
House vacation rentals in Saint Michaels
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Top-rated house rentals in Saint Michaels
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Popular amenities for Saint Michaels house rentals
House rentals with a pool

House in Edgewater Maryland
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!

Jul&Aug Avail | Waterfront+Beach+Pool | Gameroom
What a find! We were attending a wedding on the Potomac and found this gem of a place basically right next door. A perfectly appointed home in a peaceful, tranquil, beautiful setting. Connie was great! Responsive to our need to find the iron, not exactly an emergency, Connie responded immediately with it's location. Loved it!

The Glebe
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!

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

Punch Point boasts a sandy beach w/ pool and pier
Marissa’s place is always amazing. As usual, the house was very clean and equipped with everything a family with kids would need. We cooked multiple meals and had everything we needed in the fully stocked kitchen. The extra refrigerator upstairs came in handy for leftovers. The playroom and garage were packed with toys and games for kids of all ages. Marissa has truly thought of everything. Downtown St. Michael’s is only a short drive away and well worth the visit. We look forward to returning again soon!

Gorgeous, waterfront home - Perfect for Families.
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.

Large Home with Pool & 7 bedrooms; sleeps 21
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!

Beach Please! River cottage w/private beach & dock
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!
House rentals with free parking

Mid-Century Modern: Direct Private Beach Access
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!

Bay Breeze - 3BR Waterfront Chester River Retreat
This house was in a beautiful location. Everything was clean and comfortable, thoroughly enjoyed our stay. You cannot beat the views from the main level. Katie was communicative and we were even able to get an early check in!

Charming House, Quiet Neighborhood (Entire House)
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.

• Peaceful Point • A relaxing waterfront retreat
Peaceful Point was incredible and should be the standard that all other rentals follow. The home was well-stocked, organized and cozy, and I was blown away by the thought that went into preparations for guests. The furniture is well maintained and comfortable, the linens soft and clean, and the kitchen was filled with a variety of helpful items unlike the typical haphazard collection of damaged pots, pans and dishes--at Peaceful Point everything was of good quality and seemed to be purchased specifically for that home. The surrounding property was the epitome of peace and quiet, though activities like kayaking and paddleboarding kept everyone entertained. The local wildlife was plentiful and had us endlessly fascinated. Last but not least, our host Joanna was so helpful and proactive in her communications. She should teach a class on hospitality as she's clearly an expert! Thank you for such a wonderful stay, our family will cherish these memories always--hope to visit again soon!

Kent Island Escape
The place was wonderful. The house was clean. The beds were comfortable. The kitchen was more than well equipped. The setting was beautiful. The outdoors was perfect. Great outdoor furniture. The Bayview was unbelievable. The house in relationship to recreation is spot on. I can’t say enough great things about the place. I will definitely be booking again and again.

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

Downs By The River
We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!

Water Views in Rock Hall
Incredible, serene home with thoughtful design and furnishings. Our family loved the house, which served as a great space to gather over meals, games and stories. The deck on two sides of the house, with great seating, provided a gentle welcome to the nature around with harbor views in the distance. As seasoned Eastern Shore folks, this was an introduction to Rock Hall, which we really enjoyed, especially the refuge. Thanks, Lauren, for your insightful planning and attentive care for the house and your guests.
Weekly house rentals

Waterfront Annapolis Getaway!
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!)

River House on the Choptank
The house was perfect for us. We were in town for grandson's graduation and needed extra space and this definitely delivered. The property was amazing. Even though we couldn't physically enjoy much outside activities due to the rain we did get to enjoy beautiful views of the river from the large picture windows. Steven was always quick to respond to messages which was much appreciated!

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

Cozy 2BR Home near Idlewild Park
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!

Spacious waterfront home private pier dog-friendly
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!

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba
Very responsive host! Amazing home, felt brand new and very clean! Loved the loft area and great restaurants nearby!

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
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!

Ruby Of The Bay
Ruby on the bay lives up to its name. Such beautiful surroundings - loved being on the deck hearing the wind in the pines. I was grateful to unplug! Excellent size for my sister, me and our fur bosses. Could have comfortably fit 2 - 3 more adults. Nikki was instantly responsive & informative. I would love to return.
Quick stats about house rentals in Saint Michaels
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ661 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Nationals Park
- The White House
- Betterton Beach
- National Mall
- Georgetown University
- Hampden
- Oriole Park at Camden Yards
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- District Wharf
- M&T Bank Stadium
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- Patterson Park
- National Air and Space Museum
- National Harbor
- Smithsonian American Art Museum
- Meridian Hill Park
- Lincoln Park
- Crystal Beach Manor, Earleville, MD
- Maryland Renaissance Festival
- Killens Pond State Park