St. Michael's Premier In-Town Rental with heated pool. | Cottage in St. Michaels

10.0 (145 Reviews) |   Pet Friendly   2 Bedrooms  2 Bathrooms  4 Guests
St. Michaels Cottage | St. Michael's Premier In-Town Rental with heated pool.

2 Bedroom Cottage in St. Michaels

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. 2021-we added a pool with a heater for guest stays in the spring and fall. *Please understand before you book, the pool is only for our reserved guests staying at the cottage.
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

St Michael's Premier In-Town Rental with heated pool is located in St. Michaels. St Michael's Premier In-Town Rental with heated pool provides accommodation, featuring Air Conditioner, Guest Services, Child Friendly, among other amenities. This Cottage features Air Conditioner, Guest Services, Child Friendly, to make your stay a comfortable one.

St Michael's Premier In-Town Rental with heated pool has 2 Bedrooms , 2 Bathrooms, and max occupancy of 4 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the St. Michaels has interesting places to visit. If you want to learn more about the Cottage in St. Michaels, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pet Friendly
Pool
TV
View
Private Pool
Ocean View
Balcony/Terrace
Oceanfront
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Air conditioning
  • Heating
Bathrooms
  • Toilet paper
  • 2 bathrooms
  • Towels provided
  • Shampoo
  • Hair dryer
  • Soap
  • Shower
Bedroom
  • Bed sheets provided
  • 2 bedrooms
  • Dining table
  • Living room
  • Wood stove
Kitchen
  • Coffee/tea maker
  • Oven
  • Refrigerator
  • Lobster/crab pot
  • Dishwasher
  • Spices
  • Blender
  • Microwave
  • Stovetop
Laundry
  • Washing machine and dryer
  • Laundry facilities
Ocean view
  • Near the beach
  • Beach towels
Parking
  • Onsite parking
  • Car recommended
Pet Friendly
  • Pet friendly
Accessibility
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Hardwood flooring in public areas
  • Area rugs in public areas
  • Tile flooring in public areas
  • Upper floors accessible by stairs only
  • 1 stairs to reach property
  • No elevators
  • Note from host: owner extremely allergic
  • Smoke-free property
  • Handrails in stairways
Activities
  • Bicycle on site
  • Winery tours nearby
  • Hiking nearby
  • Marina nearby
  • Jet skiing nearby
  • Power boating nearby
  • Golf nearby
  • Basketball nearby
  • Golf privileges
  • Sailing nearby
  • Cycling nearby
  • Kayak on site
Entertainment
  • Stereo
  • Games
  • Music library
  • Books
  • Smart TV with cable/satellite service
  • Video library
  • DVD player
General
  • Unit size: 1200 sq ft (111 sq m)
  • English
  • Italian
  • Near outlet shopping
  • Near a health or beauty spa
  • Near the bay
  • In the city center
  • Desk chair
  • Desk
Guest Services
  • Children's games
  • Children's toys
  • Stair gate
  • Iron/ironing board
  • Housekeeping (on request)
  • Safe
Internet
  • Free WiFi
Outdoors
  • Outdoor furniture
  • Patio
  • Charcoal grill
  • Garden
  • Firepit
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • First aid kit
  • Deadbolt lock
  • Fire extinguisher
Skiing
  • Close to skiing
Spa
  • Outdoor pool
  • Private pool

Policies

Check-in
Check-in time starts at 3:30 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:30 am contactless check-out available
Child Policy
Children are welcome. note from host: stairway up to second floor is steep-caution
Event Policy
No events allowed
Pet Policy
Note from host: $150 must declare or risk eviction-neighborwatch pets allowed service animals are welcome, and are exempt from fees
Smoking Policy
Smoking is not permitted;owner extremely allergic

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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Alyssa M.
Jun 29, 2025 09:57:13 PM
Review Score:   10
Summary: 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!!
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