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

Saint Michaels, Maryland
$1056 avg/night
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 20 Lbs Per Pet) Pet Friendly Welcoming Cats And Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2400 Sq Ft (223 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Outdoor Furniture Patio
  • POOL/SPA

    Hot Tub Outdoor Pool Private Pool
  • BATHROOMS

    3.5 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Bicycle On Site Kayak On Site
  • ENTERTAINMENT

    DVD Player Music Library Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    Near The Ocean Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 03:30 PM CheckOut Check-out : 10:30 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Rates & Availability

Review Review

  • Randi W.

    Submitted Sep 22, 2025

    Stayed Aug 28, 2025

    The house was perfect. Views of the water, the pool and easy drive into town made for a relaxing getaway!

  • Melissa D.

    Submitted Aug 4, 2025

    Stayed Jul 31, 2025

    Fantastic location on the water. Great communication. Renovation is nice with good spaces for families.

  • Patricia O.

    Submitted Jul 14, 2025

    Stayed Jun 22, 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.

  • Laurel G.

    Submitted Jun 23, 2025

    Stayed Jun 19, 2025

    Great stay - the house is so much larger than it seems. We loved the waterfront location, nice yard, and pool. Great location for access to St. Michael's and surrounding area. Had a wonderful time catching up with family at Two Oysters. Would stay again.

  • Maria M.

    Submitted May 1, 2025

    Stayed Apr 24, 2025

    The place was awesome. It was so cute and quaint. It was well decorated and plenty of room. The beds were super comfortable! Loved the outdoor deck and screened in porch. They had bikes we could use too! Highly recommend!

  • david r h.

    Submitted Sep 9, 2024

    Stayed Aug 29, 2024

    We enjoyed crabbing off the dock, kayaking to town for breakfast, using the pool and hottub as well as hearing nature outside. The house was spacious enough to meet our needs.

  • momod54 m.

    Submitted Aug 11, 2024

    Stayed Aug 4, 2024

    My family and I enjoyed our trip to Saint Michaels. There was so much for the kids to do-pool kayak fishing Bike riding. They stayed busy morning tonight while the adults relaxed. Such a beautiful, peaceful location. We can’t wait to go back

  • Dominick F.

    Submitted Jul 26, 2024

    Stayed Jul 10, 2024

    We had an awesome vacation. Very relaxing very quiet. House was clean well put together a lot of activities. Close to town yet far enough away for privacy. Will go there again.

  • Crystal T.

    Submitted Jul 20, 2024

    Stayed Jul 15, 2024

    The many amenities kept everyone busy, from crabbing, kayaking, swimming, running or biking into town. The property is shaded from the heat and had a very peaceful woodland feel.

  • karen b.

    Submitted Jul 7, 2024

    Stayed Jun 30, 2024

    We loved our vacation in St. Michaels! The house is beautiful and wonderfully well equipped. The owners were lovely and responded so quickly to all of our inquiries! The pool & view of the water are truly incredible! Just a truly special time with our family.

  • Lisa C.

    Submitted Jun 22, 2024

    Stayed Jun 17, 2024

    We had a wonderful stay in this beautiful home. Plenty of room to relax and unwind. The walk out dock was so nice, and we enjoyed using the kayaks. The pool was refreshing and perfect for for a girls' vacay. Owner was very responsive too.

Your dates are Available!

Total

Includes taxes and fees
$1,056+
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