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Browse Select St. Michaels Cottages

Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (59)
"The Firefly Cottage is a charming cottage ideally located in the community of St Cape Claire. Restaurants are close by and we highly recommend the Breakneck Grill. The cottage is well equipped and appointed. The backyard has has a hot tub and beautiful wild flower garden. Within walking distance is a park and beach area. We had a great time and found the location ideal to get to all the wedding festivities around Annapolis. Patricia is a terrific host and thinks of all the little things that...
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (65)
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
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Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
3 bedrooms, desk, iron/ironing board, free WiFi
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (20)
"Beautiful house in peaceful West Annapolis, a short distance from the local shops and restaurants and the Naval College. Well equipped, everything you need, a real home from home and a very friendly, helpful and accommodating host. Highly recommended place to stay!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Sun loungers, beach towels
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (20)
"We have been VRBO'ing for quite a few years now and have had lots of positive experiences - but THIS property goes beyond all expectations in ways others can't. I can't think of another property layout that could offer what this one does - soothing water in every direction (where else can you see sunrise AND sunset over water?) and the large screened in porch with a view of the water was so comfortable and relaxing that we had to talk ourselves into leaving to go anywhere! The host could not...
Cottage at Goose Neck Point
Interior
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (20)
"We highly recommend Maria’s beautiful Beach cottage! House was fully equipped, beds were amazing, a lot of space and games galore! Thank you for contacting me prior to our stay with your contact information- made me feel welcomed and secure prior to our arrival. We will definitely be back when the weather gets warmer☀️🌈"
North Beach Cottage - Walk to Chesapeake Bay
Property grounds
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
10.0 out of 10, Exceptional, (48)
"The property was very clean and well decorated. You could tell care and love is placed into the house and landscaping. The backyard and pool area is gorgeous! Despite unlucky/rainy weather and temperatures in the 60s, the pool was heated so warm that we went in everyday with the kids which was so nice. Annapolis is very close by. Plenty of fluffy towels, comfortable beds, nice small touches of welcome goodies and quality soap/shampoo, etc."
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Exterior
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (4)
"Very nice property. Enjoy the weekend. Would recommend to anyone visiting the Chestertown and Centreville area."
Cozy, unique, historic registered cottage on the Corsica River!
Sun loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (89)
"Lovely visit. I have a 1 and 3 year old. They loved the water and meeting the llama. The room set up is confusing in the listing. Its 3 bedrooms with 2person beds and a forth bedroom w a 1person bed."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (1)
"Thank you so much for our wonderful time at the Point of View. We were so comfortable we didn’t want to ever leave – it was clean and comfortable. The home feels brand new because it has been renovated very recently. The furniture and kitchen are brand new and perfect for the space. The water views are incredible in every direction – we watched stunning sunrises (and moon rises!) to the east, we watched the awesome sunsets to the west and thoroughly enjoyed watching all the action in Dogwood...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Fridge, microwave, stovetop, dishwasher
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (8)
"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."
Updated North Beach Cottage: Pet Friendly!
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (195)
"We enjoyed our stay very much. It was lovely to sit either on the screened in porch or in the living room and look out onto the water. It happened to be chilly & rainy during our stay but with views of the water, we didn’t even mind that."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (85)
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (17)
"This was the perfect space for our family of five. Check-in was a breeze and Isaac even went as far as to leave the lights on for us knowing we were getting in late. Isaac let us know he was available if we needed anything, but we did not. Despite the rain, we were able to enjoy the hot tub overlooking the creek. The view was stunning! If you are looking for a peaceful stay, this is it!"
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
View from property
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (22)
"Emwe enjoyed our time here, it was relaxing and close to travel around the area."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Property grounds
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
9.8 out of 10, Exceptional, (20)
"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!"
Still Available for 2024 Commissioning Week! Dog-friendly beachfront home on the Chesapeake
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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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

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is CA $856
CA $1,927 total
includes taxes & fees
Jun 4 - Jun 5
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - 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
1,240
Accommodation
61 Cottages
Lowest Price
Highest Price

Recent Reviews in St. Michaels
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