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Compare 70 Cottages in St. Michaels with updated reviews, rates, and availability.

Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (61)
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
Waterfront nature retreat, contemporary home w/ pier by Annapolis. Pet Friendly!
10.0 out of 10, Exceptional, (1)
Waterfront nature retreat, contemporary home w/ pier by Annapolis. Pet Friendly!
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
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Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (108)
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
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, (105)
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (152)
"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
Waterfront home with beach on the Chesapeake Dog-Friendly
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!"
Waterfront home with beach on the Chesapeake Dog-Friendly
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
Waterfront property with private boat ramp and new dock!
Waterfront property with private boat ramp and new dock!
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (22)
"My husband and I were looking for a place to getaway for the weekend, on the water. We found this adorable cottage, right on the water and close to Saint Michaels. We have been down to the area several times and really this was one of the best stays. The Hosts were really great, left us a bottle of wine and cheese plate when we arrived! the only thing that would have improved our stay would be if the bed was a little more comfortable. (by no means does this take away from the overall experience)...
Cottage at Goose Neck Point
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!
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (6)
"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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"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
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
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.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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, (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,
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
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (5)
"Lovely property, cool history beautiful decor"
Cozy, unique, historic registered cottage on the Corsica River!
MEMORIAL DAY SPECIAL - 3 DAY MINIMUM 10% OFF ROOM CHARGE
MEMORIAL DAY SPECIAL - 3 DAY MINIMUM 10% OFF ROOM CHARGE
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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

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (105)
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (108)
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (26)
"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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
881
Accommodation
70 Cottages
Lowest Price
Highest Price

Frequently asked questions

How much do cottages in St. Michaels cost?
Cottages in St. Michaels range between and per night. These properties offer a chance to soak up nature’s beauty — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in St. Michaels?
Reconnect with nature in one of the 70 cottages available in St. Michaels. To help you reserve an ideal property, make use of our handy filters to search for perks or amenities you need.
Why book your cottage in St. Michaels with Expedia?
We think a getaway should be a breeze, so if you’re in search of cottages in St. Michaels at an affordable rate, Expedia has got you covered. Keep the budget in check and opt for a wallet-friendly option far from the downtown buzz, or splurge on a luxury cottage to spoil your loved ones.
How can I find cheap cottages in St. Michaels?
With Expedia’s helpful filter tool, getting your hands on cheap cottages in St. Michaels is easy. To discover properties that’ll make your hip pocket happy, narrow down your search by amenities, star rating and budget.
What is there to do in St. Michaels near my cottage?
Whatever your interests, St. Michaels has a whole lot to keep you occupied. St. Michaels Winery, Avalon Theatre and St. Michaels Museum are on many visitors’ trip plans. You shouldn’t miss Academy Art Museum, Academy of the Arts and Historical Society of Talbot County either. With Expedia’s St. Michaels hotel deals, you can see even more fabulous attractions like these with the cash you save.

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