Cottage vacation rentals in Saint Michaels

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Popular amenities for Saint Michaels cottage rentals

Cottage rentals with a hot tub

Superhost
An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.
Cottage in Annapolis
4.86 out of 5 average rating, 81 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

MichelleRating, 5 stars2 weeks ago
Isaac was a great host! He responded very quickly any time we had an issue and the location and home was perfect for our stay! Overall 10/10.
Guest favorite
A hot tub is situated outdoors, surrounded by a gravel area. Water is seen bubbling inside, indicating a relaxing atmosphere. The hot tub is designed with a round shape and features built-in seating. Natural light creates soft reflections on the water's surface.
Cottage in Saint Leonard
4.96 out of 5 average rating, 135 reviews

Block to Beach, Screened deck, Hot Tub, No CF

BrookeRating, 5 stars1 month ago
My husband and I had a great stay at this cute little home. Everything was extremely clean and decorated to feel luxurious. We really enjoyed being so close to the water/beaches, 15 minute drive to shopping and the neighborhood was so quiet and peaceful. We took full advantage of the hot tub and it was our absolute favorite amenity offered, but we really loved the screened in porch as well. We would definitely come back to this area and consider staying here again! My only notes would be to add a few more pavers around the hot tub to make getting in and out in your bare feet more comfortable, and maybe a larger shower head to make rinsing long hair out easier. Overall, this trip was exactly what we were looking for to have a quiet get away for our anniversary and this place made it easy to do so!
Top guest favorite
A hot tub is situated outdoors with a view of the water and nearby pier. The setting sun reflects off the water's surface, creating a serene ambiance. Surrounding the hot tub are trees and space for outdoor seating.
Cottage in Woolford
5 out of 5 average rating, 62 reviews

Coral Cottage-w/Guest House-Waterfront-Hot Tub

MalgorzataRating, 5 stars2 months ago
A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.
Top guest favorite
A spacious outdoor deck is furnished with a sectional sofa arranged around a central table. Soft lighting from string lights enhances the atmosphere. In the corner, a hot tub is positioned, surrounded by nature and trees that create a serene backdrop.
Cottage in Lusby
5 out of 5 average rating, 11 reviews

Cozy Cottage close to Beaches & Solomon’s Island

JeffreyRating, 5 stars6 days ago
I have been doing airbnbs for over 5 years, this was the cleanest home ever, and The most comfortable beds I've ever slept in. And having a 12-year-old grandson who is very energetic, We love to play the Wii bowling and a few other of the Wii games. we got to watch some fun with us downstairs. The sauna was wonderful. these people are amazing in the house was amazing.
Superhost
An aerial view showcases a rustic-modern house surrounded by greenery. Red pathways lead to the entrance, and a wooden deck is visible with steps leading up to the front door. In the background, a private pool and shaded seating areas offer outdoor relaxation options.
Cottage in Marion Station
4.69 out of 5 average rating, 36 reviews

Year Round Playground - Rare Rustic-Modern Getaway

JaniceRating, 5 stars7 months ago
The house was very clean and very fresh smelling. Being in the woods surrounded by trees you can sometimes expect a musty smell, but that was not the case at all. The house was immaculate, and the rooms were very comfortable. The house was very quiet and private and the room was a nice touch. We all enjoyed the pool table. My husband did a lot of fishing at the dock and we also enjoyed the pool and the hot tub. We will definitely come back and stay at this house. Nadia was a great host. She mentioned that they are just starting out being a airbnb host, but you wouldn’t know it. The house had everything we needed.
Guest favorite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis
4.86 out of 5 average rating, 105 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

TiffanyRating, 5 stars3 months ago
In town for the Military Bowl and location was perfect. Loved the yard and would love to visit in the warmer months! Yarrow was excellent and had great recommendations! Highly recommend!
A private hot tub is surrounded by lush greenery, offering a serene outdoor retreat. The deck features a thatched umbrella and comfortable seating, creating an inviting space for relaxation among nature.
Cottage in Chesapeake Beach
4.5 out of 5 average rating, 20 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

BradleyRating, 5 stars15 months ago
Great stay and host was extremely kind and helpful.
Guest favorite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross
4.93 out of 5 average rating, 89 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

AdamRating, 5 stars1 week ago
This lake house was such a magical place. Being connected to nature, within the woods and by the lake, we enjoyed the serenity and quietness the entire trip. The house offers lots of space and comfort for a large group (we were 10). We took advantage of all the amenities including kayaking, watching a movie, lighting a fire outside, and the hot tub. No issues at all and hosts were super responsive and friendly!

