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

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

Reviews

9.4 out of 10, Loved by Guests
Top 10% based on
4 bedrooms3+ bathroomsSleeps 8223.0 sq m

Popular amenities

  • Ocean view
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer

Explore the area

View map
St Michaels, MD
  • Place, St. Michaels Winery
    ‪8 min drive‬
  • Place, St. Michaels Marina
    ‪8 min drive‬
  • Place, Chesapeake Bay Maritime Museum
    ‪8 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪26 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.

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

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. St Michaels Nature Trail and Clint S. Bradley Park reflect the area's natural beauty and area attractions include Chesapeake Bay Maritime Museum and Easton Cycle and Sport.
View more Holiday homes in St. MichaelsOpens in a new window
Map
St Michaels, MD

What's nearby

  • St Michaels Nature Trail - 6 min drive - 3.4 km
  • Perry Cabin Park - 7 min drive - 4.1 km
  • St. Michaels Winery - 8 min drive - 3.9 km
  • St. Michaels Marina - 8 min drive - 3.9 km
  • Chesapeake Bay Maritime Museum - 8 min drive - 4.5 km

Getting around

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

Restaurants

  • ‪Stars - ‬10 min drive
  • ‪The Crab Claw - ‬9 min drive
  • ‪Carpenter Street Saloon - ‬9 min drive
  • ‪Foxy's Harbor Grille - ‬10 min drive
  • ‪t at The General Store - ‬16 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.

How much does it cost to stay at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels?

As of 21 March 2026, prices found for a 1-night stay for 2 adults at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels on 30 May 2026 start from NZ$1,448, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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.

How much is parking at Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels?

On-site parking is available at the property.

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).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 47 out of 59 reviews
Rating 8 - Good. 6 out of 59 reviews
Rating 6 - Okay. 6 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 reviews

9.4/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Randi W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect. Views of the water, the pool and easy drive into town made for a relaxing getaway!
Stayed 6 nights in Aug 2025
Verified

8/10 Good

Melissa D.

Liked: Check-in, communication, location, listing accuracy

Great Dock for Morning Coffee

Fantastic location on the water. Great communication. Renovation is nice with good spaces for families.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Rita M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely retreat!

Great relaxing stay!
Stayed 3 nights in Dec 2020
Verified

10/10 Excellent

Laurel G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful and Convenient

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.
Stayed 3 nights in Jun 2025
Verified

10/10 Excellent

Patricia O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Back of the house, looking from the dock
Beautiful Pool view
Early morning mist from the back yard looking at the dock and river
Pathway to the dock
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Maria M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

50th Birthday celebration

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!
Stayed 3 nights in Apr 2025
Verified

10/10 Excellent

Crystal T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location, lots to do!

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.
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Dominick F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation

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.
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Lisa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing getaway

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.
Stayed 3 nights in Jun 2024
Verified

10/10 Excellent

Danielle S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Setting

The decor was a little dated but all in all the house was spacious and clean and the updated kitchen was well-stocked. The pool and setting were gorgeous!
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

momod54 m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip for birthday

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
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

david r h.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Crabbing

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.
Stayed 5 nights in Aug 2024
Verified

10/10 Excellent

karen b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

St. Michaels

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.
Stayed 7 nights in Jun 2024
Verified

8/10 Good

John W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice house on the water

Enjoyed our stay. House is about 7 minutes drive from downtown at st. Michael's. Nice pool and dock. Screened porch was a bit damp and dank, but could be due to day of rain at the time of our arrival.
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

Anne L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend getaway

Lovely and relaxing waterfront location. An easy drive into town but warmer weather stays would be an easy bike ride into town. Lots of space to hang out and it is definitely a great place for summer time fun. The only draw back is that you have to walk through one of the bedrooms to get into the master bedroom but if you’re staying with family, this is not a big deal. We would definitely stay here again!
Stayed 2 nights in Nov 2021
Verified

10/10 Excellent

Swathi B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect St. Michael's Vacation

We stayed to celebrate my parents' 40th wedding anniversary. Our group was 6 adults and 2 toddlers and the house was perfection. Beautiful backyard, spacious house, close proximity to St. Michael's so we could pop over for lunch or ice cream. We biked into town, kayaked, enjoyed the pool, and loved every minute. Note that the pool is in the shade for much of the day, which for us was good for avoiding the heat and constant sunscreen reapplication for the kids, but does mean that it's a little cold. Ignore any of the less-than-stellar reviews. Everything was clean, in good condition, and appropriate for a vacation home in the area.
Stayed 5 nights in Jun 2021
Verified

6/10 Okay

Garland A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pretty spot, house disappointing

For the money, we were a bit disappointed with the house. It is much smaller than was expected, queen beds only and no amenities such as shampoo, soap, etc... The front yard looked quite nice, but we were in town for a wedding and did not have time to enjoy the outside.
Stayed 2 nights in Oct 2020
Verified

10/10 Excellent

Jenna F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for Family First Retreat

Bay Cottage was the perfect home for our extended family vacation. The home is situated on a lovely corner of waterfront. Kayaks and bikes are great options for exploring land and sea! The kitchen is very well equipped for any of your needs including crab mallets! The communication with the host was quick and very helpful! Pool is fantastic! Shaded in the morning and sunkissed mid-afternoon! There are many games and books for down time. Getting to and from town is a piece of cake! Everyone from age 3 to 43 was happy throughout the stay! We will be coming back for years to come!
Stayed 4 nights in Aug 2021
Archival

10/10 Excellent

Excellent for a Family Week-end

My family & I spent a wonderful, amazing week-end at this house. We were 5 adults and 3 children. Everyone was in love with the property. The pool was totally private and the view to the bay was beautiful. The private dock was so peaceful, too. We also loved hanging out on the screened-in porch. The listing description was totally accurate, as were the photos. Everything was clean and well-maintained. and the owner was very helpful in answering our questions. Although St. Michaels seemed to be a charming town, we never got there to browse. We only drove in for dinner because we just didn't want to leave the property. I would definitely recommend this property to friends and relatives.
Verified

6/10 Okay

Patty M.

Liked: Cleanliness, check-in, communication, listing accuracy

Girls weekend celebration

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
Stayed 4 nights in Jun 2021
Verified

8/10 Good

Noshin Q.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation spot

This is a great property to vacation with your family. Best part is the pool that kids enjoyed most. just 3 miles from downtown.
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Lindsay S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful yard!

We loved the yard and they views were beautiful. The kayaks were fun as well. Very cute and quaint!
Stayed 5 nights in Sep 2021
Verified

10/10 Excellent

Teresa M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect family getaway, BEAUTIFUL views and water access

We spent the weekend away with our children and in-laws. We have always loved the town of St. Michaels, but having a full house and direct water access made this trip all the more special. The property is just as described-- private dock access, big yard, pool, kayaks, and bikes. Rita is an excellent host and very responsive. The yard is beautiful, quiet and peaceful. Thank you!
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Simone W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Vacation

The Bay Cottage was just what our family needed after not getting to travel last summer. Location is close to restaurants and shopping in St. Michaels but far enough away to be private. Views, pool, and spa were great. Kayaks were an added bonus. Rita was very responsive to all our questions and the house was clean and comfortable.
Stayed 6 nights in Jun 2021
Verified

10/10 Excellent

Sharon O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views

Our family really enjoyed our stay…swimming, kayaking. Great house
Stayed 5 nights in Jun 2021

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

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