House vacation rentals in Saint Michaels

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Popular amenities for Saint Michaels house rentals

House rentals with a pool

Superhost
A serene swimming pool is featured in a private outdoor area, surrounded by a stone deck. Two white lounge chairs are positioned nearby, with trees providing a shaded atmosphere. The clear water glistens under a partly cloudy sky, inviting relaxation.
Home in Edgewater
4.91 out of 5 average rating, 146 reviews

House in Edgewater Maryland

TimothyRating, 5 stars3 weeks ago
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!
Guest favorite
A spacious bedroom features a large wooden bed with a light comforter and decorative pillows. Two leather benches are positioned at the foot of the bed. Natural light fills the room through large windows adorned with wooden shades, and a ceiling fan adds to the comfort.
Home in Montross
4.98 out of 5 average rating, 106 reviews

Jul&Aug Avail | Waterfront+Beach+Pool | Gameroom

DavidRating, 5 stars1 week ago
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!
Superhost
Home in Montross
4.92 out of 5 average rating, 207 reviews

The Glebe

KristinaRating, 5 stars2 weeks ago
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!
Superhost
A refreshing saltwater pool is framed by comfortable lounge chairs in vibrant red and blue. A large grassy area is visible beyond the pool, leading to serene waterfront views under a clear blue sky, complemented by a tree providing shade.
Home in Queenstown
4.81 out of 5 average rating, 157 reviews

Bay Breeze Retreat

TobyRating, 5 stars3 weeks ago
Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.
Guest favorite
An aerial view captures a spacious property surrounded by lush greenery. A rectangular pool is positioned in front of a two-story structure, along with multiple lounge chairs and a swing set nearby. The expansive lawn provides an open and inviting outdoor space.
Home in Sherwood
5 out of 5 average rating, 11 reviews

Punch Point boasts a sandy beach w/ pool and pier

ErickaRating, 5 stars1 week ago
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!
Guest favorite
The exterior view showcases a spacious backyard with an inviting swimming pool surrounded by lounge chairs and blue umbrellas. A two-story gray house stands prominently, with a deck and seating area visible, all framed by greenery and a clear sky.
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars2 weeks ago
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.
Guest favorite
The large in-ground pool is surrounded by a spacious patio, offering multiple lounge chairs for relaxation. A vibrant red umbrella provides shade in one corner, while lush greenery and flowering bushes frame the area, creating a private and serene outdoor atmosphere.
Home in Severn
4.88 out of 5 average rating, 170 reviews

Large Home with Pool & 7 bedrooms; sleeps 21

SamihahRating, 5 stars1 week ago
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!
Guest favorite
A scenic pathway lined with vibrant yellow flowers leads toward a charming cottage, nestled amid lush greenery. The cottage features a welcoming porch, surrounded by climbing vines, providing an inviting connection to the outdoor space and a view of the nearby water.
Home in Montross
4.99 out of 5 average rating, 155 reviews

Beach Please! River cottage w/private beach & dock

SarahRating, 5 stars1 week ago
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

Guest favorite
Two white Adirondack chairs are placed on a grassy area, facing a calm body of water. A sliver of rainbow is visible in the sky above the horizon. Lush greenery surrounds the scene, with a large tree providing shade.
Home in Chesapeake Beach
4.95 out of 5 average rating, 20 reviews

Mid-Century Modern: Direct Private Beach Access

LauraRating, 5 stars1 week ago
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!
Top guest favorite
A spacious living area is highlighted by a prominent stone fireplace, offering a cozy focal point. Two comfortable sofas are positioned around a light wood coffee table, which holds a decorative plant. Soft natural light fills the room from large windows, enhancing the welcoming ambiance.
Home in Grasonville
5 out of 5 average rating, 57 reviews

Bay Breeze - 3BR Waterfront Chester River Retreat

MollyRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious living area features a large sectional sofa with accent pillows, positioned around a glass coffee table. Light enters through multiple windows covered by sheer curtains. A contemporary kitchen is partially visible, with bar stools arranged at a kitchen island.
Home in Easton
5 out of 5 average rating, 12 reviews

Charming House, Quiet Neighborhood (Entire House)

DavidRating, 5 stars6 days ago
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.
Top guest favorite
A wooden pier extends over gentle waters, surrounded by rocks. The scene is illuminated by a soft pink and orange sky at sunset, reflecting on the water's surface. Additional pilings can be seen in the distance, enhancing the tranquil setting.
Home in Cambridge
5 out of 5 average rating, 33 reviews

