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

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December 2024
January 2025

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

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

Reviews

9.8 out of 10

Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 6119 sq m

Popular amenities

  • Barbecue grill
    Barbecue grill
  • Pet-friendly
    Pet-friendly
  • Washer
    Washer
  • Parking available
    Parking available
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen

Explore the area

Map
St. Michaels, MD
  • St. Michaels Museum
    6 min walk
  • Chesapeake Bay Maritime Museum
    6 min walk
  • St. Michaels Winery
    7 min walk
  • Annapolis, MD (ANP-Lee)
    75 min drive

Room options

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About the area

St. Michaels

In St. Michaels .Your stay at this St. Michaels vacation home places you within a 10-minute walk of St. Michaels Museum and Chesapeake Bay Maritime Museum. St. Michaels Winery is within half a mile (1 km) and Oxford Museum is within 9 miles (15 km).
View more Vacation homes in St. MichaelsOpens in a new window

What's nearby

  • St. Michaels Museum - 6 min walk - 0.6 km
  • Chesapeake Bay Maritime Museum - 6 min walk - 0.6 km
  • St. Michaels Winery - 7 min walk - 0.6 km
  • Avalon Theatre - 18 min drive - 16.9 km
  • U.S. Naval Academy - 72 min drive - 82.9 km

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
  • ‪Blue Crab Coffee Co. - ‬1 min walk
  • ‪Carpenter Street Saloon - ‬1 min walk
  • ‪The Crab Claw - ‬6 min walk

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!

Property manager

Eastern Shore Vacation Rentals

Property amenities

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bed sheets provided

Bathrooms

  • 3 bathrooms
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV

Outdoor areas

  • Fenced yard
  • Barbecue grill
  • 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

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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited.

Property is also known as

Vrbo Property
18

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 27 out of 32 reviews" "
Rating 8 - Good. 4 out of 32 reviews" "
Rating 6 - Okay. 1 out of 32 reviews" "
Rating 4 - Poor. 0 out of 32 reviews" "
Rating 2 - Terrible. 0 out of 32 reviews" "

9.8/10

Cleanliness

Reviews

8/10 Good

Karen E.

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

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.

Liked: Cleanliness
St. Michaels
Very clean, great location
Stayed 2 nights in Sep 2024

10/10 Excellent

Rennie M., Richmond, Virginia

Liked: Cleanliness
Girls Trip
Perfect for a 3 day visit!
Stayed 3 nights in Jul 2024

10/10 Excellent

Tom O.

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

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.

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.

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.

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

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

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.

Liked: Cleanliness
St. Michael's
Amazing location in the middle of everything
Stayed 3 nights in Aug 2023

10/10 Excellent

Marta B.

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.

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

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.

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.

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.

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.

Liked: Cleanliness
Comfortable, clean and excellent location to walk around town.
Excellent
Stayed 2 nights in Dec 2022

10/10 Excellent

Dia S.

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

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.

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.

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.

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

10/10 Excellent

Julie G.

Liked: Cleanliness
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