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

9.7 / 10.0

Outstanding(33 Ratings)

House in St Michaels, MD

6 guests · 3 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Top-tier experienceOne of the higher cost properties in the area

About this house rental

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!

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Dishwasher

Garden

Map of St Michaels, MD

Nearby attractions

Harriet Tubman Underground Railroad National Historical Park

37.5 mi

Navy-Marine Corps Memorial Stadium

33 mi

Lake Waterford Park

46.5 mi

Pirate Adventures on the Chesapeake

30.5 mi

$$$$

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

$$$$

9.7 / 10.0

Outstanding(33 Ratings)

House in St Michaels, MD

6 guests · 3 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Great for petsBring all your friends and family, even the furry ones

Top-tier experienceOne of the higher cost properties in the area

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Parking

Laundry

Dishwasher

Garden

Map of St Michaels, MD

Nearby attractions

Harriet Tubman Underground Railroad National Historical Park

37.5 mi

Navy-Marine Corps Memorial Stadium

33 mi

Lake Waterford Park

46.5 mi

Pirate Adventures on the Chesapeake

30.5 mi

Ratings and reviews

9.7 / 10.0

Outstanding(33 Ratings)

10.0 / 10.0

Aug 2024

Perfect for a 3 day visit!

10.0 / 10.0

Jul 2024

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.

10.0 / 10.0

Jun 2024

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!

10.0 / 10.0

May 2024

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.

10.0 / 10.0

Apr 2024

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!)

10.0 / 10.0

Nov 2023

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.

10.0 / 10.0

Oct 2023

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.

10.0 / 10.0

Oct 2023

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!

10.0 / 10.0

Aug 2023

Amazing location in the middle of everything

10.0 / 10.0

Aug 2023

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.

10.0 / 10.0

May 2023

The house was beautiful and location perfect. Would definitely stay again!

10.0 / 10.0

May 2023

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.

10.0 / 10.0

Mar 2023

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!

10.0 / 10.0

Feb 2023

This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s.

10.0 / 10.0

Jan 2023

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.

10.0 / 10.0

Dec 2022

Excellent

10.0 / 10.0

Nov 2022

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

10.0 / 10.0

Nov 2022

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.

10.0 / 10.0

Oct 2022

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

8.0 / 10.0

Sep 2022

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.

10.0 / 10.0

Aug 2022

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!

10.0 / 10.0

Jun 2022

Easy, bright, airy, convenient and clean

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.)

6.0 / 10.0

Jun 2022

Terrific Location & Nicely Decorated Home

Terrific Location & Nicely Decorated Home

We loved the location of this home (close to everything!) and the decor was very pretty. Listing needs to be updated to reflect lack of king sized bed and lack of real cable TV (only the three major channels are available). There were a few small maintenance repairs needed. The rental company probably would have fixed these if we'd reached out, but we were busy and didn't have time to deal with it. In general a very pretty house in a great location, but not a five star property in its current state. Note: The AC is just wall units downstairs and one works great, but the other is a bit weak (didn't blow much cold air - it was enough for my mother who is older and gets cold easily, but I wouldn't have survived in that room).

10.0 / 10.0

May 2022

Adorable cottage with large yard & garden.

Adorable cottage with large yard & garden.

This adorable cottage sits just off S. Talbot Street. Close to shops & restaurants. The cottage was extremely clean & tidy. Beautiful garden and yard. The upstairs common area was great for our family with its own living quarters and en-suite bedrooms.

10.0 / 10.0

May 2022

Fabulous for a girls’ weekend!

Fabulous for a girls’ weekend!

We had a blast and couldn’t have been happier at the cottage! Comfortable beds, clean, and PERFECT location.

10.0 / 10.0

Apr 2022

Perfect location!

Perfect location!

This place is exactly as described! The location is right in the center of town, so walkable distance to everything. The best part about this property is the fenced in yard. We were able to enjoy sitting outside with our dogs, without concern. The place is newly renovated and very clean. The sink faucet was the only annoyance. It works, but is not secured to the counter, so it moved every time you touched it. I’m sure that can be fixed super easy though. The beds were also very firm. Otherwise, we couldn’t have been more happy with this house, location, and stay! Thanks to the owners for sharing their home with us!

10.0 / 10.0

Jul 2021

St Michael s Charmer

St Michael s Charmer

This spotless beauty is in the perfect location to park your car for the weekend and walk everywhere you want.

10.0 / 10.0

Jun 2019

Great choice.

Great choice.

Loved the house. It was clean and pretty. Fabulous location.

10.0 / 10.0

Sep 2018

Fantastic location

Fantastic location

Very charming and nicely decorated with easy walking access to everything

FAQs

How much does this house cost compared to others in St Michaels?

The average price for a rental in St Michaels is $416 per night. This rental is $287 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

We found 9 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.

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Outstanding(612 Ratings)

St Michaels Harbour Inn, Marina and Spa

Inn

in Saint Michaels

1 king bed

Pool · Pets allowed · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Inn in St Michaels has everything you need for a rejuvenating stay. Treat yourself to St Michaels Harbour Inn, Marina and Spa's exceptional amenities, such as Air conditioner, Fireplace and Internet / Wifi.

$$$$

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

House in St Michaels, MD

Reasons to book

About this house rental

Amenities

Map of St Michaels, MD

Nearby attractions

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

House in St Michaels, MD

Reasons to book

About this house rental

Amenities

Map of St Michaels, MD

Nearby attractions

Ratings and reviews

FAQs

How much does this house cost compared to others in St Michaels?

Is parking included with this house?

Is there a pool at this house?

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

What amenities are available at Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife?

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