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Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

Photo gallery for Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

Enjoy views of the Chesapeake Bay, pool and garden through a wall of glass!
The pool area is large and comfortable for the whole group! Pool is 16' x 32'
Poolside Activities... ready to handle this?
Dock, Firepit, Back Yard Hammocks or Kayaks. How many more ways to relax? Many!
Low tide beach. A shallow drop off means a wonderful play area for for kids!

Reviews

9.8 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 16

Popular amenities

  • Parking available
  • Kitchen
  • Fireplace
  • Washer
  • Dryer

Explore the area

Map
Wittman, MD
  • St. Michaels Marina
    ‪17 min drive‬
  • Chesapeake Bay Maritime Museum
    ‪17 min drive‬
  • St. Michaels Winery
    ‪18 min drive‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪41 min drive‬

Rooms & beds

5 bedrooms (sleeps 16)

Eagles Nest Suite

1 King Bed and 2 Double Futons

Falcons Perch

1 Double Bed

Fox Den Suite

2 Double Futons and 1 King Bed

Herons Hideaway Suite

1 King Bed and 2 Double Futons

Turtle Cove Suite

1 King Bed and 2 Double Futons

5 bathrooms

Eagles Nest Bathroom

Toilet · Shower only · Jetted bathtub

First Floor Bathroom

Bathtub or shower · Toilet · Shower only

Fox Den Bathroom

Toilet · Shower only · Jetted bathtub

Herons Hideaway Bathroom

Toilet · Shower only · Jetted bathtub

Outdoor Shower

Outdoor shower

Turtle Cove Bathroom

Bathtub · Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!

WATERMARK: A Relaxed, Spacious and Fun Chesapeake Bay Escape for Events, Extended Stays & Private Gatherings

Discover Watermark, a breathtaking 6,500 sq. ft. waterfront estate offering unparalleled views across 12 miles of the Chesapeake Bay. With spacious, light-filled interiors, four luxury master suites, a heated pool, and direct shoreline access, this extraordinary home is designed for relaxation, connection, and unforgettable memories.

We welcome guests to book for week-long to multi-week events retreats and private events such as:

✔ Family Gatherings & Multi-Generational Celebrations
✔ Weddings (On-Site Tent and Parking Space Available) & Rehearsal Dinners (Off-Site Ceremonies Welcome!)
✔ Corporate Retreats & Creative Workshops
✔ Wellness, Yoga & Inspiration Retreats
✔ Exclusive Photo & Film Shoots

We do not offer short-term vacation rental stays at this time and are only event based. Long-term rentals are a minimum of 13 weeks at special discount rates.

- Prime Location – Just 6 miles from the charming shops, restaurants, and attractions of St. Michaels and Tilghman Island.

Inside Watermark
Luxury Accommodations with Unforgettable Views
-Four Grand Master Suites – Each with a king-size bed, luxury linens, a private spa-style bathroom, and stunning water views. Suites also include a daybed and trundle, providing flexible sleeping arrangements.
- Wheelchair Accessible – First-floor access with no barriers.

Spacious Living Areas & Gourmet Kitchen
- Fully Equipped Chef’s Kitchen – Featuring a professional AGA stove and oversized island.
- Floor-to-Ceiling Bay Views – A wall of glass invites natural light and breathtaking scenery.
- Cozy Evenings – Enjoy the 75” & 84” 4K TVs, game room, bar area, and indoor fireplace.

Unplug, Recharge & Explore
- Heated Pool – Open April to October (weather-dependent).
- Private Beach & Dock – Swim, kayak, or crab at low tide (beach tide dependent)
- Outdoor Fire Pit & BBQ – Perfect for al fresco dining and evening gatherings.
- Incredible Wildlife Viewing – Spot bald eagles, herons, and osprey.

Exclusive Experiences at Watermark
- Scenic Bike Rides – Ride along the dedicated paths of Tilghman Island Road.
- Kayaking & Watersports – Five kayaks provided to explore the open bay.
- Crabbing at Low Tide – Simply wade in and see if you can net fresh Chesapeake blue crabs like the pros out there!

