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Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Waterfront holiday home with outdoor pool and Hot tub

Photo gallery for Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

Waterfront house with private pool and dock
Interior
Dining
private salt water pool overlooking bay. Large pool
dining room with water views

Reviews

9.4 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 82400 sq ft

Popular amenities

  • Parking available
  • Hot tub
  • Pet-friendly
  • Kitchen
  • Barbecue grill

Explore the area

View in a map
St Michaels, MD
  • Place, St. Michaels Winery
    ‪9 min drive‬
  • Place, St. Michaels Marina
    ‪9 min drive‬
  • Place, Chesapeake Bay Maritime Museum
    ‪9 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪32 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

3 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet · Shower only

Bathroom#3

Toilet · Shower only

Outdoor Shower

Outdoor shower

Spaces

Deck or patio
Outdoor shower
Kitchen
Outdoor play area
Dining area

About this property

Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels

The Two Oysters House finished renovations in 2025, featuring spectacular views from almost every room, a large private pool 18x 26ft (salt water), and a dock. The location is a couple of miles from the center of St. Michaels (Museum and Inn at Perry Cabin)- close enough to bike into town and just far enough for privacy. Bikes, kayaks, fresh linen, and bath towels are included in the rental rate.

***Weekly rentals are preferred in the summer. (July and August)
3nt.min stay sleeps 8. Talbot County license ST-797-HOP 2019

Thinking vacation should be watching sailboats from the pool, kayaking to a nearby island with a sand beach, biking into town for ice cream, or napping on the hammock. Boating options and sunset cruises are available in the town of St. Michaels May-Oct.

The Two Oysters house is a short bike ride to the museum/lighthouse, restaurant, quaint shops, ice-cream parlors, cafes, bistros, brewery, and winery. You're welcome to use bikes and kayaks at the house (4-6 adult bikes 2-3 kid bikes, 4 adult kayaks and 2 kid water kayak) or feel free to bring yours.

The house is on 6 acres of wooded retreat located right on the Chesapeake Bay (San Domingo Creek) with a new private pool (18x36 ft) with a spa. Spa heating options may be available with an additional utility fee. Please ask before booking. The pool/spa opens in May and closes in September.

The house layout makes you feel like you are outdoors in almost every room overlooking the water and beautiful tall pine trees. View of amazing sunrise from house and dock every morning. 2 master bedrooms with private baths. 4 bedroom total (3 full bathrooms). Separate additional den/tv room.

Whether lounging by the pool overlooking the bay, crabbing on the dock, kayaking, biking, or exploring the 6 acres of woods, there is something for everyone of all ages.

No parties, weddings, rehearsal dinners, receptions, banquets, corporate retreats, or similar activities are allowed at the house.

Keywords: St. Michaels, waterfront, house, cottage, bay, pool, spa, dock, hot tub, bike, kayak, boat, fish, crab, in-ground pool,
For security purposes, the owners will never ask you to make any payments via wire transfer. Beware of any response seeking payment via wire transfer.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly

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House Rules

Check in after 3:30 PM
Minimum age to rent: 23
Check out before 10:30 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs and cats less than 9 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted
No weddings or parties.
No smoking.
No Fire pits

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 and a deadlock
Property Registration Number STN-24-42

About the area

St. Michaels

Located in St. Michaels, this holiday home is on the waterfront. Chesapeake Bay Maritime Museum and St. Michaels Museum are cultural highlights, and some of the area's attractions include Easton Cycle and Sport and Phillips Wharf Environmental Center.
Map
St Michaels, MD

What's nearby

  • St. Michaels Winery - 9 min drive - 3.9 km
  • St. Michaels Marina - 9 min drive - 3.9 km
  • Chesapeake Bay Maritime Museum - 9 min drive - 4.5 km
  • 1879 Hooper Straight Lighthouse - 9 min drive - 4.5 km
  • Saint Michaels Village - 10 min drive - 5.2 km

Getting around

  • Cambridge Station - 49 min drive
  • Easton, MD (ESN-Easton - Newnam) - 29 min drive

Restaurants

  • ‪Stars - ‬10 min drive
  • ‪Foxy's Harbor Grille - ‬10 min drive
  • ‪Carpenter Street Saloon - ‬9 min drive
  • ‪Purser's Pub - ‬10 min drive
  • ‪The Crab Claw - ‬9 min drive

Frequently asked questions

Does Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels have a pool?

Yes, this property has an outdoor pool.

Is Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels pet-friendly?

Yes, this property allows cats and dogs (limit 1 total) with a maximum weight of up to 9 kg per pet.

What time is check-in at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels?

Check-in begins at 3:30 PM.

What time is check-out at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels?

Checkout is at 10:30 AM.

Where is Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels located?

Situated on the waterfront, this holiday home is within 3 miles (5 km) of St Michaels Nature Trail, Clint S. Bradley Park and Higgins Yacht Yard and Marina. Chesapeake Bay Maritime Museum and Muskrat Park are also within 3 miles (5 km).

About the host

Hosted by Rita

Host profile image
A nearby escape from the DC area- to detox from electronics and be more with face time with family... is always good

Why they chose this property

A waterfront home inside the town of St. Michaels is the most ideal. A perfect and close escape for a romantic get-a-way, relaxing retreat or entertaining family and friends. Shorter trip. Longer vacation.
Less than a couple of hours from home and just a short bikeride into town for ice-cream. Perfect.

What makes this property unique

Being right on the water from sunrise to sunset..... savoring the good life. Swimming just a few steps from house makes the best vacation

Languages:

English

Premier Host

They consistently provide great experiences for their guests