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

Saint Michaels, Maryland
$920 avg/night Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 4

Max Sleeps

Night 2 nights

Min Stay


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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Close To Skiing
  • PETS

    Pet Friendly
  • BEACH

    Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1200 Sq Ft (111 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Charcoal Grill Firepit Garden Outdoor Furniture Patio
  • POOL/SPA

    Outdoor Pool Private Pool
  • BATHROOMS

    2 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English Italian
  • THINGS TO DO

    Basketball Nearby Bicycle On Site Ecotours Nearby Golf Privileges Hunting Nearby Jet Skiing Nearby Kayak On Site Mountain Biking Nearby Power Boating Nearby Sailing Nearby Water Skiing Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Books DVD Player Games Music Library Stereo Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games Children's Toys Stair Gate
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near Outlet Shopping Near The Bay
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board Safe
  • SUITABILITY/ACCESSIBILITY

    1 Stairs To Reach Property Area Rugs In Public Areas Handrails In Stairways Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Note From Host: Owner Extremely Allergic Smoke-free Property Tile Flooring In Public Areas Upper Floors Accessible By Stairs Only

CheckIn Check-in : 03:30 PM CheckOut Check-out : 10:30 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Rates & Availability

Review Review

  • Christelle B.

    Submitted Oct 13, 2025

    Stayed Oct 10, 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!

  • Lisa P.

    Submitted Sep 20, 2025

    Stayed Sep 14, 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.

  • Kelly B.

    Submitted Aug 29, 2025

    Stayed Aug 24, 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.

  • Holly T.

    Submitted Aug 26, 2025

    Stayed Aug 11, 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!

  • Beth S.

    Submitted Aug 6, 2025

    Stayed Jul 27, 2025

    The house was cozy and clean. We loved the outdoor area with the pool. This property was close to everything so we didn't have to drive anywhere. The house was even better than described. Carol checked in midway through our week to see if we needed anything.We most definitely will come back again.

  • Rich C.

    Submitted Jul 28, 2025

    Stayed Jul 25, 2025

    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.

  • Chris A.

    Submitted Jul 28, 2025

    Stayed Jul 14, 2025

    Super Super...!!!!! Great Inn Keeper.. Nice Beds/ ..ect

  • Rebekah M.

    Submitted Jul 24, 2025

    Stayed Jul 17, 2025

    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!

  • Cynthia S.

    Submitted Jul 7, 2025

    Stayed Jul 4, 2025

    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.

  • Alyssa M.

    Submitted Jun 29, 2025

    Stayed Jun 15, 2025

    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!!

  • Paul P.

    Submitted May 21, 2025

    Stayed May 16, 2025

    I’ve stayed at this property 3 times. Same result every time. Great location, spotlessly clean, and excellent communication with Carol, the property manger. Strongly recommend.

  • Linda S.

    Submitted Jan 21, 2025

    Stayed Jan 18, 2025

    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.

  • Jennifer F.

    Submitted Dec 1, 2024

    Stayed Nov 27, 2024

    The property was beautiful, the home was well stocked and very comfortable.

  • Annie K.

    Submitted Oct 10, 2024

    Stayed Sep 27, 2024

    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!

  • Abigail D.

    Submitted Sep 26, 2024

    Stayed Sep 19, 2024

    Beautiful house, lovely accommodations, unbeatable location. Would return!

  • Pam D.

    Submitted Sep 9, 2024

    Stayed Sep 7, 2024

    We had a wonderful experience at the Harbor Hideaway. We will do this again for sure!

  • Michael D.

    Submitted Sep 5, 2024

    Stayed Jul 5, 2024

    This is a perfect property for a couples' weekend away. The house is clean, gives an accurate description and has amazing outdoor space. You could not ask for a better location for walking to restaurants, bike riding or just exploring the town.

  • John K.

    Submitted Sep 2, 2024

    Stayed Aug 29, 2024

    The description of the property is dead on. The house was spotless and Carol is by far and away exceptional to work with. They have thought of everything you could possibly need or want while staying here. The location is fantastic that you can just park and wall to everything you wish to do. The extras like kayaks, bikes, and all the toiletries you need make for a great stay. The beds were really comfortable and having sheets, towels and pool towels provided makes it so much easier. The pool was a refreshing addition on and you are located in a very quiet area so it’s very relaxing. We will 100% be returning for many future trips. If you are lucky enough to stay here it will instantly become your favorite go to cottage. Also, don’t worry the description is completely accurate as a matter of fact it really doesn’t do it justice. Enjoy your stay if you get to book here.

  • Kenneth C.

    Submitted Aug 24, 2024

    Stayed Aug 19, 2024

    Great place for a home base while exploring St. Michaels. The pool was a nice addition.

  • Colleen R.

    Submitted Jul 31, 2024

    Stayed May 22, 2024

    This property is so wonderful. Absolutely spotless and comfortable. The pool is fantastic and it has everything you need to enjoy St. Michaels!

  • Laura H.

    Submitted Jun 9, 2024

    Stayed May 17, 2024

    The house was exceptionally clean, comfortable and had everything we needed for our family of 4. We were in town for the running festival and the location was perfect. Carol provided detailed instructions about the property and check-in procedures. She was accessible every step of the way in planning our trip. We would definitely stay here again!

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Total

Includes taxes and fees
$920+
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