Plan Your Stay
- Available Year-Round – Enjoy seasonal specials with reduced rates through Memorial Day!
- Dog-Friendly – Up to 2 pets welcome ($100 per pet).
- High-Speed Internet – Perfect for remote work and extended getaways.

- Book Early – 2025 Availability is now Available!
- Experience the magic of Watermark – where relaxing meets nature on the Chesapeake Bay.

Note:
Watermark is not a short-term rental at this time. However, we welcome week to multi-week event stays and private events. We are an ideal home base for wedding guests, extended corporate groups, and special celebrations in the St. Michaels area.

Property manager

Nadir

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed: family gatherings, birthday parties, weddings
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Pets

Pets allowed: dogs less than 9 kg per pet (limit 2 pets total)
Well behaved dogs only w/additional fees , no cats
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Smoking

Smoking is not permitted
NO Smoking in & around the house!
Use of the pool & dock is strictly at your own risk.

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 75
Long-term renters welcome
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 first aid kit

We should mention

A car is recommended for transport to and from this property

About the area

Wittman

Located in Wittman, this holiday home is on the waterfront. The area's natural beauty can be seen at Wittman Park and CL Open Field, while Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum are cultural highlights. Discover the area's water adventures with waterskiing and water tubing nearby, or enjoy the great outdoors with hiking and ecotours.
Map
Wittman, MD

What's nearby

  • St. Michaels Marina - 17 min drive - 16.1 km
  • Chesapeake Bay Maritime Museum - 17 min drive - 16.1 km
  • St. Michaels Museum - 17 min drive - 16.5 km
  • St. Michaels Winery - 18 min drive - 16.8 km
  • Saint Michaels Village - 20 min drive - 18.2 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 32 min drive

Restaurants

  • ‪Foxy's - ‬12 min drive
  • ‪Chesapeake Landing Restaurant - ‬7 min drive
  • ‪The Blue Crab - ‬11 min drive
  • ‪Carpenter Street Saloon - ‬11 min drive
  • ‪The Crab Claw - ‬12 min drive

Frequently asked questions

Does Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings! have a pool?

Yes, this property has an outdoor pool. Pool types include heated pools.

Is Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings! pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 9 kg per pet.

What time is check-in at Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!?

Check-in begins at 4:00 PM.

What time is check-out at Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings!?

Checkout is at 10:00 AM.

Where is Comfortable Spacious Fun! 6+Acres Pool+Bay Waterfront St Michaels-Yes Weddings! located?

This family-friendly Wittman holiday home is located on the waterfront, 0.9 mi (1.5 km) from Wittman Park, and within 6 mi (10 km) of CL Open Field and Goat Island. Back Creek Community Park and Knapp's Narrows Marina & Inn are also within 6 miles (10 km).

Reviews

9.8

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. 70 out of 77 reviews
Rating 8 - Good. 6 out of 77 reviews
Rating 6 - Okay. 0 out of 77 reviews
Rating 4 - Poor. 0 out of 77 reviews
Rating 2 - Terrible. 1 out of 77 reviews

9.8/10

Cleanliness

9.8/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Martha H.

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

Escape from it all

As soon as you step into Watermark, you begin your escape. The house is designed to provide cozy gathering spaces and the yard though large is framed by trees making it an enclosed space. We enjoyed feeding the turtles in the pond which is right on your doorstep. The dock provides a pleasant place to enjoy nature and beautiful sunsets.
Stayed 7 nights in Aug 2024

10/10 Excellent

Karen G.

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

A wonderful family vacation

We truly loved Watermark with its spaciousness and lovely property. As someone who loves to cook I found the kitchen well equipped and we enjoyed family meals together. Beds were very comfortable and sunsets were unbelievably beautiful. I highly recommend Watermark and Nadir was a pleasure to work with
Stayed 14 nights in Jun 2024

10/10 Excellent

samantha e.

