Title: Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife Vacation home in St. Michaels with kitchen ## Photo gallery for Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife ![TV - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/4d36e439.jpg?impolicy=resizecrop&rw=598&ra=fit) ![3 bedrooms, free WiFi, bed sheets - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c8f8b76.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/7c62e911.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/fb9a7f0a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)](https://images.trvl-media.com/lodging/49000000/48380000/48378600/48378570/38fa4ea8.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies In historic St. Michaels, Carpenter Alley Cottage offers the perfect blend of charm and modern conveniences. Enjoy nearby access to top-rated restaurants, boutiques, art galleries and waterfront activities like freshly caught steamed crabs along the Miles River. ## Reviews 9.8 Exceptional ### Entire home 3 bedrooms3 bathroomsSleeps 61280 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife Cottage in Center of Historic St. Michaels This lovely in-town cottage is close to all the amenities and charms of historic St. Michaels. Enjoy outstanding restaurants and boutiques, ice cream parlors, coffee shops, art galleries and more, all within a few steps of this beautiful home! Try the local winery, distillery, and brewery for tastings of hand-crafted spirits (no driving required!). Head toward the Miles River waterfront for freshly caught and steamed crabs. If you want to venture farther, within just a couple of blocks you can easily rent bikes, kayaks, or paddleboards and let your adventurous side soar. Offering modern conveniences in a quintessential Eastern Shore village, Carpenter Alley Cottage is a fabulous place to stay! PROPERTY FEATURES: Pet Policy: This is a pet friendly rental. Grill: Propane grill. Propane is provided. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds. BED SIZES: Bunk Bed - Single over Single - 1 / Queen - 1 / Queen - 1 / Queen - 1 / ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 3 bathrooms - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - TV ### Outdoor areas - Barbecue grill - Fenced yard - Garden ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### Location highlights - In a village - Near a health/beauty spa - Near a hospital - Near an outlet shopping mall ### Things to do - Fishing nearby - Golfing nearby - Kayaking nearby - Motor boating nearby - Sailing nearby - Swimming nearby - Wildlife walks nearby - Winery tours nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) ### General - Garden - Unit size: 1,280 square feet ## Similar properties ![Interior](https://images.trvl-media.com/lodging/58000000/57940000/57931900/57931801/c472e480.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Walk to Everything House Downtown St. Michaels - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 86 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=57931801&PinnedHotelID=57931801&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102290000/102284700/102284697/w2133h1598x0y2-359e012b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock St. Michaels - Pool - Hot tub - Kitchen - Washer 8.6 Excellent 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=102284697&PinnedHotelID=102284697&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115830000/115828500/115828458/74f94e98.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels Downtown St. Michaels - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 4 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=115828458&PinnedHotelID=115828458&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/83000000/82950000/82943900/82943888/b541b7f6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Modern Flat in the Heart of St. Michaels – Walk Everywhere Downtown St. Michaels - Kitchen - Washer - Dryer - Pet friendly 9.8 Exceptional 60 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-03&endDate=2026-02-04&selected=82943888&PinnedHotelID=82943888&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/33000000/32600000/32590200/32590170/7dc8015a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Location, Location, Location! 