Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife - Reviews, Photos & Rates

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Entire home

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Dates

December 2024

January 2025

Overview
Amenities
Policies
Location
Host

Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6119 sq m

Popular amenities

Barbecue grill

Pet-friendly

Parking available

Washer

Outdoor space

Kitchen

Explore the area

St. Michaels, MD

St. Michaels Museum
6 min walk
Limoncello Italian Restaurant & Wine Bar
1 min walk
Cambridge Station
33 min drive
Annapolis, MD (ANP-Lee)
75 min drive

Room options

Similar properties

Kitchen

Washer

Dryer

Pet-friendly

for 1 night

includes taxes & fees

5 Jan - 6 Jan

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

Recently renovated and newly furnished, 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!

During your stay at this vacation home, you're just a quick walk from St. Michaels Museum. The vacation home includes amenities such as free WiFi and a kitchen.

Air-conditioned home with kitchen, washing machine, and 3 bathrooms
Free WiFi
Onsite recreation includes a playground
Within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum

This vacation home offers its guests barbecue grills and a garden. The front desk is open around the clock.

Property manager

Eastern Shore Vacation Rentals

Property amenities

Internet

Free WiFi

Parking and transport

On-site parking

Kitchen

Fridge
Stovetop
Microwave
Oven
Dishwasher
Cookware/dishes/utensils
Coffee/tea maker
Toaster

Dining

Dining table

Bedrooms

3 bedrooms
Bed sheets provided

Bathrooms

3 bathrooms
Towels provided

Living spaces

Living room

Entertainment

Outdoor areas

Fenced garden
Barbecue
Garden

Laundry

Washing machine and dryer

Comfort

Air conditioning
Heating

Pets

Pet friendly

Suitability/Accessibility

Smoke-free property

Location highlights

Near a health or beauty spa
Near a hospital
Near outlet shopping
In a village

Things to do

Kayaking nearby
Fishing nearby
Wildlife and game walks nearby
Sailing nearby
Golf nearby
Power boating nearby
Winery tours nearby
Swimming nearby

Safety features

Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

Unit size: 1280 sq ft (119 sq m)

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 welcome
Service animals 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

Onsite parties or group events are strictly prohibited

Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip

Host has not indicated whether 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

You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

Property is also known as

Vrbo Property

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

9.8

Exceptional

9.8/10

Cleanliness

10/10 Excellent

Melanie H.

24 Nov 2024

Liked: Cleanliness

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

8/10 Good

Karen E.

11 Nov 2024

Liked: Cleanliness

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

8/10 Good

Andy S., Greensboro

22 Oct 2024

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

8/10 Good

Ferne D.

8 Oct 2024

Liked: Cleanliness

St. Michaels

Very clean, great location

Stayed 2 nights in Sep 2024

10/10 Excellent

Rennie M., Richmond, Virginia

9 Aug 2024

Liked: Cleanliness

Girls Trip

Perfect for a 3 day visit!

Stayed 3 nights in Jul 2024

10/10 Excellent

Tom O.

1 Jul 2024

Liked: Cleanliness

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

Karen L., Where do you live?Wilmington, DE

3 Jun 2024

Liked: Cleanliness

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.

26 May 2024

Liked: Cleanliness

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

Cathleen G.

28 Apr 2024

Liked: Cleanliness

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

10/10 Excellent

Sarah Z.

12 Nov 2023

Liked: Cleanliness

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

Amy B., Pineville USA

15 Oct 2023

Liked: Cleanliness

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

Carolyn E., Potomac, Md

9 Oct 2023

Liked: Cleanliness

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

Saum S.

14 Aug 2023

Liked: Cleanliness

St. Michael's

Amazing location in the middle of everything

Stayed 3 nights in Aug 2023

10/10 Excellent

Marta B.

4 Aug 2023

Liked: Cleanliness

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

Katie m.

21 May 2023

Liked: Cleanliness

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

14 May 2023

Liked: Cleanliness

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

Justin D.

16 Mar 2023

Liked: Cleanliness

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

Audra B.

2 Feb 2023

Liked: Cleanliness

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

Mark C.

2 Jan 2023

Liked: Cleanliness

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

David M.

16 Dec 2022

Liked: Cleanliness

Comfortable, clean and excellent location to walk around town.

Excellent

Stayed 2 nights in Dec 2022

10/10 Excellent

Dia S.

26 Nov 2022

Liked: Cleanliness

Very nice property, well located.

Property manager was helpful and very responsive. The property was very clean and tidy, but a bit sterile.

Stayed 3 nights in Nov 2022

10/10 Excellent

Cristina C., Ithaca, NY

21 Nov 2022

Liked: Cleanliness

Location, location, location!

This property is in the perfect location for getting around St Michael's, MD. Walking distance to all bars, restaurants, shops and shoreline. The check in process was simple and the house was clean and had all the amenities we could ask for. My only caviat is if you are a light sleeper, the weekend has a farmers market directly behind the home (seasonal) with acoustic music starting at 8am and on Friday and Saturday nights the Carpenter St Saloon has live bands until after 1am. We had a great stay and highly recommend it.

Stayed 2 nights in Nov 2022

10/10 Excellent

Joy L.

10 Oct 2022

Liked: Cleanliness

Perfection!

Everything about this stay was perfect! Location, property, and property manager was very attentive and helpful. Will definitely rent this property again!

Stayed 2 nights in Oct 2022

8/10 Good

Justin S.

18 Sept 2022

Liked: Cleanliness

Clean and great location, but surprising fees

My family stayed in St. Michael’s for the weekend and it was wonderful! The house was beautiful and the location was perfect— we were right in town, within walking distance to shops and restaurants. We would recommended staying in this location. However, be aware before booking that there are a lot of hidden fees. Our weekend trip total was doubled after fees.

Stayed 2 nights in Sep 2022

10/10 Excellent

Erica C.

15 Aug 2022

Liked: Cleanliness

St Michael’s perfection

This house is recently renovated and beautiful. The 3 bedrooms and 3 full baths along with 2 family rooms made the house live large. The location with a fenced yard and two off street parking spaces was ideal. Walkable to everything in St Michael’s including the bike/ped trail. We will be back!

Stayed 6 nights in Aug 2022