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

Holiday home in St. Michaels with kitchen

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

Living Area
Living Area
Kitchen
Living Area
Living Area

Reviews

9.8 out of 10
Exceptional
3 bedrooms3 bathroomsSleeps 6118.9 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View 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)
    ‪20 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 /

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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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

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
Property # 9391606

About the area

St. Michaels

Downtown St. Michaels, a neighbourhood in St. Michaels, is home to this holiday 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, power boating and sailing nearby, you'll find plenty of adventures in the water.
View more Holiday homes in St. MichaelsOpens in a new window
Map
St. Michaels, MD

What's nearby

  • Higgins Yacht Yard and Marina - 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
  • ‪Foxy's Harbor Grille - ‬4 min walk
  • ‪The Crab Claw - ‬6 min walk
  • ‪Carpenter Street Saloon - ‬1 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?

Yes, pets are allowed at this property.

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.
Learn moreOpens in a new window
Rating 10 - Excellent. 41 out of 46 reviews
Rating 8 - Good. 4 out of 46 reviews
Rating 6 - Okay. 1 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Cathy W.

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

10/10 Excellent

Jennifer E.

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

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

10/10 Excellent

Sydney S.

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

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

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

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

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

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

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

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

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

10/10 Excellent

Audra B.

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

10/10 Excellent

Scott B.

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.
Stayed 3 nights in Aug 2025

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

8/10 Good

Karen E.

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!
Stayed 3 nights in Oct 2024

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

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

10/10 Excellent

Mark C.

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

10/10 Excellent

Justin D.

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

10/10 Excellent

Amy B., Pineville USA

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

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

10/10 Excellent

Vicki P.

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

Great choice.

Loved the house. It was clean and pretty. Fabulous location.
Stayed 3 nights in Jun 2019

10/10 Excellent

Wes T., Annapolis, MD

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

Great location!

House was very clean, comfortable and well laid out. The location is fantastic! Perfect for being immersed in downtown Saint Michael’s. We’re able to walk to everything. Have the dog with us what a nice bonus.
Stayed 2 nights in May 2023

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

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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