St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27

Photo gallery for St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27

A modern kitchen with white cabinets, stainless steel appliances, and a herringbone-patterned floor.
A house with a blue exterior, white windows, and a well-maintained garden with pink flowers and green shrubs.
A marina with boats docked, a wooden post in the foreground, and buildings in the background.
A kitchen with a sliding glass door leading to an outdoor patio with a pool and a covered table.
A backyard with a swimming pool, a patio with outdoor furniture, and a house with a blue exterior.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to St. Michaels Winery

Popular amenities

  • Patio
  • Private pool
  • Toys
  • Barbecue
  • Air-conditioning
  • Pet-friendly

Explore the area

View map
St. Michaels, MD
  • Place, St. Michaels Winery
    ‪3 min walk‬
  • Place, St. Michaels Marina
    ‪5 min walk‬
  • Place, Chesapeake Bay Maritime Museum
    ‪14 min walk‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪21 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Downstairs

1 Queen Bed

Upstairs

1 Queen Bed

2 bathrooms

Downstairs

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Upstairs

Soap · Towels provided · Bathtub · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden
Dining area

Add dates for prices

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About the area

St. Michaels

Located near the beach, this cottage is in Downtown St. Michaels, a neighbourhood in St. Michaels. St. Michaels Museum and Classic Motor Museum are cultural highlights, and some of the area's activities can be experienced at Windon Distilling and St. Michaels Winery. Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center are also worth visiting. Discover the area's water adventures with jet skiing and waterskiing nearby, or enjoy the great outdoors with hiking/biking trails and hunting.
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Map
St. Michaels, MD

What's nearby

  • St. Michaels Winery - 3 min walk - 0.3 km
  • St. Michaels Museum - 3 min walk - 0.3 km
  • St. Michaels Marina - 5 min walk - 0.4 km
  • Saint Michaels Town Hall - 11 min walk - 1.0 km
  • Chesapeake Bay Maritime Museum - 14 min walk - 1.2 km

Getting around

  • Cambridge Station - 33 min drive
  • Easton, MD (ESN-Easton - Newnam) - 20 min drive

Restaurants

  • ‪Foxy's Harbor Grille - ‬9 min walk
  • ‪The Crab Claw - ‬13 min walk
  • ‪Chesapeake Landing - ‬6 min drive
  • ‪Talbot St. Tavern - ‬8 min walk
  • ‪Purser's Pub - ‬18 min walk

Frequently asked questions

Does St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27 have a pool?

Yes, this property has an outdoor pool.

Is St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27 pet-friendly?

Yes, pets are allowed at this property.

How much is parking at St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27?

On-site parking is available at the property.

What time is check-in at St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27?

Check-in begins at 3:30 PM.

What time is check-out at St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27?

Checkout is at 10:30 AM.

Where is St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27 located?

Located in Downtown St. Michaels, this cottage is steps away from Windon Distilling, St. Michaels Museum and Classic Motor Museum. Saint Marys Square and Church Cove Park are also within 5 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 156 out of 157 reviews
Rating 8 - Good. 1 out of 157 reviews
Rating 6 - Okay. 0 out of 157 reviews
Rating 4 - Poor. 0 out of 157 reviews
Rating 2 - Terrible. 0 out of 157 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful in town cottage easy walk to everything. Private pool was a wonderful treat
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was located right in the heart of Saint Michaels and came exactly as described. Carol made the check in process seamless and left clear instructions for the house. It was perfect for a weekend getaway!
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our 2nd time renting from this property. It is such a great experience staying here both times. The house is very clean and comfortable and everything in town is within walking distance. Carol is so nice and easy to communicate with. We will definitely be coming back again! Thank you, Carol.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Equisitely appointed, kitchen fully equipped, furnished comfortably, modern, lovely reno, pool great addition, can walk anywhere easily
Stayed 7 nights in May 2026
Response from VrboOwner on 4 June 2026
Stephen and Patricia, You guys were wonderful guests. We loved having you!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I can't say enough about this property and how it both met and exceeded my expectations. The owner has thought of everything from tolietries; to the type of linens; to the right number of poolside towels. I have stayed at many rentals and this is at the top of my list. The proximity to the town is perfect. We definitely plan to book again the near future.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 12 August 2026
Monzella, Your sweet review means so much! Thank you!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fantastic stay at HH! This was our third visit to St. Michael’s, but first time renting & we will definitely be back! The house was beautifully clean and fully stocked with anything you could possible need. Location is great, walkable to all restaurants. Pool and backyard were so great- especially with a young baby and dog. Carol was so great as a host, great communication and so kind. Cannot wait to return!
Stayed 3 nights in Jun 2026
Response from VrboOwner on 12 August 2026
Danielle, We love that HH was part of some good times for your family. We loved having you as our guests.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful to have bikes and kayaks that are included with the house- you don’t see that often!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Thanksgiving Weekend Getaway Home Away from Home

