St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3

Top rated by guests
Harbor Hideaway-  Saint Michael's Premier In-Town Rental with a pool!
Fully equipped kitchen - lovely large space to cook.
From kitchen looking out to pool.
Spring is here!
From the pool looking towards the house. Large outdoor area.
review stars
10Outstanding
(147 Ratings)
Guests raved about the exceptional cleanliness, comfort, amenities, and attentive host Carol. Perfect location for town exploring, running festival, and relaxing at the beautiful pool and backyard.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
10 / 10
Outstanding(147 Ratings)

Cottage in St Michaels, MD

4 guests · 2 bedrooms · 2 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 experienceA high end property in this area

About this cottage rental


As Saint Michael's Premier STR, we take this title very seriously, so read on to see what we've done this off season. Harbor Hideaway's in town location is just steps away from everything that St. Michael's has to offer. We've added a pool with a heater for guest stays in the spring and fall. The pool is quite large and the heater does help bring the water to around 80 degrees, but it can still feel cool is the temps are chilly. *Please understand before you book, the pool is only for our reserved guests staying at the cottage and never for pets.
The 1.5 story cottage was built in the 1940's. It was completely torn apart and remodeled in the the 90's. HH has been lucky with its owners. When owners actually use their property, (vs just as a rental investment) they care about it, and care FOR it. HH has been continually updated. Our current owners have beautiful designer taste, I call it Serena and Lily coastal....which makes it feel so good to spend time there. Our reviews often speak of our comfort and cleanliness, this remains a top priority for us. Again, this season, I fully expect many of our guests will speak of their love for the new coastal look! If you haven't seen our continued changes, it's time you booked! HH could be a photo shoot for S&L furnishings, it's that beautiful!
The off-season is always used to continue updates to HH. Besides the smaller things like new paint in and out; new windows, ceiling fans, and headboards in the bedrooms, mattresses, the bathrooms got a great new fabulous changes and the kitchen! A chef driven design with a stove you'll want to take home with you. New tile floors that look like whitewashed, patterned wood, new cabinets. We will continue to help you get the sleep that every getaway should offer with our new deluxe mattresses made up with resort quality, freshly pressed linens. We think you'll find this beautiful new look of the interior, in addition to the pool and patio, will make your stay feel like you just spent time at a high end resort. We hope all the updates please you, make you smile as you see them, and that they will make you want to come back time after time.
Harbor Hideaway is perfect for 1 to 2 couples, a girls' wknd, a small family, or anyone just in need of a relaxing getaway. HH is also set up for remote work with high speed internet for those looking for a multi-tasking getaway. Our guests have the best of the Eastern Shore living, with restaurants and shops in Saint Michaels, fresh crab from local watermen, delightful boat tours and skipjack rides, the nearby Chesapeake Bay Maritime Museum and abundant history and charm all around- all while staying in a quaint residential neighborhood.
HH guests also enjoy:
Kayaking through the harbor and out onto the Miles River or San Domingo Creek and following one of several kayaking pathways ( 2 boat ramps are near the cottage and available for easy entry) * HH has two kayaks for guest use. 1 single and 1 tandem plus life jackets.

Taking a ride about town on one of the 4 provided bikes.
Browse the Bookhound for your next read!
Tossing a game of cornhole
Watching the crab boats harvest the Bay's bounty
Taking a well-deserved nap on one of the two queen beds with new and comfy mattresses.
Enjoying one of the many in-town restaurants, or cook in HH's well-equipped kitchen or outdoor charcoal grill. When you don't want to cook- Simpatico now offers delicious meals to go.
Cracking crabs at one of the any restaurants or bringing them home to enjoy.
Taking an evening walk and stopping for ice cream.
Ending your evening by the firepit making s'mores.
Sipping coffee or cocktails poolside or on a rocker on the front porch while people watching.
Trying a craft beer and locally made spirits at the top of the street.
Going wine tasting a few blocks away- The Mill near Gina's (delicious margarita's)
Indulging in a cigar at the Old Mill (2 min walk)
Picking up nautical antiques and luxe home decor.
Indulging in a spa treatment (or two)
Try drinks at Fool's Lantern
Eastern Shore Brewery - The Gallery
208 Talbot- new management in 2024
Ruse. Corah's Corner for seafood
Simpatico
Lemoncello

Amenities at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3

Non-smoking
Pets allowed

Map of St Michaels, MD


Ratings and reviews

10 / 10
Outstanding(147 Ratings)
review starsSummary of reviews
Guests raved about the exceptional cleanliness, comfort, amenities, and attentive host Carol. Perfect location for town exploring, running festival, and relaxing at the beautiful pool and backyard.
From real guest reviews summarized by AI
10 / 10Outstanding·Oct 2025
We celebrated our daughter's and her husband 40th Birthday and decided to treat them to a week-end in St. Michaels. HH was the cutest, cozy and beautiful cottage located in the best part of town, close to the water, walking distances restaurants, shops and Rum Distillery! We enjoyed the vibe of house very much. The house was spotless! Carol was super responsive to all the questions I had and very flexible. We will definitely return for a getaway in the future... A Gem!
10 / 10Outstanding·Sep 2025
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.
10 / 10Outstanding·Aug 2025
This was our second stay at the cottage. We just love it here. So peaceful and relaxing. We enjoyed the pool and evenings around the fire. The fenced in yard is perfect for our family dog to enjoy. We love being able to park the car and walk to everything. We even enjoyed a bike ride. Perfect town to explore on bikes or just walking. The cottage is always so clean, cozy and inviting. Well stocked with quality items and everything you will need for your stay. Carol is a wonderful and attentive host and easy to communicate with. We look forward to our next stay.
10 / 10Outstanding·Aug 2025
Check-in and checkout was so simple and seamless. The entire house was immaculate and comfortable. Everything we needed was there and ready to go. The pool was amazing and the pool accessories were much appreciated. The neighborhood is so quiet and an easy walk to restaurants, stores, and even the bay. The yard was fully fenced and perfect for our dog. We’ll definitely be back!

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

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

Is St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3 pet friendly?

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

What amenities are available at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3?

We found 2 amenities for this rental. This includes non-smoking, and pets allowed.