Carpenter Alley Cottage

106 Carpenter Alley
St. Michaels, MD 21663
Popular! Recently viewed by 146 other travelers!

- In-town St. Michaels cottage, newly renovated/furnished/appliances - Grill - Pet-friendly

Pets Welcome







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Newly Renovated Cottage in Center of Historic St. Michaels

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 Information & Notes:

  • Pet Policy: This property is dog-friendly for up to two dogs at no additional charge

  • Grill: This property has a propane grill. Propane is provided

  • WiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds, or access limited to email and web browsing and not streaming.

  • Linens/Starter Supplies: All ESVR properties include bed and bath linens, beds made prior to your arrival, and a starter supply of toilet paper, bathroom soap, paper towels, and dishwater detergent (but may not be enough for the duration of your stay). Please be sure to add these items to your grocery list.

Please Note:

  • This property does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

  • Weddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities shown above. Although they are deemed reliable, they cannot be guaranteed


  • Internet Service = WiFi
  • Microwave = Yes
  • Central A/C = Yes
  • Coffee Maker = Yes
  • Dishwasher = Yes
  • Toaster = 2 Slice
  • Stove = Yes
  • Washer = Yes
  • Dryer = Yes
  • Location = Village
  • Area = St. Michaels
  • Non-Smoking = Yes
  • Pets Allowed = Yes
  • Rental Type = Flex Stay
  • Total # of TVs = 2
  • Linens Provided = Yes
  • Last-Minute Deals = Yes
  • Oven = Yes
  • Heating = Yes
  • Towels = Yes
  • Dining Area = Yes
  • Smoke Detector = Yes

Ask us about Mini Week Availability!

Period Nightly Weekly
01/02/2021 - 04/30/2021 $250 $1700
05/01/2021 - 05/07/2021 $250 $1700
05/08/2021 - 05/14/2021 $250 $1700
05/15/2021 - 05/21/2021 $250 $1700
05/25/2021 - 12/31/2021 $250 $1700


