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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 modern kitchen with white cabinets, stainless steel appliances, and a dining area with patterned chairs.
A white house with a wooden front door, a small porch, and a number '106' on the side.
A two-story house with a front porch, a wooden fence, and a gravel driveway.
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

  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

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

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.
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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
  • ‪Chesapeake Landing - ‬5 min drive
  • ‪Rise Up Coffee - ‬4 min drive
  • ‪Blue Heron Coffee - ‬5 min walk
  • ‪The Blue Crab - ‬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 23 Aug 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 £1,472, 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.

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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