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
4.85 out of 5 average rating, 86 reviews

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

MichaelRating, 5 stars2 weeks ago
Nice house, very secluded, lots of entertaining space, hot tub was great, back patio, fire pit, everything was great. Isaac was very communicative with all aspects of our stay. An excellent getaway.
Superhost
A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.
Cottage in Woolford
5 out of 5 average rating, 64 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

TheresaRating, 5 stars4 days ago
Natalie was a wonderful host - the cottage was clean and welcoming and looked just like the photos. Natalie was very responsive, flexible and friendly. The river was peaceful and we enjoyed kayaking and fishing off the dock. We are very thankful we found such a perfect spot for our weekend trip to Maryland.
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
4.7 out of 5 average rating, 37 reviews

Year Round Playground - Rare Rustic-Modern Getaway

JaniceRating, 5 stars9 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.
Superhost
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, 15 reviews

Cozy Cottage close to Beaches & Solomon’s Island

LindaRating, 5 stars3 weeks ago
Emilio and Wanda’s home was absolutely lovely. They thought of everything to make our stay so enjoyable. Would recommend to anyone wanting a relaxing stay. So very close to Solomon’s Island. Thank you Emilio and Wanda!
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 Eastport
4.86 out of 5 average rating, 107 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

JohnRating, 5 stars4 weeks ago
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.
A furnished deck is surrounded by greenery, featuring a dining set under a large umbrella. Comfortable seating and a patterned area rug enhance the space, with details such as a small decorative lantern and a heating lamp visible.
Cottage in Chesapeake Beach
4.52 out of 5 average rating, 21 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

EstherRating, 5 stars1 month ago
I book this place for my bday I just wanted to have fun & have a break from routine but at the same time feel comfortable like home, and that’s how it was and better we all had a great time. Really nice property, fabulous decoration, great surroundings to visit, and nice backyard to relax and enjoy. The jacuzzi and fire pit unforgettable part of the trip, really nice atmosphere. If there was an issue super easy and efficient way to respond to the situation. Made my bday really special for me and my family <3
Superhost
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
4.94 out of 5 average rating, 93 reviews

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

MilotRating, 5 stars2 weeks ago
Genuinely one of the most pristine and peaceful places I’ve ever been at a great time, weather with family or friends
Superhost
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby
4.89 out of 5 average rating, 44 reviews

Hot Tub Hideaway by Shark Tooth Shores

RebeccaRating, 5 stars3 weeks ago
Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.

Pet-friendly cottage rentals

Superhost
The charming exterior of a historic cottage is depicted, featuring a welcoming front porch and an American flag. Lush green landscaping with flowers adds a touch of color, while a stone pathway leads to the entrance. The house is set against a backdrop of trees.
Cottage in Rock Hall
4.88 out of 5 average rating, 128 reviews

Cottage with Modern Updates - Walk to Waterfront!

SusanRating, 5 stars2 weeks ago
Great place in a cute area!
Guest favorite
Cottage in Deale
4.82 out of 5 average rating, 181 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

BobRating, 5 stars4 weeks ago
Shawn's place is great! It is well-cared for and has everything you need to enjoy the indoors and the outdoors. The views of the water are beautiful and you can spend a lot of time watching the different birds. Getting there is easy and not far from restaurants and grocery stores. Shawn makes you feel special and wants to ensure you have a wonderful stay. Hope to go back soon.
Guest favorite
The exterior of a single-story cottage is framed by lush greenery and mature trees. A white picket fence encloses the front yard, which features a small lawn and a decorative tree. Gravel pathways lead to the front entrance, with a shaded area beside the house.
Cottage in Deale
4.9 out of 5 average rating, 166 reviews

Rockhold Creek Cottage

ShamsRating, 5 stars1 month ago
We stayed at Richard's house for 3 nights in late Spring. Its an amazing place, with great views from the rooms. There were lots of great places to see nearby.
Superhost
The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.
Cottage in Glen Burnie
4.91 out of 5 average rating, 191 reviews

Home away from home

WalterRating, 5 stars3 weeks ago
a great little hideaway for your trip to the Baltimore and Anapolis area. a great host and comfortable place to stay!
Guest favorite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena
4.97 out of 5 average rating, 175 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars3 weeks ago
Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !
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
4.96 out of 5 average rating, 156 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

MichaellRating, 5 stars2 weeks ago
Great stay! The house was clean, cozy, and had everything we needed. Daniel was a fantastic host, very friendly and responsive. Highly recommend!
Superhost
A quaint yellow cottage is framed by a wooden fence and natural greenery. The front porch features colorful doors and multiple windows, allowing ample light to enter. A deck extends from the house, providing a welcoming space for relaxation amidst the surrounding trees.
Cottage in Port Republic
4.79 out of 5 average rating, 185 reviews

Shewell’s Cottage by the Shore

NoraRating, 5 stars2 months 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!
Superhost
Two individuals are seated at small red tables overlooking the waterfront. Each holds a glass of red wine. A firepit with firewood is positioned between them, with a scenic view of the water and trees in the background.
Cottage in Kinsale
4.93 out of 5 average rating, 112 reviews

Peaceful Waterfront 3 BR/2BA

LaurieRating, 5 stars3 weeks ago
Beautiful, peaceful place to stay! The host was friendly and very responsive when communicating! This cottage was exactly as the pictures show and the description given! I would recommend Parker’s Creek Cottage to anyone looking to stay in beautiful Kinsale!

