
Cottage vacation rentals in Saint Michaels
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Top-rated cottage rentals in Saint Michaels
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Popular amenities for Saint Michaels cottage rentals
Cottage rentals with a hot tub

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

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

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

Cozy Cottage close to Beaches & Solomon’s Island
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.

Year Round Playground - Rare Rustic-Modern Getaway
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.

Nautical Vibe Walk 2 Harbor Pubs USNA
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!

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Great stay and host was extremely kind and helpful.

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

Cottage with Modern Updates - Walk to Waterfront!
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!!!

Secluded Cottage_ A+ Amenities in Historic Dwntwn
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.

Home away from home
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!

Charming Waterfront Home with Expansive Views
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.

Great little cottage with a "Rivah" view
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.

Old World Cottage/Fabulous Sunsets/Polite Pets OK
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.

Shewell’s Cottage by the Shore
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!

Bell Estates-Brand New Bay View, Beautiful Cottage
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

The Garden Cottage of Colonial Beach
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!

Martha’s Cottage•at Old Beauchamp Homestead•
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.

Bay View Beach Cottage, perfect for long-term
The house was a perfect location on Cape St. Claire. Well furnished and comfortable. Susan is a great host.

Cottage at the bay We are pet friendly
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

Loon Cottage on Leeds Creek
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 !!

Elk Cottage-Lake Lariat / Private lake access
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!

Overton Farm Cottage
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!

Cambridge Cottage
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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