Search Cottages in St. Michaels

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Browse Select St. Michaels Cottages

Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, 64 reviews
"Firefly cottage is a beautiful little place, super clean and with every possible convenience - well stocked, with lots of special touches. Terrific hosts and a lovely cottage - we thoroughly enjoyed it! Thank you…. Sheilah"
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, 23 reviews
"Wonderful hosts, great before and during stay communication, very friendly and welcoming. Cottage was cozy, well appointed and had the best view from the screened porch for morning coffees and evening glasses of wine!"
Cottage at Goose Neck Point
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, 189 reviews
"Beautiful grounds in a peaceful, isolated neighborhood. Absolutely as described in the listing. Hosts were helpful and responsive and absolutely everything we needed to enjoy the weekend was there."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, 6 reviews
"Great property, extremely clean and exactly as pictured on listing. Host was responsive and check in and check out was a breeze. Would recommend if you’re looking for a quiet weekend away at the Eastern shore!"
Eastern Shore Waterside Cottage Near St. Michaels
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, 24 reviews
"Appreciated the lovely waterfront location, independence , nice filtered water tap for drinking and coffee. Especially enjoyed meeting owner, delightful visit."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 199 reviews
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, 156 reviews
"Very nice home! It was decorated with many antiques and gave you a feeling of another time but with all the modern amenities for a wonderful time."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Waterfront property with private boat ramp and new dock!
10.0 out of 10, Exceptional, 2 reviews
"Fun stay in an older refurbished home. All of the amenities one could need with a great water front area"
Waterfront property with private boat ramp and new dock!
Waterfront home with beach mins to downtown boat or car Dog-Friendly
9.8 out of 10, Exceptional, 20 reviews
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
10.0 out of 10, Exceptional, 1 review
"We enjoyed our stay at Oyster Cottage! This historic dwelling, in a very walkable area of Rock Hall, is thoughtfully decorated with many artistic touches throughout the property. The upstairs beds and numerous downstairs seating arrangements are all very comfortable. The updated kitchen and ground-floor bathroom are well designed. We enjoyed sitting in a shaded area on the patio during the late afternoon. We had a relaxing visit and Diane is a very responsive property manager. Thanks for sharing...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, 90 reviews
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 128 reviews
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Artist, writer & creative minds stay where inspiration is free & serenity lives
Artist, writer & creative minds stay where inspiration is free & serenity lives
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, 19 reviews
"Thoroughly enjoyed staying at this cozy cottage It was very clean, had lots of towels, comfortable beds with soft fluffy bedspreads. We also enjoyed sitting outside on the screened in porch when we weren't in the hot tub. The fact that it was in a gated community with lots of gorgeous flowers and trees it felt very private."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, 1 review
"This was an amazing property. Very clean and very cute and cozy. Beautiful property. The owners were fantastic. Very responsive and caring. Loved it! Would definitely return."
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, 21 reviews
"Exactly as advertised Great location Recommend coded integrated keyless entry be installed - eliminate bulky current lock box entry process Excellent property - would stay again"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, 21 reviews
"Cute cottage, great location. Perfect for the 4 of us."
North Beach Cottage - Walk to Chesapeake Bay
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, 3 reviews
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
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See all available properties in St. Michaels
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

St. Michaels Cottages information

Number of reviews
998
Accommodation
70 Cottages
Lowest Price
Highest Price

St. Michaels Hotel Reviews
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