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You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as Vrbo Property 18 ## About the area Downtown St. Michaels, a neighborhood in St. Michaels, is home to this vacation home. St. Michaels Museum and Chesapeake Bay Maritime Museum are cultural highlights, and some of the area's attractions include Easton Cycle and Sport and Phillips Wharf Environmental Center. With kayaking, motor boating, and sailing nearby, you'll find plenty of adventures in the water. [Visit our St. Michaels travel guide](https://www.expedia.ca/St-Michaels.dx5940) [View more Vacation homes in St. Michaels](https://www.expedia.ca/St-Michaels-Private-Vacation-Homes.d5940-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C38.78559%2C-76.22467&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=eTf-buP4YGkvR5iO4vU88OSVDWk=) St. Michaels, MD ### What's nearby - Muskrat Park \- 2 min walk \- 0.2 km - St. Michaels Marina \- 3 min walk \- 0.3 km - Chesapeake Bay Maritime Museum \- 6 min walk \- 0.6 km - 1879 Hooper Straight Lighthouse \- 6 min walk \- 0.6 km - St. Michaels Winery \- 8 min walk \- 0.7 km ### Getting around - Cambridge Station - 33 min drive - Easton, MD (ESN-Easton - Newnam) - 20 min drive ### Restaurants - ‪Stars - ‬10 min walk - ‪The Crab Claw - ‬6 min walk - ‪Carpenter Street Saloon - ‬1 min walk - ‪Foxy's Harbor Grille - ‬4 min walk - ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬4 min walk ## Frequently asked questions ### Is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife pet-friendly? ### How much is parking? ### What time is check-in at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife? ### What time is check-out at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife? ### Where is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 42 8 - Good 4 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 9.8 Cleanliness ### 9.8 Location ## Reviews ### 10/10 Excellent #### Jennifer E. Sep 20, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Conveniently located! ##### Jennifer E. Stayed 3 nights in Aug 2025 ### 10/10 Excellent #### Jerome K. May 18, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Nice house perfectly located Good location, clean house, easy check in and check out process. ##### Jerome K. Stayed 2 nights in May 2025 ### 10/10 Excellent #### Lanise M. May 5, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great location and great house Property was perfect for our family stay. House was clean and well stocked. ##### Lanise M. Stayed 3 nights in Apr 2025 ### 10/10 Excellent #### Davinia W. Mar 24, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing location Great location with two parking spots and a small yard. Great for family vacation. ##### Davinia W. Stayed 2 nights in Mar 2025 ### 10/10 Excellent #### Cindi W. May 11, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Girls’ Weekend We had a wonderful weekend in St. Michaels and our stay at ur Carpenter Alley address was clean, nicely decorated, and the location was perfect for our group! ##### Cindi W. Stayed 2 nights in May 2025 ### 8/10 Good #### Ferne D. Oct 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### St. Michaels Very clean, great location ##### Ferne D. Stayed 2 nights in Sep 2024 ### 10/10 Excellent #### Karen L. Jun 3, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect place! 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! ##### Karen L. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Brett H. May 26, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect Location to Downtown St. Michael's 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. ##### Brett H. Stayed 2 nights in May 2024 ### 10/10 Excellent #### Saum S. Aug 14, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### St. Michael's Amazing location in the middle of everything ##### Saum S. Stayed 3 nights in Aug 2023 ### 10/10 Excellent #### Amy B., Pineville USA Oct 15, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect House This was the perfect house in the perfect location for our visit to St. Michael’s. The house was very clean and having a bedroom on the first floor was wonderful for our older guests. Hope to return. ##### Amy B. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Sarah Z. Nov 12, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Waterfowl We had a great stay at this property this year. Great location in town, and wonderful outdoor space for our dog as well. Very clean and ESVR provided all the items you need for the stay. Everyone had a good time for our long weekend stay for the Waterfowl festival. ##### Sarah Z. Stayed 3 nights in Nov 2023 ### 10/10 Excellent #### Tom O. Jul 1, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great central location in St Michaels Carpenter Alley was the perfect place for our group of family friends to explore St Michaels and the Eastern Shore. Right off the main street, an easy walk to all that St Michaels has to offer. Plenty of room for 6 adults with a great sized kitchen, upstairs and downstairs seating areas and fenced in back yard. Highly recommend. ##### Tom O. Stayed 3 nights in Jun 2024 ### 10/10 Excellent #### Carolyn E., Potomac, Md Oct 9, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### St Michaels My daughter and I come to St Michaels for long weekend get always…walk, eat, shop and rest. I e love the town and its history, the restaurant on the water and the museum! The house was perfect for us. Maybe install screens for cooler weather? But we enjoyed the property and ease to everything in town! ##### Carolyn E. Stayed 3 nights in Oct 2023 ### 10/10 Excellent #### Cathleen G. Apr 28, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing location! 