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

Fun

It was wonderful
Stayed 5 nights in Aug 2023

8/10 Good

Daniel M., Lancaster, PA USA

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

Whittman Summer Holiday

It was a family vacation with our 3 Grandchildren, ages 4, 9, and 12. The best aspect was the easy access to the Bay and kayaking for our older Grandchildren. The children could wade quite far and only be up to their thighs. The house was large and spacious providing many place for the children to play. Every night, we enjoyed the fire pit. The house is older, but it worked well for us as a large family group.
Stayed 8 nights in Aug 2023

10/10 Excellent

Betsy G., WINCHESTER

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

Great family vacation

This home has a terrific setting - beautiful sunsets, kayaks to borrow, fabulous hammocks, and so much room! All the bedrooms are large and let folks spread out and come together . We loved the kitchen because most meals were at home as we centered around a three month old! We loved doing a puzzle together and the fun games on the game porch. Nadir is on top of everything and very helpful. Highest praise of all? One of my kids wants to rebook the home with his friends as soon as he can! Thanks Nadir.
Stayed 7 nights in Jun 2023

10/10 Excellent

Katie K.

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

Peaceful stay, perfect for families

We loved Nadir’s home. It is huge and homey, and the setting is so peaceful. The sunsets are out of this world. The beds are cozy, unlike many rental beds we’ve experienced. There was plenty of room for everyone. Nadir was a wonderful host-very communicative the entire time. The location is perfect. Very close to St. Michael’s, which has tons of cute shops and restaurants. Our kids loved the heated pool. We definitely recommend and if we come back to St. Michael’s we would definitely look to rent again.
Stayed 7 nights in Jun 2023

10/10 Excellent

Bev S., North Carolina

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

Wonderful

This is a beautiful and very comfortable property that has absolutely everything you need. Plenty of room to spread out and perfect common areas to gather for fun and games. The pool was a delight as was the pier and beautiful views. Comfortable beds and furniture. Host was wonderful, great place for a vacation for young and old alike!
Stayed 3 nights in May 2023

10/10 Excellent

Chris M.

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

Girlfriend get away

We had a wonderful time at this beautiful property. The owner was very responsive and responded to any issues right away.
Stayed 3 nights in May 2023

10/10 Excellent

Chris F., McLean

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

Comfortable

This home is so cozy to stay in, lovely views of the water, great fire pit and really private.
Stayed 5 nights in Nov 2022

10/10 Excellent

Pon K.

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

A home with all you need

Home was clean, had all the amenities for a 8 family and friends to enjoy. Very spaces, larger than it looks in the pictures. We crabbed and caught 11, kayaked, grilled seafood from Whittman’s Warf (where their tuna and salmon were sushi-grade and oysters were sucked), cooked, swam in the pool, played games, used both TVs for the US Open and exercising. The two dish washers and two fridges and the ice maker were nice as the main dish washer stopped working on our last night there. Since it was cloudy we were only able to get in two nice sunsets. Nadir was responsive and accommodating, even when I forgot something and had to go back to the house after checkout. One thing that can be better is while the stove and oven are sophisticated and large, you have to hold the gas switch for 20 secs before the light comes on, which was not convenient for my Mom or other cooks in the house. House tour was good and we had a great time at the house.
Stayed 7 nights in Sep 2022

10/10 Excellent

Jason K.

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

Great place

Great place, had a nice time. Kitchen is beautiful. The pool is shaded part of the day which was perfect for us. A very short drive into St Michael's. We wish the house had been closer to the water.
Stayed 7 nights in Jul 2022

10/10 Excellent

Sally Y.

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

Family Vacation

The location is great. It's easy to get to St. Michaels for shopping and some meals. The beach, when the tide is out, is loads of fun for youngsters. The view of the bay was beautiful, spectacular from the second floor. Our grandsons referred to the game room as THEIR toy room. The heated pool was wonderful, and the house was big enough that everyone had their own space.
Stayed 7 nights in Jul 2022

10/10 Excellent

Charles B.

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

Beautiful Property just outside of Saint Michaels

Property and House is exactly as depicted. Enormous rooms throughout home, living space and bedrooms. The kitchen is great and really is supplied with everything you need, even spices and oils, we brought a lot of things with us that we did not even need to unpack. we had five couples, all family plus a six month old, we had more than enough room and never felt cramped. The pool was great, and everyone loved feeding the turtles in the pond. Easy access to the bay right on the property, five kayaks available to use. Actually too many good points to mention them all. Highly recommend!
Stayed 7 nights in Jul 2022

10/10 Excellent

Barbara P.