The property was beautiful, the home was well stocked and very comfortable.
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely property, great location

Absolutely loved our stay at Harbor Hideaway. Every detail of the property is well thought out.
Stayed 5 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a visit to St. Michaels

Great place for a home base while exploring St. Michaels. The pool was a nice addition.
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely cottage

Great little cottage, perfectly situate near the town!
Stayed 2 nights in Aug 2019
Response from VrboOwner on 5 March 2020
Michael and family and friends , I’m so happy that you had a great time in Saint Michael’s, (my favorite small town in Maryland!), and that you enjoyed your stay at Harbor Hideaway. Providing a wonderful stay is our goal for all of our guests.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice weekend away

Owner was great. It's a great property
Stayed 2 nights in Jun 2020
Response from VrboOwner on 4 July 2020
Jeremy, I'm so happy that you guys ended up having a great stay even with my flub up. What Jeremy is being kind not to tell you is that all my family had just arrived for vacation and in all the excitement I forget to send him the instructions. I haven't ever done that but there is always a first and I so appreciate the patience that Jeremy and his family showed me as I got this to them. Thank you again for staying with us. Carol
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
beautiful property , terrific location only issues :upstairs bedroom slanted ceiling was difficult to navigate ducks droppings in and around pool convinced us to stay out of the water
Stayed 2 nights in May 2026
Response from VrboOwner on 4 June 2026
Rebecca, Thank you coming to stay with us at Harbor Hideaway. We appreciate your compliments about it's beauty and location. I'm sorry that you had trouble with ducks at the pool, but I can only help with things that guests make me aware of during their stays. I went back and read through all our messages on the VRBO thread and our mobile texts to see if I missed a message from you about any ducks. Your review is the first mention of them. We have a great team that works very hard to make your stay exceptional. We would have sent someone over to help rectify the problem if you'd let me know. Either way, we apologize. Carol Rum @ HH
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend getaway

This is a lovely home with all the amenities you would need. Super clean and well appointed. I recommend this property and host without reservation.
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

lovely getaway

Beautiful house, lovely accommodations, unbeatable location. Would return!
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was clean, comfortable, and convenient to town. Our favorite part was the pool. My grandson wanted to swim all day. We loved our stay. Thanks!
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday weekend

We had a wonderful experience at the Harbor Hideaway. We will do this again for sure!
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michael's Cute house

The house was very well equipped, in a great location and as cute as pictures and description described.
Stayed 3 nights in Mar 2021
Response from VrboOwner on 24 March 2021
MIchelle awoke to the sound of pool progress, meaning equipment noise making progress on the pool install on Monday morning and she still is kind enough to leave us a sweet review. We have to get that couple back when we can let them nap beside the pool! Michelle, your due for another visit once we are up and running. Truly, HH is and has been the best stay in SM's for years w/o a pool. Imagine how awesome it will be with one. Can't wait! Our summer calendar is filling up, reserve soon so that you can come enjoy a summer swim and afternoon nap at the new pool! Thank you Michelle for understanding our progress!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a perfect getaway from the city. From the beautifully appointed kitchen and bedroom, the sheets and towels, a gorgeous interior with a nautical vibe...to the swimming pool and backyard lawn, where we were able to relax and watch the clouds drift by. Going into town was simple, and the marina is very close if you walk and enjoy the boats on the river. Highly recommend the Harbor Hideaway for anyone desiring a peaceful visit to historic Saint Michael's.
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location is unbeatable; walking distance to all St. Michaels attractions. Home is decorated to perfection. We could not find anything missing or lacking. And the pool was a Godsend considering how hot it was.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfortable and Convenient

This was our second stay at Harbor Hideaway. We find it absolutely charming, and it's an easy walk to any of our favorite spots in town. It was thoughtfully outfitted with everything one would need, and is a comfortable home-base in beautiful St. Michael's. The pool is an extra bonus on a warm weekend.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a dream

This property is so wonderful. Absolutely spotless and comfortable. The pool is fantastic and it has everything you need to enjoy St. Michaels!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

The house was perfect - exactly as it looks in the listing- and the check out process was one of the best I’ve seen on VRBO (no need to take out trash etc.). Carol was extremely friendly and responsive and the pool is an added bonus! 5 stars from us!
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

The best house!

Choosing to stay at the Harbor Hideaway was an easy decision. Communication with carol was excellent and the house is beautiful! Extremely clean and you can tell they love/care about Harbor Hideaway and want you to have a great stay while you’re there! We will definitely be visiting again! Thanks for everything, Carol!!
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

AAAAA

Super Super...!!!!! Great Inn Keeper.. Nice Beds/ ..ect
Stayed 3 nights in Jul 2025
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