoughtful, and truly dedicated to providing a wonderful experience. The home was absolutely stunning, equipped with everything we needed, and her attention to detail was impressive. She truly thought of everything, making our family trip seamless and memorable. The property was in pristine condition—immaculately clean, set in a peaceful and quiet location with breathtaking views. I honestly can't say enough great things about this home! As a Realtor, I will be recommending it to all my clients, family, and friends. We can't wait to rebook our stay there again soon!

Peaceful and private spot just a stones throw from the water. We enjoyed our stay and will be booking again next year! Cozy and comfortable oasis in the woods.

Our Airbnb stay was absolutely fantastic! My family and I really loved all the amenities. The waterfront view was stunning, and we had a great time grilling and just hanging out together with friends and family. It was truly a memorable experience! I would definitely recommend this Airbnb for a family getaway and to have a peaceful time enjoying the water and the beach. I definitely will come back again!

This was our second year in a row visiting Julya’s place! Our family loved it so much last year we booked as soon as we could for this season. The house was just as beautiful as we remembered, the kids even said it felt like home the second day. All the thoughtful things included are so nice (blackout shades for the kids, all the kids kitchen stuff, extras for all usable items, beach items). And we love the location! Easy to get to activities, we very much enjoyed the marine museum, the Imaginarium, fishing on the shea-d-lady, and sailing with Sail Solomons. Island Hideway was huge hit with the whole family for dinner. The house is an easy walk to the beach and the view is so cool, feels like a beach treehouse. Will hopefully be back again next year (if not at the end of this season!) 😁 Thank you Julya!!

The property, location, house set-up, and communications from the management during our 6 day stay was amazing. Literally the best low-key, relaxing experience I have ever had in recent memory. The house has everything you need for a great peaceful stay, especially if you are just hanging with a small group of close friends. Cooking is particularly awesome, as this property has a great wide open kitchen. The grounds are beautiful. We spent most of our time on the main floor in the kitchen and then on the long beautiful dock where we did some fishing and first time crabbing just for fun. The town nearby and neighborhood is so nice. Not far from Annapolis, MD at all if you want to visit. But honestly, the property alone is so nice to just to stay in and just relax. Great space with some homey accommodations. Big shout outs to one of the property management team members, Melissa. She was so very helpful. Will be back again next year!

We recently stayed at Colin’s Airbnb in Lusby, MD, and it was an absolute gem. Nestled right by the ocean, the home was quaint, peaceful, and filled with charm. The views and the serenity of the surroundings made our getaway feel truly special. Colin was a wonderful host—quick to respond, kind, and genuinely pleasant to chat with. When we reached out for local bakery recommendations for our daughter’s birthday cake, he gladly shared a few. We ended up choosing one and couldn’t have been happier—the cake was perfect! The home itself was cozy and comfortable. The IKEA bedding added a clean, modern touch and made for a restful night’s sleep. There was just the right amount of space for the three of us to relax and enjoy our time together. Thank you, Colin, for making our stay memorable—we’d love to return someday!

Karyn's home, nestled along the Choptank river, and just across from the original "Glasgow" estate dating back to the 1700s, is just charming. We used the three bedrooms and found everything cozy, comfortable and clean. The home is very well laid out with an inviting kitchen joined by chairs in front of a beautiful fireplace. There's also a TV area with a huge couch, plus bathrooms in every bedroom. Hats off, they are doing a great job with their BNB. We'll be back!

Our third year of staying at Jennifer’s cottage and studio. A lovely location for a beach weekend with our family and grandchildren. The accommodation is comfortable and well equipped, the cottage having a full kitchen and large sunny deck with BBQ. The studio is cozy and perfect for a couple. The community beach is a 2 minute walk, quiet and safe for young swimmers. We didn’t get to enjoy the hot tub or use the kayaks ( too busy with little kids!) but maybe next year!