House in Maryland
8 guests · 4 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
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.
Amenities at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
Non-smoking
Pets allowed
Family friendly
Map of Maryland
Ratings and reviews
10 / 10Outstanding·Sep 2025
The house was perfect. Views of the water, the pool and easy drive into town made for a relaxing getaway!
8 / 10Excellent·Aug 2025
Fantastic location on the water. Great communication. Renovation is nice with good spaces for families.
10 / 10Outstanding·Jul 2025
The house and property were lovely. There was enough room for everyone. We enjoyed the pool and screened in porch as MD weather decided to be in the 90's. The location is great. It's so close to town yet rural enough to be very quiet.
6 / 10Average·Jun 2021
Views from the house were lovely and descriptions are pretty accurate. Our only disappointment was that the house is getting a little rundown. The kitchen table has peeling paint, the outside furniture cushions are stained, curtains throughout the whole house are old and looking shabby with no true window blinds good enough curtains to block out the sun in the bedrooms especially the two that face the back of the house for when the sun rises at 5:30 in the summer mornings. Not enough furniture in the bedrooms to have places to put your suitcases. Mattresses seem old and uncomfortable with homemade headboards that do not attach to the bed so when you roll over they bang against the wall. Front of house needs weeding and trimming. So overall we had a decent stay but for the money we would not return for a second rental
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Top rated by guests
9.4Outstanding
(59 Ratings)
"The house was perfect. Views of the water, the pool and easy drive into town made for a relaxing getaway!"
Randi W.Don't miss out! Price and availability may change