Pet-friendly cottage rentals

Guest favorite
An outdoor space features a fire pit surrounded by several adirondack chairs in varying colors. The area is landscaped with a gravel surface and is bordered by a white picket fence, with flowering shrubbery and a small building visible in the background.
Cottage in Rock Hall
4.91 out of 5 average rating, 124 reviews

Cottage with Modern Updates - Walk to Waterfront!

LisaRating, 5 stars4 days ago
Absolutely Beautiful home!! Large yard. The Dog kids had a blast running after each other!! lol. Very spacious and loved the open floor plan and kitchen!! Outside fire pit what a plus!! Can’t wait to rent this again in the future!!!
Guest favorite
An outdoor terrace is adorned with brick pavers and surrounded by a rustic brick wall. A decorative iron gate leads to the garden, and a grill is positioned beside a seating area featuring a bench and planters with greenery.
Cottage in Annapolis
4.93 out of 5 average rating, 200 reviews

Secluded Cottage_ A+ Amenities in Historic Dwntwn

EricRating, 5 stars3 weeks ago
Jennifer's cottage is great! It is quiet, peaceful, and private but still right in the middle of everything - a 30 second walk to coffee shops, restaurants, bars, etc. Would also be really convenient for folks visiting the Naval Academy or St Johns. We had a great time and will almost certainly be back.
Guest favorite
A small, bright living area features a queen size Murphy bed and a single pull-out couch. A wooden coffee table sits between the seating and bed. Natural light floods the room through a large window, with sheer curtains gently framing the view.
Cottage in Glen Burnie
4.92 out of 5 average rating, 185 reviews

Home away from home

AmeliaRating, 5 stars1 week ago
A perfect little home away from home! My husband and I stayed here for 5 nights and felt extremely comfortable the whole time. The little touches (labeled guides, coffee options, guest book) created a warm and welcoming atmosphere, and we were very grateful for an experience that aligned exactly with what we expected. Thank you, Lena!
Superhost
Cottage in Lottsburg
4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

MichaelRating, 5 stars5 months ago
We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.
Guest favorite
A charming cottage is set on a spacious lawn, surrounded by lush greenery. The exterior features a wooden deck with steps leading to the entrance. A large tree provides shade, while a flagpole stands nearby, contributing to the serene atmosphere of the property.
Cottage in Kinsale
4.93 out of 5 average rating, 240 reviews

Great little cottage with a "Rivah" view

AlbinRating, 5 stars1 month ago
The place was just like in the pictures—very quiet and peaceful. Directions were clear and access was super easy. We especially enjoyed the kayaking—it was very good! We weren’t lucky enough to catch anything this time, but we still had a great time out on the water. The owner was also super accommodating and let us check out late without asking for any extra money, which was really kind and appreciated. Overall, it’s a nice and cozy spot, perfect for a relaxing getaway.
Superhost
Cottage in Tall Timbers
4.89 out of 5 average rating, 119 reviews

Old World Cottage/Fabulous Sunsets/Polite Pets OK

KarenRating, 5 stars1 month ago
A beautiful home with space for several people, close to the water and surrounded by beautiful pine trees. Clean and tidy with a coastal charm, pet friendly is an extra bonus! Owners were very supportive and communicative.
Superhost
Cottage in Port Republic
4.79 out of 5 average rating, 184 reviews

Shewell’s Cottage by the Shore

NoraRating, 5 stars1 week ago
What a gem of a place! So cute and cozy. A great location! Loved all the natural light that came in through the big windows. Everything was so clean yet very comfortable. Enjoyed walking the beach. Found sharks teeth and sea glass! Such a great surprise to find such treasures! Lisa was so very kind and accommodating. Appreciated the extras like coffee, bottled water, shampoo etc and she brought some wood for a cozy fire. They really worked hard at making our stay very comfortable. Definitely will be coming back. But plan on a longer stay because there is so much more in the area to check out!
Top guest favorite
A dining area is presented with a modern table surrounded by white chairs, offering a casual atmosphere. Natural light pours in through large windows. A beach-themed artwork depicting a tropical scene enhances the setting, while a coffee bar is conveniently located nearby.
Cottage in North Beach
4.98 out of 5 average rating, 148 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

JillRating, 5 stars3 days ago
Perfect location for a quiet, relaxing getaway. Everything about the stay was perfect and exactly as described/expected. We alternated between cooking in the AMAZING kitchen and eating at host recommended restaurants in North Beach. The house is located close enough to town if you choose to eat out (barely 5 minutes) and an acceptable drive to major grocery stores (15 minutes) if you opt to cook a few meals. The house was spotless. Hosts are super responsive and incredibly nice. Highly recommend staying at Bell Estates. Thank you, Daniel, for the perfect long weekend with my family!

