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Saint Michaels, Maryland

St. Michaels Escape | Pool, Hot Tub & Fire Pit

3 bedrooms3 beds2.5 baths6 guests

Peaceful waterfront retreat minutes from St. Michaels. Relax by the pool and in the hot tub, enjoy coffee on the dock, or gather around the fire pit. The Kipsy offers space, comfort, and stunning views for families and friends.

Talbot County Licensure: STRN-26-44

Welcome to The Kipsy, a one-level waterfront escape on a peaceful peninsula. Inside, you’ll find an open-concept living area, a chef’s kitchen, and large windows framing water and pool views. The primary suite overlooks the creek and features a spa-like bath. Two guest bedrooms (king, queen + twins) ensure everyone sleeps in comfort.

Step outside to your private paradise: a pool, hot tub, dock, hammock, and fire pit—perfect for sun-soaked afternoons and cozy evenings. Whether you’re entertaining, adventuring, or relaxing, The Kipsy has it all.

What you'll love:
✔️ Private pool & hot tub
✔️ Dock access for boating, fishing & crabbing
✔️ Fire pit with seating for evening gatherings
✔️ Keyless entry for easy check-in

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.

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 April 15, 2026.

Property License: STRN-26-44

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (excl. fees and taxes)AvailabilityMin Stay (nights)
Nov 13, 2026$845Not Available3
Nov 14, 2026$845Not Available3
Nov 15, 2026$845Available3
Nov 16, 2026$845Available3
Nov 17, 2026$845Available3
Nov 18, 2026$845Available3
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Nov 20, 2026$845Available3
Nov 21, 2026$845Available3
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Nov 25, 2026$845Available3
Nov 26, 2026$845Available3
Nov 27, 2026$845Available3
Nov 28, 2026$845Available3
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Nov 30, 2026$845Available3
Dec 1, 2026$845Available3
Dec 2, 2026$845Available3
Dec 3, 2026$845Available3
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Dec 5, 2026$845Available3
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What this home offers

Pool outdoor
Hot tub
BBQ Area
Air conditioning
Bathtub

Where you’ll be

Saint Michaels, Maryland, 21663, United States

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Check-in & check-out

Check-in after 5:00 PM.

Check-out before 10:00 AM.

Property rules

Children welcome (2–12 years).

Infants welcome (under 2).

Maximum 6 guests.

No pets allowed.

No parties or events.

Cancellation policy

Add your trip dates to get the cancellation details for this stay.