Great location! Very clean and decorated nicely.
Great location! Very clean and decorated nicely. Gant and associates a local contractor restoration of the 120+ year old building is top-notch. The interior looks like a new building . Very professional, quick and easy reservation, check in and out.
Kurt G.
Dec 2019
This is a really nice property. The location is perfect, the house is super clean and the decor is simple and modern. I appreciate a house without clutter. The lighting in the house is especially thoughtful and we loved that there were fans and dimmers in each room. The bathroom (although small) were new and sparkling clean. Whoever designed and decorated the house did an amazing job. I could easily live there :). Beds were very comfortable. Everything was above our expectations. It's a wonderful place to stay for a trip to St. Michaels.
Nov 2019
A very nice house and location. I would definitely book the house again.
Oct 2019
We had a great stay in St Michael's. The house was really well appointed and had everything we need. It was in great condition and very clean. It was also an ideal location for exploring the town. Would definitely rent again in the future.
Sep 2019
We really enjoyed our stay at Carpenter Alley. The location is amazing - directly behind the main street and literally steps from all of the restaurants and shopping (including the Blue Crab for great coffee/breakfast). The house is clean, recently completely renovated with a nice layout, well decorated and has a fenced yard and grill for BBQing. We came with our dog and 11 month old son and had a really great stay! Would definitely come again.
Sep 2019
We had a great time, location can’t be beat!
Sep 2019
I live in DC and wanted to get away for a week. This was the perfect place to say! The house is located within walking distance to everything -- I didn't use my car once all week. The house was very clean and very nice! I cooked and grilled almost everyday, and the kitchen had pretty much everything I needed. You definitely get your money's worth when staying at this place! I will definitely be back and hope to make it my new summer destination spot.
Aug 2019
We had a wonderful weekend at Carpenter Alley! Three couples and a baby fit comfortably in the house, which was very clean and beautifully decorated. The location is perfect for walking to the bars, restaurants, and shops. We loved how close it was to the coffee shop and we enjoyed sitting outside on the patio at night. We would recommend this house to any groups planning a trip to St. Michaels.
Aug 2019
Great location - you can walk everywhere. Close to bars, restaurants, and the water.
Jul 2019
The communication with Vantage Vacation Rentals was very good. The house was very clean, updated, and close to the main street. It was a great place to stay and enjoy the local area.
Catherine Glatts
Jun 2019
We thoroughly enjoyed our stay at Carpenter Alley during our wedding weekend! The house was absolutely immaculate, beautifully decorated, and in a GREAT downtown location. If you’re looking for a clean, bright vacation house, this is it! It’s within walking distance to everything in downtown Saint Michaels. We hope to be able to return soon. - The Caws
Jun 2019
Amazing place, very conveniently located! Thanks!
May 2019
5k/half marathon finish line right beside the house. Started sound check for their microphone at 5:45am. Would have liked a heads up to bring earphones. If no race is going on, score 10. Very nice space, clean, updated house. Perfect for families, and close to many restaurants, and the downtown hub. Friendly, got information out to me in a timely manner.
Lindsay Silbernagel
May 2019
An absolute amazing experience
An absolute amazing experience from beginning to end. The house was sparkling clean, tastefully decorated and the beds were very comfortable.( the bunk room would work better with two twins or with a trundle). Perfect proximity to everything in St Michael’s. Definitely would rent in the future!!!! The staff was very easy to work with and answered all questions. Very friendly!!
Patricia K.
Apr 2019
The staff was extremely friendly, and accommodating. We were having work done to our house and they were very flexible with our arrival time, in addition to getting another night secured when we were told we could not return home when expected. The house is very clean, updated, open and airy. The back yard is spacious enough to play ball with dogs if needed. Its a half of a block away from the main street to all of the shops and restaurants. We loved it! Our stay was wonderful, very comfortable, and relaxing. It was perfect! The team was very friendly, and easy to work with. They were very accommodating, allowing us to secure an additional night at the last minute, and assisting us with an early arrival time. I really appreciate working with people like you, thanks so much for everything. Its good to be back in our home, but now I know who to call in the future when the need arises!
Skye Savageaux
Apr 2019
Lovely house and great location.
Pet-friendly is a super super plus Our stay was excellent! We were celebrating my 10 years of being cancer was an awesome location. House was decorated beautifully. Being Pet-Friendly meant we could bring our fur babies. I am so used to when renting is to vacuum up after ourselves and this house did not have a vacuum. With bring pets no matter if the do not get on furniture their hair flies around... I would have love to vacuum up after them :( but could not. sorry. The construction across the street did not hinder our enjoyment a bit. Thank you for letting us stay at your amazing home. - The Phillips Family Only had interactions via email....the email process was excellent and we received many email regarding the property for check in and check out process.
Pamela Phillips
Apr 2019
Outstanding renovations in this home, top to bottom, inside and out! Decor and furnishings are bright, clean, and tasteful. Really great job! This house in fifty feet off of the main road where the shops and restaurants are but has a nice little fenced in yard with a gas grill and a couple of chairs so you feel like you’re not in the business district. Three bedrooms, each with its own full bath, including one on the ground level for people who find stairs difficult. Nicely stocked kitchen for actual use, not just token yard sale coffee mugs. There is a comfortable sofa, occasional chairs with a television, and a table and chairs on each floor so you can have separate entertainment areas if desired. The upstairs sitting room has an assortment of board games. We were attending a wedding at the Inn at Perry Cabin. So close to the venue the valets would probably have dropped us off- but this Carpenter Alley rental gave us a nice quiet house to escape from relatives when we’d had enough.
Jan 2019
We loved the house and the location.
We loved the house and the location. Would definitely stay there again if the opportunity presented itself. Didn't really need to interact with the team too much, but the one question I had before arrival was answered promptly, accurately and courteously. All good.
David M.
Dec 2018
Property was great and we enjoyed our stay. Two notes - the dead bolt on the side door is very difficult to work, you all may need to give it some wd-40. Also, you may want to invest in a grill cover - with all the rain we've been having, we're concerned the grill will be rusted within a year without a cover.
Lindley Sherer
Aug 2018
Wonderful home.
Very responsive. Loved the location and the home!
Lori Price
Jul 2018

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