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, older house so if you have people who are taller than 6'0 they might find themselves ducking to not hit the ceiling fan or doorways!) ##### Cathleen G. Stayed 2 nights in Apr 2024 ### 8/10 Good #### Andy S. Oct 22, 2024 Liked: Check-in, communication, location, listing accuracy #### Great Place - Location Excellent Other than arriving with no sheets on beds, no towels, and no basic toiletries or kitchen cleaning set, place is very good. Cleaning service, owner, or property management firm mismanaged the prep for our arrival. Absence of sheets, towels, etc. was rectified in a bit more than 1 hour. Nice place and superb location for seeing the village. Quiet, but right in the middle of all shops, farmers market, restaurants, etc. There was a bit of a pet odor in the 1st floor bedroom. Only other comment is that cost is a bit high once all fees added to base price. Would stay again, but price might make this prohibitive. ##### Andy S. Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Marta B. Aug 4, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Birthday Getaway We stayed at the Carpenter Ally Cottage for a quick escape to St. Michaels for a birthday celebration. It was such a lovely way to spend a few days before heading back to the busy life of work and school. The home was located perfectly in town. We walked everywhere. The home was comfortable and clean and felt as though we were staying with relatives. Well done! It's a great home for spending time historic St. Michaels. Limoncello is in your backyard and one of the best restaurants in town. There are coffee shops surrounding the home and antique shopping just down the street. The Village Shop was amazing for a "cook in" night. The water is just down the street and walk down at dusk after dinner was a perfect end to the day. We really enjoyed our stay and appreciate the efforts of the homeowners to make our stay comfortable. Check in and check out was easy as well. We highly recommend. ##### Marta B. Stayed 3 nights in Jul 2023 ### 10/10 Excellent #### Melanie H. Nov 24, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Unbeatable location Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway and the third easily parked in nearby public parking. The house is a little tricky to locate using GPS since the driveway is accessible through a public parking lot (look for Sprout Cafe & Bakery which is steps away). This is an older home and those who slept in the downstairs bedroom could hear those who slept upstairs when walking around, and the HVAC is loud. We still had a fantastic stay; however, these are a few things to be aware of when booking. The host was very responsive to questions and the home had everything we needed, including small packs of dish and laundry detergents and bathroom items. ##### Melanie H. Stayed 2 nights in Nov 2024 ### 10/10 Excellent #### Glen H. Sep 8, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Perfect location, everything as advertised. Highly recommend ##### Glen H. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Sydney S. Jun 15, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Wonderful home in excellent location!! ##### Sydney S. Stayed 7 nights in May 2025 ### 10/10 Excellent #### Josh M. Jun 16, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Very clean and modern house in excellent location in downtown St. Michael’s. Very comfortable and included convenient parking. ##### Josh M. Stayed 3 nights in Jun 2025 ### 10/10 Excellent #### Katie m. May 21, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect location The house was beautiful and location perfect. Would definitely stay again! ##### Katie m. Stayed 2 nights in May 2023 ### 10/10 Excellent #### Rennie M. Aug 9, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Girls Trip Perfect for a 3 day visit! ##### Rennie M. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Audra B. Feb 2, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Awesome girls weekend! This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s. ##### Audra B. Stayed 2 nights in Jan 2023 ### 8/10 Good #### Karen E. Nov 11, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Location, location, location We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time! ##### Karen E. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Scott B. Aug 18, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Location walking distance to everything, house well maintained, fenced back yard. The only thing that should be upgraded is upstairs air conditioning. We could not get inside temperature below 79 F on hot days. Maybe upsize capacity. Downstairs cooling was good. ##### Scott B. 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