• Peaceful Point • A relaxing waterfront retreat

KateRating, 5 stars2 weeks ago
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!
Superhost
Two black Adirondack chairs are positioned on a stone patio, facing a serene sunset over the bay. A small table with a decorative metal base is placed between the chairs. The silhouette of a tall tree is visible against the vibrant dusk sky.
Home in Chester
5 out of 5 average rating, 7 reviews

Kent Island Escape

CarolynRating, 5 stars1 month ago
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.
Top guest favorite
A large window fills the space with natural light, offering views of the tranquil waterfront and grassy area. A small desk and chair are positioned nearby, while outdoor seating is visible on a stone patio outside.
Home in Cambridge
4.98 out of 5 average rating, 52 reviews

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse

VictoriaRating, 5 stars6 days ago
One of the best places we have stayed! Nice and peaceful! We had the best time at Maria’s place.
Top guest favorite
A spacious room features large windows that provide views of the calm Patuxent River. A wooden table with several stools sits in the center, and a telescope is positioned beside the window, inviting observation of the serene landscape.
Home in Prince Frederick
5 out of 5 average rating, 15 reviews

Downs By The River

JeffRating, 5 stars6 days ago
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!
Top guest favorite
A modern living area features large windows offering expansive views of the surrounding greenery. A sectional sofa and a wooden coffee table are arranged on a patterned rug. Natural light floods the space, complemented by a television positioned on the wall.
Home in Rock Hall
5 out of 5 average rating, 39 reviews

Water Views in Rock Hall

JillRating, 5 stars5 days ago
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

Guest favorite
A serene waterfront view captures the calm South River, dotted with docks and boats. Lush trees frame the scene, adding to the tranquil setting. The sky is clear with a few clouds, enhancing the natural beauty of this peaceful retreat.
Home in Riva
4.88 out of 5 average rating, 34 reviews

Waterfront Annapolis Getaway!

NicholeRating, 5 stars2 days ago
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!)
Guest favorite
A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.
Home in Preston
4.95 out of 5 average rating, 98 reviews

River House on the Choptank

SandyRating, 5 stars2 weeks ago
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!
Guest favorite
A serene seating area is presented, featuring two plush pink chairs positioned on a decorative rug. A stylish chandelier adds soft lighting above. A fireplace mantel is adorned with a floral arrangement, and glass-paneled cabinets are visible in the background.
Home in Cambridge
4.86 out of 5 average rating, 63 reviews

High St. Art Gallery Suite

NadineRating, 5 stars1 month ago
My husband and I had a nice peaceful retreat from city life. Kristin’s cute place was just what we needed. Highly recommend!
Top guest favorite
An open living area features a spacious L-shape sofa in dark blue, complemented by a light-colored armchair. A coffee table with decorative items sits atop a large area rug. Natural light filters in, illuminating a neutral wall and showing a glimpse of the kitchen area in the background.
Home in Easton
5 out of 5 average rating, 16 reviews

Cozy 2BR Home near Idlewild Park

BethRating, 5 stars3 months ago
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!
Guest favorite
A scenic view showcases a well-maintained lawn leading to a private pier extending into Cox Creek. The landscape features lush greenery and vibrant flower beds, with a pathway that guides the eye towards the water, creating a serene outdoor environment.
Home in Chester
5 out of 5 average rating, 13 reviews

Spacious waterfront home private pier dog-friendly

DanRating, 5 stars1 month ago
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!
Superhost
The spacious living area features a warm wood ceiling and large windows overlooking the greenery outside. A comfortable sectional sofa and an accent chair are positioned around a rectangular coffee table, creating an inviting space. A modern fireplace stands elegantly against the wall, complemented by tasteful decor.
Home in Grasonville
4.75 out of 5 average rating, 4 reviews

Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba

MeghanRating, 5 stars2 weeks ago
Very responsive host! Amazing home, felt brand new and very clean! Loved the loft area and great restaurants nearby!
Top guest favorite
A tranquil view of the private pool framed by potted plants featuring colorful flowers. The pool area extends towards a serene body of water, surrounded by trees. The distant shore is visible, enhancing the natural beauty of the setting.
Home in Lusby
5 out of 5 average rating, 16 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

DeniseRating, 5 stars7 months ago
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!
Top guest favorite
A view of the Chesapeake Bay is showcased from a grassy area with two adirondack chairs positioned to face the water. A wooden pier extends into the bay, and the sky features soft blue and orange hues, reflecting the tranquility of the setting.
Home in Shady Side
4.96 out of 5 average rating, 25 reviews

Ruby Of The Bay

ReginaRating, 5 stars3 weeks ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Talbot County
  5. Saint Michaels
  6. House rentals