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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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3 bedrooms, free WiFi, bed sheets - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
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Exterior - Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife (St. Michaels)
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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 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6119 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Add dates for prices

About this property

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

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets allowed

Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

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
View more Vacation Homes in St. Michaels
Map
St. Michaels, MD

What's nearby

  • Boats docked in the harbor, in St. Michaels, Maryland.
    St. Michaels Marina
    3 min walk - 0.3 km
  • Chesapeake Bay Maritime Museum
    Chesapeake Bay Maritime Museum
    6 min walk - 0.6 km
  • Saint Michaels Town Hall
    3 min walk - 0.3 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

  • Foxy's Harbor Grille
    4 min walk
  • The Crab Claw
    6 min walk
  • Chesapeake Landing
    5 min drive
  • Carroll's Market
    12 min drive
  • 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?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

Check-in begins at 4:00 PM.

What time is check-out at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

Check-out is at 10:00 AM.

Where is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife located?

Located in Downtown St. Michaels, this vacation home is steps from Higgins Yacht Yard and Marina and Muskrat Park. St. Michaels Marina and Saint Marys Square Museum are also within 10 minutes.

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Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 45 out of 51 reviews
Rating 8 - Good. 5 out of 51 reviews
Rating 6 - Okay. 1 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 0 out of 51 reviews

9.8

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Cathy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location
Stayed 2 nights in Dec 2025
Verified

10/10 Excellent

Jennifer E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Conveniently located!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Jerome K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice house perfectly located

Good location, clean house, easy check in and check out process.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Lanise M.

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.
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Davinia W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location

Great location with two parking spots and a small yard. Great for family vacation.
Stayed 2 nights in Mar 2025
Verified

10/10 Excellent

Sarah G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really liked this house and the location! The host was very responsive and helpful before, during, and after our stay. We had a minor issue with a backed up drain that they quickly resolved and they also promptly sent me back things we accidentally left behind. It was clean and comfortable. Loved the fenced in yard and gas grill. We already booked again for next year!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Cindi W.

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!
Stayed 2 nights in May 2025
Verified

8/10 Good

Ferne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michaels

Very clean, great location
Stayed 2 nights in Sep 2024
Verified

10/10 Excellent

Karen L.

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!
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Brett H.

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.
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Saum S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michael's

Amazing location in the middle of everything
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Amy B.

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.
Stayed 2 nights in Oct 2023
Verified

10/10 Excellent

Sarah Z.

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.
Stayed 3 nights in Nov 2023
Verified

10/10 Excellent

Tom O.

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.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Carolyn E.

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!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Cathleen G.

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!)
Stayed 2 nights in Apr 2024
Verified

8/10 Good

Andy S.

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.
Stayed 2 nights in Oct 2024
Verified

10/10 Excellent

Marta B.

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.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Melanie H.

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.
Stayed 2 nights in Nov 2024
Verified

10/10 Excellent

Sydney S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home in excellent location!!
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Alicia A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was in a perfect location. Loved having a fenced yard for my dog to roam. The bed was comfortable as was the sofas. I asked to extend my stay and they took care of everything. Having separate sitting areas would be great for larger families or groups.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Glen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, everything as advertised. Highly recommend
Stayed 3 nights in Sep 2025
Verified

10/10 Excellent

Josh M.

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.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Katie m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

The house was beautiful and location perfect. Would definitely stay again!
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Rennie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Girls Trip

Perfect for a 3 day visit!
Stayed 3 nights in Jul 2024