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

Extended Family Week

Our host, Nadir, was helpful and very responsive to any needs or questions that arrived. My 5 young grandchildren loved the pool and spent hours in it each day. We kayaked, fed the turtles, played on the piano and with the many games available. The back yard is beautiful and so relaxing. It was a wonderful vacation and we had a terrific time.
Stayed 7 nights in Jun 2022

10/10 Excellent

Vera H., Ellicott City, Md

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

Relaxing and rejuvenating

This was our second stay at this property. The owner is kind and receptive and will answer any concern or question without hesitation. I feel very comfortable as as guest. My family looked forward to coming back this time and has asked to stay again. Thank you for giving us a short respite from the daily grind.
Stayed 3 nights in Jun 2022

10/10 Excellent

jamaal s.

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

The place you tell stories about

My family and I have been renting homes in the Saint Michael's area for years and each trip we have some wish list that isn't completely filled. This was the first year that every wish was met. For setting to privacy to pool to amenities to etc..... So if you're looking for "that place" this is it.
Stayed 5 nights in Jun 2022

10/10 Excellent

Alfred G.

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

Watermark stay

A perfect setting and accommodations for our college and Army friends of over 50 years. Relaxing space for casual conversation and a convenient location as we explored the St Michaels area.
Stayed 3 nights in May 2022

10/10 Excellent

Wendy T.

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

Excellent

Had a yoga retreat with friends and everything was amazing. Gorgeous house, grounds, water access, location! Kitchen was very well stocked and pool was lovely and heated even during a cold drizzly weekend. Definitely recommend it and will return!
Stayed 3 nights in May 2022

10/10 Excellent

Nicole B.

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

Amazing house!

This house was perfect for a girls weekend. The house was huge and there is plenty is space to spread out. The pool and outside area is perfect. It is a short drive into town. 10/10, we can’t wait to rent it again!
Stayed 4 nights in Sep 2021

10/10 Excellent

Rahul K.

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

Wonderful family getaway in Chesapeake

Watermark is a fantastic property for a large family get-together - spacious, clean, well-maintained and well-equipped.. Plus Nadir was an amazing host throughout. The sunsets were breathtaking, and we got to witness hundreds of migratory birds flying across the Bay. We would love to be back!
Stayed 4 nights in Dec 2021

10/10 Excellent

emily d., Washington, DC

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

Santa made it to Wittman

Enjoyable family vacation to the St. Michaels area! The home pleasantly accommodated our crew, and we made full use of the kitchen and main fireplace every night. The sunsets are breathtaking from the dock, and Nadir is a very welcoming host. Thank you again!
Stayed 3 nights in Dec 2021

10/10 Excellent

ALISON H.

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

reunion gathering

nadir is the perfect host...there to greet and explain, easy to reach during stay. house is incredibly comfortable with privacy and comfort. the grounds are gracious. we would go back in a heartbeat
Stayed 5 nights in Oct 2021

10/10 Excellent

Emily R.

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

Family Vacation

We had a wonderful time at Watermark! The house and property were perfect for our group. There were three families with kids, and the spacious house allowed for everyone to have privacy during the stay. The main living area is very comfortable, and was perfect for kids. The game room was an added bonus, lots of fun for both kids and adults. The house was very private, and in a great location. Thanks for a great stay!
Stayed 3 nights in Oct 2021

10/10 Excellent

Michelle Z.

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

Wonderful long weekend

We all enjoyed an absolutely wonderful long weekend in Wittman! It was a wonderful house, beautiful property, so relaxing- and such a great place for people of all ages. We want to thank Nadir for being a wonderful host and we can’t wait to come back and enjoy this property again.
Stayed 3 nights in Oct 2021

10/10 Excellent

Marcy F.

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

Great Retreat

Watermark is a wonderful place to host family and friends. We rarely left the property as it was so comfortable and accommodating. Nadir is a great host and was readily accessable to respond to any questions. Will be back!
Stayed 11 nights in Sep 2021

About the host

Hosted by Nadir

Host profile image
Professional property manager with decades of experience pampering guests.

Why they chose this property

It's simply amazing. Great energy flow. Surrounded by wetlands and woods. Large open spaces inside that just allow everyone to relax and enjoy. Love the log cabin feel.

Languages:

English