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.

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!

This was a great house for our teammates to stay in for the weekend!

Our stay was great. The house is located in a quiet friendly neighborhood. The views are amazing. The house is very comfortable and so relaxing. Loved that three bedrooms each had a bathroom. The hosts were wonderful and very responsive.

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!

This place was a real treat. It was breath-taking, inside and out. The location was spectacular with amazing views thanks to the wall of windows in the great room. Usually the sofa bed area is not the best room in the house, but this time it was super comfortable and came with the most amazing sunrise. We will definitely be coming back here.

Andrea was so responsive from day 1 when I had questions about the house! We had 10 people in town for a wedding and her house was only 3 miles from the venue which was ideal! The house was clean and had nice little extra touches; the bottom floor was surprisingly spacious and perfect for hanging out! And the hot tub was a nice add also! Overall, it was a great experience!

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.

Nicholas and Dana's home was absolutely wonderful. Gorgeous sunrises and great accommodations. Tons to do to entertain family and friends. We never left and had a blast swimming, hot tubing, collecting shells, and playing games. Would love to stay again!

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.

Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

We spent some wonderful days in this house, it's spacious, beautiful and clean. We enjoyed the kayaks, paddle boards, jacuzzi, and the spectacular views of the river. Frank is an excellent host, very responsive. We definitely recommend this house for a relaxing and fun stay.

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 of 3 had an amazing vacation on our 4 day stay. It was so peaceful and relaxing. The place was exceptionally clean and organized with everything needed. Amazing views on the water and pool was great. We had some rainy weather but still managed enough dry time to enjoy the pool and outdoors

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.

I would definitely come back here. If you want to unwind, decompress, or just slow-living for a couple of days, you won’t find a better place. The sounds of small waves all day and the birds chirping in the morning were almost as good as the break-taking ocean view. Better than advertised. I could sit in the cabana and read all day.

We had an amazing stay at Ryan’s place for our Father’s Day weekend fishing trip! Ryuan was a fantastic host—very accommodating, responsive, and made sure we had everything we needed. The home was just what we hoped for and helped us create some wonderful memories. Thank you for making our trip extra special, Ryan! Would absolutely stay again.

This was our second year staying here and the place is perfect for our family. The layout and the ADA features were exactly as how they described them to be. This allowed my mother in law to be able to go out on the pier and enjoy her morning coffee. My daughter and I enjoyed the kayaks one morning. It was very relaxing and peaceful.

Cannot put into words how wonderful our time was at Away at the Bay! Just left my soon-to-be SILs bachelorette trip and the entire weekend was nothing short of incredible. Thank you so much to Ryan and Eric for creating such a wonderful experience in a place that truly feels like home but BETTER! Memories we will cherish forever.

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!

We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

We had a wonderful stay here! The location and setup was perfect for our multi generational family gathering. The level of detail and thought that was put into the amenities and setup was exceptional. The recommendations provided made planning our trip so easy. The kids (toddler to preteen) had a ton to do when the weather interrupted planned outdoor activities. The views were impressive. Marc was responsive when any questions came up. We all hope to return!