Private cottage rentals

Guest favorite
Cottage in Heathsville
4.87 out of 5 average rating, 113 reviews

Cottage with a view!

GraceRating, 5 stars2 weeks ago
Beautiful place to stay. Quite peaceful area with friendly neighbors. Home was cozy and welcoming. Kitchen had everything you could need. Amenities were amazing. Had a spectacular time would definitely come back to stay again.
Guest favorite
A tranquil waterfront scene showcases a private dock extending over calm waters. Lush grasses border the shore, with a clear blue sky above. The textured rope leading to the dock adds an element of interest, inviting relaxation and reflection in this serene natural setting.
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 months ago
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!
Top guest favorite
The waterfront cottage is displayed amidst lush greenery, featuring a large wrap-around porch and steps leading down to the water. Outdoor seating areas and kayaks are visible on the dock, with a serene view of the cove reflecting the surrounding foliage.
Cottage in Lusby
4.98 out of 5 average rating, 63 reviews

Amazing, Secluded Luxury waterfront cottage!

AmyRating, 5 stars1 month ago
Beautiful place! My family loved it there. Perfect staycation. Lots to do just at the house! KJ was a great host.
Top guest favorite
An illustrated children's book titled 'The Little Blue Cottage' is positioned on a rustic wooden table. The cover features a scenic coastal scene, with a small blue cottage, sailboats, and various elements of nature, capturing a whimsical charm ideal for families.
Cottage in Hollywood
5 out of 5 average rating, 38 reviews

The Little Blue Cottage

MaryRating, 5 stars3 months ago
The Little Blue Cottage was comfortable and clean! Krista was extremely flexible with the check in and check out procedures.
Superhost
Cottage in Lottsburg
4.9 out of 5 average rating, 102 reviews

Charming Waterfront Home with Expansive Views

MichaelRating, 5 stars6 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.
Top guest favorite
A vibrant green kayak rests on a sandy beach, partially in shallow water. The calm river reflects the clear blue sky, with a wooden dock visible in the background. Sunlight illuminates the scene, creating a serene and inviting setting for water activities.
Cottage in Leonardtown
4.96 out of 5 average rating, 93 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

AnaRating, 5 stars3 weeks ago
Lovely place to disconnect from your day to day life.
Top guest favorite
The renovated cottage features a white exterior with blue accents, surrounded by lush greenery. A small porch with a light blue railing leads to the entrance. A brick pathway and outdoor seating area are visible in the well-maintained yard.
Cottage in Annapolis
4.98 out of 5 average rating, 47 reviews

Charming Waterfront Cottage on Historic Property

LizRating, 5 stars1 month ago
What an absolute treat to stay at the Cottage at Whitehall. We had such a lovely time, we stayed an extra day! Ty & Susie are gracious hosts and we were so excited to get a tour of the mansion and explore the grounds. The private beach at the back of the cottage is phenomenal, please take the canoe out - or even go for a swim. The sand is silky and soft, it was like a giant swimming pool nearly all to yourself. My husband enjoyed the canoe immensely (the waves scare me, so it wasn’t too much for me / but if you canoe out on the Meredith River it’s much calmer). If you fish - bring your fishing gear!! (Check local laws first, of course) Absolutely do not hesitate to book here if you have the chance, highly recommended 😍
Superhost
A serene waterfront view is captured at sunset, featuring silhouettes of Adirondack chairs arranged along the edge of the water. Gentle ripples reflect the warm orange and pink hues of the sky, while trees frame the scene in the background, creating a calming atmosphere.
Cottage in Saint Michaels
4.78 out of 5 average rating, 27 reviews

Cottage #1 Lighthouse First Cottage down driveway

GrayRating, 5 stars2 weeks ago
We had such a wonderful time staying at this airbnb! My partner and I can for a relaxing weekend away and this place definitely delivered! the cottage was adorable and just as pictured, and the location was perfect! we spent much of our time in the lovely shared yard space, watching the sunset, barbecuing, and sitting by the fire, and we took out a canoe for hours on the water - such a nice perk that these were provided! the hosts were so welcoming and always eager to help! I would love to come stay again

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