Entire home
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Waterfront holiday home with outdoor pool and Hot tub
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Reviews
9.4 out of 10
Exceptional
4 bedrooms 3+ bathrooms Sleeps 8 2400 sq ft
Popular amenities
Explore the area

St Michaels, MD
- Place, St. Michaels Winery9 min drive
- Place, St. Michaels Marina9 min drive
- Place, Chesapeake Bay Maritime Museum9 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.
***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
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs and cats less than 9 kg per pet (limit one pet total)
Smoking
Smoking is not permitted
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.

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
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
About the host
Hosted by Rita

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.
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
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