Private cottage rentals

Top guest favorite
The exterior of the cottage is framed by two leafy trees, with a well-maintained front yard and a path leading to the entrance. The white facade features large windows, allowing natural light to brighten the interior. A welcoming sign is displayed near the front door.
Cottage in Colonial Beach
4.9 out of 5 average rating, 39 reviews

The Garden Cottage of Colonial Beach

BenRating, 5 stars9 months ago
This is our yearly spot to visit for our family beach trip, and it again did not disappoint. IMO this home provides one of the best values you will find, with a full kitchen, multiple bedrooms, and plenty of room to spread out. It is also walkable to the beach and restaurants, and the hosts treat us (and everyone) like family. Just book it and you won’t regret it!
Superhost
Cottage in Westover
4.87 out of 5 average rating, 69 reviews

Martha’s Cottage•at Old Beauchamp Homestead•

KendraRating, 5 stars5 months ago
It was a peaceful and quiet weekend getaway. The house was cozy and perfect for our trip. We can’t wait to come back and visit again.
Top guest favorite
A serene beach scene captures a tranquil twilight, with a silhouette of a wooden pier extending into calm waters. The sky displays soft hues of orange and blue, reflecting on the gently rippling surface, while sandy shores mask the transition from land to sea.
Cottage in Annapolis
4.93 out of 5 average rating, 28 reviews

Bay View Beach Cottage, perfect for long-term

MichaelRating, 5 stars3 months ago
The house was a perfect location on Cape St. Claire. Well furnished and comfortable. Susan is a great host.
Guest favorite
The image captures a serene view of the water, showcasing gentle waves lapping against a sandy beach. A clear blue sky stretches overhead, while distant land is visible along the horizon. The shoreline is marked by a pebbled beach, creating a tranquil setting.
Cottage in Earleville
5 out of 5 average rating, 10 reviews

Cottage at the bay We are pet friendly

RobertRating, 5 stars6 months ago
The stay was perfect for what we had going on at the time. The nights where beautiful and the venue was stocked full of anything needed for some out time cooking
Guest favorite
A bright sunroom features large windows that provide views of the surrounding greenery. Light, comfortable seating is arranged with decorative pillows. A coffee table displays a partial puzzle and small plants. Sunflowers in a vase add a touch of color to the scene.
Cottage in Easton
4.87 out of 5 average rating, 38 reviews

Loon Cottage on Leeds Creek

CorinnaRating, 5 stars1 month ago
We love staying here so so much! This is our second stay at Jennifer’s house and it was just as wonderful. Grateful our dog is allowed, comfortable beds, bright & warm… it’s a wonderful spot. I loved using the kitchen aid to bake cakes !!
Guest favorite
A serene waterfront deck is surrounded by lush greenery, featuring four lounge chairs and a table at the edge of Lake Lariat. The calm water reflects the trees, creating a peaceful outdoor setting suitable for relaxation and enjoying nature.
Cottage in Lusby
4.9 out of 5 average rating, 31 reviews

Elk Cottage-Lake Lariat / Private lake access

ShellyRating, 5 stars1 month ago
Britta's home was perfect for all of us! The kitchen had everything we needed and more. The home is spacious and in a quiet area with a beautiful view of the lake. The beds were super comfortable and everything was so clean! we look forward to staying again in the future! thank you Britta!
Top guest favorite
An aerial view showcases a serene waterfront cottage surrounded by lush greenery and open fields. Two private docks extend into the calm water, providing access for boating. The tranquil landscape includes a mix of trees and open space, with the expansive water body visible in the background.
Cottage in Rock Hall
5 out of 5 average rating, 79 reviews

Overton Farm Cottage

JanetRating, 5 stars5 months ago
My husband and I enjoyed another wonderful stay in Overton Cottage. Absolutely everything about this home is perfect for us, including the location, which gives us many opportunities for kayaking. We can walk to the Eastern Neck Wildlife Refuge, as well. The cottage itself is amazing and we always feel that we are slaying in the home of friends who have carefully chosen each decorative item, rather than a home that is clearly designed only for rental. We will be back!
Guest favorite
A serene outdoor seating area is set among tall trees, featuring a wooden deck and a round table with chairs. A few lounge chairs are positioned nearby, with a blue yoga ball resting on the ground. The cottage is visible, complementing the natural surroundings.
Cottage in Cambridge
4.98 out of 5 average rating, 87 reviews

Cambridge Cottage

CoryRating, 5 stars1 month ago
I absolutely adored this Airbnb! It was clean, adorable, and comfortable. I loved the aesthetic, but I will say if you have dogs, it would probably be safer to create them overnight. The spiral staircase was a bit difficult to maneuver for my larger guys. That’s not a problem at all, but just something to think about!

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