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

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Harbor Hideaway- Saint Michael's Premier In-Town Rental with a pool!
View from first floor bedroom which also opens to your bathroom.
Upper floor bathroom.
First floor bedroom with queen mattress.
Second work space is in upper area.

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4111.5 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

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

About this property

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


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

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 3:30 PM
Minimum age to rent: 25
Check out before 10:30 AM
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Children

Children allowed: ages 0–17
Stairway up to second floor is steep-caution
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Events

No events allowed
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Pets

Pets allowed
$150 Must declare or risk eviction-neighborwatch
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Smoking

Smoking is not permitted
Owner extremely allergic

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

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 Easton Cycle and Sport are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Cottages in St. MichaelsOpens in a new window
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
  • Chesapeake Bay Maritime Museum - 11 min walk - 1.0 km
  • 1879 Hooper Straight Lighthouse - 11 min walk - 1.0 km

Getting around

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

Restaurants

  • ‪Stars - ‬18 min walk
  • ‪The Crab Claw - ‬13 min walk
  • ‪Carpenter Street Saloon - ‬9 min walk
  • ‪Foxy's Harbor Grille - ‬9 min walk
  • ‪t at The General Store - ‬7 min drive

Frequently asked questions

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

Yes, this property has an outdoor pool.

How much does it cost to stay at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3?

As of 3 Apr 2026, prices found for a 1-night stay for 2 adults at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3 on 5 Apr 2026 start from AU$1,063, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

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 opens 4/3?

Check-in begins at 3:30 PM.

What time is check-out at St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3?

Checkout is at 10:30 AM.

Where is St. Michael's Premier In-Town Rental with heated pool. Pool opens 4/3 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. 146 out of 147 reviews
Rating 8 - Good. 1 out of 147 reviews
Rating 6 - Okay. 0 out of 147 reviews
Rating 4 - Poor. 0 out of 147 reviews
Rating 2 - Terrible. 0 out of 147 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jennifer F.

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

10/10 Excellent

Lisa P.

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

10/10 Excellent

Rebekah M.

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

10/10 Excellent

Kenneth C.

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

10/10 Excellent

Ashley B.

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

10/10 Excellent

Michael B.

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

Lovely cottage

Great little cottage, perfectly situate near the town!
Stayed 2 nights in Aug 2019
Verified

10/10 Excellent

Rich C.

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

10/10 Excellent

Jeremy R.

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
Verified

10/10 Excellent

Linda S.

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

10/10 Excellent

Cynthia S.

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

10/10 Excellent

Chris A.

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

AAAAA

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

10/10 Excellent

Alyssa M.

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

10/10 Excellent

Abigail D.

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

10/10 Excellent

Holly T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Beth S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Pam D.

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

10/10 Excellent

Christelle B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Michelle D.

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
Verified

10/10 Excellent

Annie K.

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

10/10 Excellent

Colleen R.

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

10/10 Excellent

Paul P.

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

Always exceptional

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.
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Michael D.

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

Great escape

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.
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Kelly B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Laura H.

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

Wonderful Weekend in St. Michaels

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!
Stayed 2 nights in May 2024
Verified

10/10 Excellent

Conor F.

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

Beautiful home, fantastic location

We had a wonderful time staying at Carol’s property! The bed was cozy, the kitchen was well stocked, and the pool was a perfect temperature. What makes this house special is it’s tucked in location but proximity to the Main Street of St. Michael’s and all it has to offer.
Stayed 3 nights in Sep 2023

About the host

Hosted by Carol Rum

Host profile image
Hi. I'm Carol. I am now the 'past' owner of HH. In 2020, HH was sold to new owners that are fantastic! They have added many new enjoyable amenities..... a beautiful new pool, new furnishings like desks, and HS internet services that make HH an easier place to come and do your remote work while enjoying Saint Michael's when you aren't working. I am now in the role of property manager. It's a beautiful transition for me because I still get to interact with those of you that inquire about a stay. I love meeting people which this job is a perfect fit for. My husband and I have traveled extensively, living for two years in Japan while teaching abroad and three in Italy. We now split our time between the US and Siena, Italy.
Though education was my calling for many years, I worked in design and had my own business related to that in my years in NC. With our move to MD, I wanted to follow my heart into the hospitality industry. Taking note of all the things that I enjoyed as we traveled and then incorporating them into my own summer rental has been very rewarding to me, and hopefully to the enjoyment of our guests. The ultimate goal for both myself as the past owner, and now for the new owners is to try to give our guests a great getaway that is made easy by the things that we provide. When I first bought this place in 2007, management companies made the guests pay extra for bedding and to have the beds already made up upon your arrival...who wants to do that on your getaway? Since 2007, HH set the path for many other rentals. We put in great mattresses, changed them out every three years, we dressed those mattresses with quality linens that are pressed and on the bed when you arrive. I'm proud to say we at HH lead the way in those small ways. That type of comfort and pampering brings many repeat guests year after year. I am so proud to say that HH's owner is just as committed to your comfort and the cleanliness of the cottage. Come see all our new beautiful updates!

Why they chose this property

The town of Saint Michael's has been one of my very favorite getaways from my very first vist back in the 90's. It felt like I was stepping back in time, safe and friendly. I love riding the bikes or walking around town, restaurants are great, shopping is fun, I feel like I'm back in my little hometown!

What makes this property unique

Our promise to our guests is that you will always find Harbor Hideaway to be extremely clean, fresh and comfortable. For this we can thank our long time cleaner Glenys. Our guests mention this fact over and over again in their reviews and as an owner I know that is over the top important to me when I look to stay somewhere. Our guests also love our location; so close to town and also only 4 houses from the water. When they aren't out exploring the town or their surroundings, they find it in enchanting to sit and relax in the rocking chairs on the front porch or enjoy the pool and the patio out back. Other visitors enjoying Saint Michael's pass by and there is always sweet banter going between guests about their stays. It just a lovely town and lovely neighborhood that we are fortunate enough to own and share a cottage in. I think you'll love it!

Languages:

English, Italian
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