Cottage holiday rentals in Saint Michaels

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Popular amenities for cottage rentals in Saint Michaels

Cottage rentals with a hot tub

Superhost
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.
Top guest favourite
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
Cottage in Reedville
4.88 out of 5 average rating, 210 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

LorenRating, 5 stars1 week ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
Guest favourite
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.
Top guest favourite
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!
Guest favourite
Cottage in Annapolis
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.
Guest favourite
Cottage in Reedville
4.9 out of 5 average rating, 205 reviews

Bay cottage 🏖on the beach. Stunning views🏝

PaulRating, 5 stars2 weeks ago
We LOVED our stay! The screened porch overlooking the beach was so peaceful and our favorite place to be in the evening. The house was lovely, well cared for, very clean, and very tastefully decorated. The welcome book provided everything you needed to know about the house and surrounding area. We will be back again!
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

Pet-friendly cottage rentals

Superhost
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 favourite
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 favourite
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
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 favourite
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 favourite
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
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
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

Superhost
Cottage in Chestertown
4.91 out of 5 average rating, 35 reviews

Chesapeake East Shore Chestertown,Pool (May1),Dock

AntoinetteRating, 5 stars9 months ago
We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.
Guest favourite
Cottage in Lottsburg
4.98 out of 5 average rating, 87 reviews

Enchanting Edge of the World Cottage

JuliaRating, 5 stars1 month ago
Perfect Lake Side Vacation Spot!!! My friends and I spent the weekend and we absolutely loved it! The home is beautiful and the surroundings are so serine. Perfect place to get away and spend pleasurably days participating in outdoor activities like fishing, grilling and watching the sunset. We loved our stay so much we are already planning our next trip to the wonderful spot! Tim is an amazing host! Check in and check out were a breeze, he kindly checked in on us and was always prepared to help facilitate an enjoyable stay. I couldn’t recommend this listing any higher :)
Guest favourite
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 favourite
Cottage in Tall Timbers
5 out of 5 average rating, 46 reviews

Charming Waterfront Cottage with Sunset Views

CoryRating, 5 stars3 weeks ago
This house and these hosts represent the very best of Airbnb. I checked in on a beautiful Friday afternoon, but shortly after arrival, a storm hit the area that knocked out the power. Jenny and Dave were at the house to check on my welfare as soon as it was safe, despite a literal tree falling on their porch. I only live half an hour away, and could have easily gone home where there was still power, but decided to stay put where I was instead, and if that doesn’t tell you everything you need to know about how wonderful this house and location and hosts are, I don’t know what else to say. 10/10. I can’t wait to return for another staycation!
Top guest favourite
Cottage in East New Market
4.95 out of 5 average rating, 64 reviews

Cottage on Cabin Creek

MicheleRating, 5 stars1 month ago
It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.
Top guest favourite
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.
Guest favourite
Cottage in Saint Michaels
5 out of 5 average rating, 16 reviews

Lovely Cottage in St.Michael’s.Dock 7‘ Depth,Pet F

NicolaRating, 5 stars2 weeks ago
The massive legal agreement is a little intimidating (I’ve always taken care of my rentals) but basically everything was as described
Superhost
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

Destinations to explore