Entire home

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

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

A spacious living room with a sofa, ottoman, and two armchairs, a dining area with a table and chairs, and a kitchen with cabinets and a ceiling fan.
A two-story house with a front porch, a wooden fence, and a gravel driveway.
A white house with a wooden front door, a small porch, and a number '106' on the side.
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with patterned chairs.
A bedroom with a bed, a dresser, a vanity, a ceiling fan, and built-in shelves with various items.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • The great outdoors

    Guests love the outdoor space here.

  • Centrally-located

    You're never far from where you need to be with this convenient location.

  • Discover nearby landmarks

    Close to St. Michaels Winery
3 bedrooms3 bathroomsSleeps 6

Popular amenities

  • Barbecue grill
  • Air-conditioning
  • Pet-friendly
  • Washing machine
  • Refrigerator
  • Internet

Explore the area

View in a map
St. Michaels, MD
  • Place, St. Michaels Marina
    ‪3 min walk‬
  • Place, Chesapeake Bay Maritime Museum
    ‪6 min walk‬
  • Place, St. Michaels Winery
    ‪8 min walk‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪21 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Kitchen
Outdoor play area
Garden

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 /
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

Pets allowed

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 9391606
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

St. Michaels

Downtown St. Michaels, a neighbourhood in St. Michaels, is home to this holiday home. Higgins Yacht Yard and Marina and St. Michaels Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Muskrat Park. Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center are also worth visiting. With kayaking, power boating and sailing nearby, you'll find plenty of adventures in the water.
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Map
St. Michaels, MD

What's nearby

  • Saint Michaels Town Hall - 3 min walk - 0.3 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

  • ‪Foxy's Harbor Grille - ‬4 min walk
  • ‪The Crab Claw - ‬6 min walk
  • ‪Chesapeake Landing - ‬5 min drive
  • ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬4 min walk
  • ‪Talbot St. Tavern - ‬1 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 does it cost to stay at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

As of 20 Sept 2026, prices found for a 1-night stay for 2 adults at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife on 8 Nov 2026 start from £1,501, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

On-site 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?

Checkout is at 10:00 AM.

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

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

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 48 out of 55 reviews
Rating 8 - Good. 6 out of 55 reviews
Rating 6 - Okay. 1 out of 55 reviews
Rating 4 - Poor. 0 out of 55 reviews
Rating 2 - Terrible. 0 out of 55 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a great place to stay with family! Location was great. Walking distance to everything. The home was comfortable and spacious with 3 full bathrooms.
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and helpful team
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was in a super convenient place. There was plenty of parking. It fit all of our needs.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

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

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Overall, a great place for St Michal's shopping and Maritime Museum. The property is managed and the actual owner not really involved. We would strongly suggest a more reasonable "first day" arrival for those traveling a long distance... welcome basket of one day's supply of coffee, trail bar, chips, bottled waster, just anything to get travelers through the first few hours as there are no groceries in the downtown area. The management company does its best to work with what is there, but some upgrades to the actual property would be our suggestion(like hangers, a box of tissues, a grab bar in the tub/shower areas, etc)
Stayed 8 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our second time staying at this property! Still a good experience but a few things were broken (exhaust fan, shower door) which was disappointing and the property smelled a bit musty in some spots. The backyard is great for a dog which was the biggest draw and we love the central location!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 17 Aug 2023
Thank you so much for your review. We really enjoyed having you as a guest and for you helping to spread the word about our eastern shore vacation rentals. Our team looks forward to your next stay!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Girls Trip

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

10/10 Excellent

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.
Stayed 2 nights in Jan 2023
Verified review

8/10 Good

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

St. Michaels

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Bright space in a great location

If you you want to spend time walking around St. Michaels, this is the perfect spot, right in the middle of town. The three bedrooms are all comfortable, and the kitchen/living room is a nice place to hang out.
Stayed 5 nights in Dec 2022
Verified review

10/10 Excellent

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

St. Michael's

Amazing location in the middle of everything
Stayed 3 nights in Aug 2023
Response from VrboOwner on 28 Aug 2023
Thank you so much for this 5-star review and for helping to spread the word about Eastern Shore Vacation Rentals. We really enjoyed having you as a guest. Our team looks forward to your next stay!
Verified review

10/10 Excellent

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

Great House/Great Location!

Our family really enjoyed our time. The location of the house could not be better, just a few steps off of the main street! The house was very nice. Would definitely return!
Stayed 3 nights in Mar 2023

About the host

Hosted by Eastern Shore Vacation Rentals

Host profile image

What makes this property unique

3-BR, 3-BA, House, Sleeps 6, Grill, Fireplace, Close to Shops & Restaurants

Premier Host

They consistently provide great experiences for their guests

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