Entire home
St. Michaels Escape | Pool, Hot Tub & Fire Pit
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Reviews
10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 6
Popular amenities
Explore the area

Saint Michaels, MD
- Place, Perry Cabin Park4 min drive
- Place, St. Michaels Marina6 min drive
- Place, Chesapeake Bay Maritime Museum6 min drive
- Airport, Easton, MD (ESN-Easton - Newnam)25 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1
1 Queen Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Beds
2 bathrooms, 1 half bathroom
Bathroom
Bathtub · Toilet · Shower only
Bathroom #2
Toilet · Shower only
Bathroom #3
Toilet
Spaces
Kitchen
Office
Balcony
Garden
Dining area
About this property
St. Michaels Escape | Pool, Hot Tub & Fire Pit
Summary:
Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. With a pool, hot tub, fire pit, and private dock, this home is the perfect balance of relaxation and adventure for families and groups.
Talbot County Licensure: STRN-24-49
The Space:
Inside, The Kipsy features an open, light-filled layout with modern furnishings and panoramic creek views. The gourmet kitchen is fully equipped for entertaining, while the large dining area and cozy living room invite family meals and movie nights. Three comfortable bedrooms provide restful retreats. With multiple indoor and outdoor spaces, the home easily accommodates families, friends, or groups celebrating special occasions.
The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for weddings, family reunions, or a peaceful Eastern Shore getaway.
What you'll love:
- Sparkling private pool with sun loungers
- Hot tub overlooking the creek for year-round relaxation
- Evening gatherings around the fire pit under the stars
- Private dock ideal for fishing, crabbing, or launching kayaks
- Spacious, open-concept living areas with water views
- Just minutes to St. Michaels restaurants, shops, and harbor
Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.
Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.
The Neighborhood:
The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for family reunions, or a peaceful Eastern Shore getaway.
Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.
The private pool is scheduled to open for the season on March 15, 2026.
Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. With a pool, hot tub, fire pit, and private dock, this home is the perfect balance of relaxation and adventure for families and groups.
Talbot County Licensure: STRN-24-49
The Space:
Inside, The Kipsy features an open, light-filled layout with modern furnishings and panoramic creek views. The gourmet kitchen is fully equipped for entertaining, while the large dining area and cozy living room invite family meals and movie nights. Three comfortable bedrooms provide restful retreats. With multiple indoor and outdoor spaces, the home easily accommodates families, friends, or groups celebrating special occasions.
The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for weddings, family reunions, or a peaceful Eastern Shore getaway.
What you'll love:
- Sparkling private pool with sun loungers
- Hot tub overlooking the creek for year-round relaxation
- Evening gatherings around the fire pit under the stars
- Private dock ideal for fishing, crabbing, or launching kayaks
- Spacious, open-concept living areas with water views
- Just minutes to St. Michaels restaurants, shops, and harbor
Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.
Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.
The Neighborhood:
The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for family reunions, or a peaceful Eastern Shore getaway.
Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.
The private pool is scheduled to open for the season on March 15, 2026.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning
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10.0 out of 10, Exceptional, (68 reviews)
House Rules
Check in after 5:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed, service animals permitted
Smoking
Smoking is not permitted
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
St. Michaels
Located in St. Michaels, this holiday home is on the waterfront. Chesapeake Bay Maritime Museum and Phillips Wharf Environmental Center are local attractions and those in the mood for shopping can visit Saint Michaels Village and Queenstown Premium Outlets. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

Saint Michaels, MD
What's nearby
- Perry Cabin Park - 4 min drive - 3.8 km
- St. Michaels Marina - 6 min drive - 4.8 km
- Chesapeake Bay Maritime Museum - 6 min drive - 4.8 km
- 1879 Hooper Straight Lighthouse - 6 min drive - 4.8 km
- St. Michaels Winery - 6 min drive - 5.5 km
Getting around
Restaurants
- Stars - 6 min drive
- The Crab Claw - 6 min drive
- Carpenter Street Saloon - 6 min drive
- Foxy's Harbor Grille - 7 min drive
- t at The General Store - 13 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
9.6/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
29 Mar, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Mar 2025
10/10 Excellent
Tracey W.
18 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




Tracey W.
Stayed 3 nights in Sep 2025
10/10 Excellent
Kristen K.
8 Aug, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful Vacation

Kristen K.
Stayed 4 nights in Aug 2025
10/10 Excellent
Larry I.
23 Oct, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Short retreat
Larry I.
Stayed 3 nights in Sep 2024
10/10 Excellent
Jill C.
4 Aug, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
ST. Michaels annual family vacation
Jill C.
Stayed 7 nights in Jul 2024
About the host
Hosted by Jennifer Brown
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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