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

Waterfront holiday home with private pool and kitchen

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!
Crabs netted at low tide by kids and adults being kids, right off Watermark.
Watermark nights are amazing! Relish the dark starry sky and amazing Milky Way
Walk in to a wall of glass overlooking the Chesapeake. Savor space to breath!
Relax in 30x30 vaulted ceiling Living Room. Cozy wood stove! Music+Games+TV 75"

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Parking available
  • Laundry
  • Kitchen
  • Pet-friendly
  • Air conditioning
AU$1,648
avg per night

Explore the area

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Wittman, MD

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
The current price is AU$1,648
avg per night

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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 cycling.
View more Lodges in WittmanOpens in a new window

Getting around

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

Restaurants

  • ‪Stars - ‬11 min drive
  • ‪Foxy's Harbor Grille - ‬13 min drive
  • ‪Carpenter Street Saloon - ‬12 min drive
  • ‪The Crab Claw - ‬12 min drive
  • ‪Chesapeake Landing - ‬7 min drive

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

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

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 events and private events.

Amenities

Pool
Pet-friendly
Free WiFi
Air conditioning
Parking available
Laundry

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
default

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

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

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

9.8

Exceptional

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.6/10

Location

9.6/10

Listing accuracy
Rating 10 - Excellent. 70 out of 78 reviews
Rating 8 - Good. 6 out of 78 reviews
Rating 6 - Okay. 0 out of 78 reviews
Rating 4 - Poor. 1 out of 78 reviews
Rating 2 - Terrible. 1 out of 78 reviews

Reviews

This review was submitted before 2018 and has not been verified.

10/10 Excellent

James B.

Excellent place for families

Our third year spent here with our family. We appreciated the excellent service by Ms Focht.
Stayed 7 nights in Jun 2017

10/10 Excellent

Keith M.

Beautiful property

Beautiful, well-maintained property directly on Chesapeake Bay. Well-stocked with all the things a family will need for a wonderful time and a very responsive manager. Truly an excellent place to stay!
Stayed 3 nights in Nov 2018

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

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

Iris S.

Great Stay!

We had an awesome weekend at this property! The house is very well laid out, well furnished and you can’t beat the views! All in all, a positive experience. We hope to be back some day!
Stayed 3 nights in Dec 2018

10/10 Excellent

Eric M.

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

Week at Watermark

Our week at Watermark was a fantastic getaway. The house and property were spacious, well located, and the owner was responsive to our questions and needs.
Stayed 7 nights in Aug 2021

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

Ellen M.

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

Wonderful stay

The house is large and fit us all nicely. Internet connection was fast! The view and yard were great. We especially appreciated the responsiveness of the manager No complaints—just fun all around
Stayed 14 nights in Jul 2020

10/10 Excellent

samantha e.

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

Fun

It was wonderful
Stayed 5 nights in Aug 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

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

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

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

Seth D.

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

A gem of a vacation

This was the best outing we’ve had all year. The space was perfect, the owners were responsive and respectful of space too. We went for my bday and got everything we needed— space, views, water, comfort. Highly recommend to any and all.
Stayed 3 nights in Mar 2021

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

8/10 Good

Sara W., Linwood

Beautiful house

As a family of eight we all had so much room in this amazing house. The kitchen had everything we needed to cook some great breakfasts. We used the kayaks and went in the pool.
Stayed 3 nights in Apr 2019

10/10 Excellent

Terry Ann C., Bethlehem

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

Great get-away!

The property was perfect for a get-away with family, including two infants. The home was large and well appointed. The pool was clean and well cared for. The owner was very responsive, providing a recumbent bike for my husband to continue his rehab therapy. We had a wonderful time at this beautiful place.
Stayed 7 nights in Jun 2021
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Erin E.

Fabulous house on the Eastern Shore

Book it. This house is huge and has everything you need for a great getaway and we didn't even stay in the summer. We'd love to come back to take full advantage of all this house has to offer.
Stayed 3 nights in Jan 2017

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

Michele D., Philadelphia

Perfect!

Great place to celebrate my 50th! Friends gathered from near & far & easily made your home ours! We made many new memories and laughed so much! Thank you for providing a place to exhale, relax, and rejuvenate!
Stayed 3 nights in Aug 2018

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

Erica R.

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

Perfect Weekend Retreat

Gorgeous property, gracious host and lots of activities for kids. The game room saved us on a dreary rainy day. The pool was great with lots of toys for the kids. Didn’t get the chance to kayak but nice to have them offered. There’s also a pond full of turtles our kids had fun feeding. Plenty of room for everyone to spread out. Would definitely come back!
Stayed 4 nights in May 2021

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

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

Lynn T., Portland, Oregon, USA

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

Great Family Getaway on the Bay

This house was fantastic for our 10 person family reunion. It was accessible for our 91 year old matriarch; had quiet places for our hermit writer; the pool and game room provided plenty of space for our twenty-something cousins and boyfriends. The kitchen/dining room is huge - room for cooking and impromptu dance parties. The dock was a wonderful place to enjoy a breeze and a view of the osprey nests along the bay. Sunsets from the back deck were amazing. We are looking forward to returning.
Stayed 7 nights in May 2019