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Entire home

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

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

Fridge, microwave, oven, stovetop
Exterior detail
3 bedrooms, free WiFi, bed sheets
Property grounds
Exterior

Reviews

9.8 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 61280 sq ft

Popular amenities

  • Parking available
  • Kitchen
  • Dryer
  • Washer
  • Air conditioning

Add dates for prices

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 manager

Eastern Shore Vacation Rentals

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • 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

  • Smoke-free property

Location highlights

  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre

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

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Important information

You need to know

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 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
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.

Property is also known as

Vrbo Property
18

About the area

Map
St. Michaels, MD

What's nearby

  • St. Michaels Marina - 3 min walk - 0.2 miles
  • Chesapeake Bay Maritime Museum - 6 min walk - 0.4 miles
  • 1879 Hooper Straight Lighthouse - 6 min walk - 0.4 miles
  • St. Michaels Winery - 8 min walk - 0.4 miles
  • Saint Michaels Village - 3 min drive - 1.3 miles

Getting around

  • Cambridge Station - 33 min drive
  • Easton, MD (ESN-Easton - Newnam) - 20 min drive

Restaurants

  • ‪Foxy's - ‬4 min walk
  • ‪Chesapeake Landing Restaurant - ‬5 min drive
  • ‪The Blue Crab - ‬1 min walk
  • ‪Carpenter Street Saloon - ‬1 min walk
  • ‪The Crab Claw - ‬6 min walk

Frequently asked questions

Is Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife pet-friendly?

Yes, pets are allowed at this 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?

Situated in 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.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 35 out of 40 reviews
Rating 8 - Good. 4 out of 40 reviews
Rating 6 - Okay. 1 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.8/10

Cleanliness

Reviews

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

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

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

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

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

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

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

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

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

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

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

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

Carolyn E., Potomac, Md

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

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

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

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

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

10/10 Excellent

Julie G.

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

Easy, bright, airy, convenient and clean

We've stayed in St. Michaels many times by boat, but this was the first time we'd stayed in a house on shore and coordinated our visit with other family members arriving by boat. Having a home base (that welcomed our small dog!) was awesome, and the property was nicely equipped and welcoming. There were six of us and we were very comfortable and enjoyed the decor and the nice hardwood floors. We would absolutely stay there again. (If I had one heads-up for anyone, it would be to note that if you have a hard time with rooms that have a lot of light while you're sleeping, the upstairs queen bedroom (while lovely) has windows that are illuminated by a neighboring building's bright parking lot lights all night. The window coverings just couldn't compete! We covered the windows with dark towels and it really helped. I was glad I happened to have brought them with me.)
Stayed 4 nights in Jun 2022

10/10 Excellent

Jaci N.

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

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

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

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