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Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

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December 2024
January 2025

Photo gallery for Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Beach
Fridge, microwave, oven, stovetop
Property grounds
4 bedrooms, desk, iron/ironing board, free WiFi
Exterior

Reviews

10 out of 10

Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 8511 sq m

Popular amenities

  • Washer
  • Barbecue grill
  • Pet-friendly
  • Outdoor space
  • Parking available

Explore the area

Map
St. Michaels, MD
  • St. Michaels Winery
    7 min drive
  • Chesapeake Landing Restaurant
    3 min drive
  • Cambridge Station
    46 min drive
  • Annapolis, MD (ANP-Lee)
    81 min drive

Room options

About the area

St. Michaels

On waterfront.Within 6 miles (10 km) of this vacation home, you'll find Chesapeake Bay Maritime Museum and St. Michaels Museum. St. Michaels Winery is within 6 miles (10 km) and Phillips Wharf Environmental Center is within 12 miles (20 km).
View more Vacation homes in St. MichaelsOpens in a new window

What's nearby

  • St. Michaels Winery - 7 min drive
  • St. Michaels Museum - 7 min drive
  • Chesapeake Bay Maritime Museum - 7 min drive
  • Avalon Theatre - 24 min drive
  • U.S. Naval Academy - 78 min drive

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 27 min drive

Restaurants

  • ‪Foxy's - ‬7 min drive
  • ‪Chesapeake Landing Restaurant - ‬3 min drive
  • ‪Blue Crab Coffee Co. - ‬6 min drive
  • ‪Carpenter Street Saloon - ‬6 min drive
  • ‪The Crab Claw - ‬7 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Luxury Waterfront with pool and deep water dock, minutes from St Michaels.

Licensed by Talbot Co MD STRN-23-11. Mimimum 7 night reservations only - Sat to Sat. Our property is ideally suited for family style vacations, so the owners only permit bookings where responsible adults are responsible for supervision of our guests, we do not accept reservations from groups where this condition is not met. We are a luxurious mini estate five minutes from St. Michaels, we book Saturday to Saturday vacations or month long holidays, this property features a traditional Eastern Shore telescope house with formal living and dining rooms, family room and large eat-in kitchen having Italian tile flooring and all Kitchen Aid stainless appliances. The house is comfortably furnished with English and Asian antiques An organic veggie garden, swimming pool and waterfront patio overlook the deep water cove which offers a tranquil water view and a variety of waterfowl both summer and winter. Two seater Kayak, crab pots and fishing rods on property for guests.

Property manager

William A. (Bill) Cree

Languages

English

Property amenities

Pool/Spa

  • Private pool
  • Outdoor pool

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking
  • Car recommended

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Electric kettle
  • Paper towels
  • Spices
  • Blender

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 4 bathrooms
  • Shower
  • Shampoo
  • Outdoor shower
  • Towels provided
  • Hair dryer
  • Toilet paper
  • Soap

Living spaces

  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service
  • DVD player
  • Music library
  • Stereo
  • Books
  • Games

Outdoor areas

  • Patio
  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Telescope

Laundry

  • Washing machine and dryer

Work spaces

  • Printer
  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • Pet friendly
  • 1 total (up to 50 lbs per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • On the waterfront
  • In a rural location
  • Near a health or beauty spa
  • Near a hospital
  • Near outlet shopping
  • Near the bay

Things to do

  • Fitness facilities nearby
  • Water sports equipment
  • Kayak on site
  • Birdwatching nearby
  • Winery tours nearby
  • Hunting nearby
  • Kayaking nearby
  • Horse riding nearby
  • Hiking nearby
  • Cycling nearby
  • Marina nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 5500 sq ft (511 sq m)

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • Note from host: kitchen, family rm. crate required if unattended

Children and extra beds

  • Children are welcome.
  • Note from host: parents are responsible for safty

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
Onsite parties or group events are strictly prohibited
Note from host: up to 12 guests maximum allowed on property
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. Note from host: up to 12 guests maximum allowed on property For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

Luxury Home Deep Water Dock Minutes St Michaels House
Luxury Home Deep Water Dock Minutes St House
Luxury Home Deep Water Dock Minutes St Michaels
Luxury Home Deep Water Dock Minutes St
Luxury Waterfront Deep Water Dock Minutes St Michaels House
Luxury Waterfront Deep Water Dock Minutes St House
Luxury Waterfront Deep Water Dock Minutes St Michaels
Luxury Waterfront Deep Water Dock Minutes St
Luxury Home With Pool Deep Water Dock Minutes From St Michaels

Luxury Waterfront with pool and deep water dock, minutes from St Michaels. Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 24 out of 24 reviews" "
Rating 8 - Good. 0 out of 24 reviews" "
Rating 6 - Okay. 0 out of 24 reviews" "
Rating 4 - Poor. 0 out of 24 reviews" "
Rating 2 - Terrible. 0 out of 24 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

David A.

Liked: Cleanliness
Contented in Content
This HOME is in a beautiful location overlooking a tranquil cove. The house is superbly maintained and is fully equiped with everything you could need for a vacation home. The pool was wonderful on hot summer days. The location is ideal for quick access to all the restaurants and museums in the St. Michaels area. The owner went above and beyond to make us feel welcome and to ensure we had eveything we could wish for and even made Maggie (our Goldendoodle) feel spoiled! We had two wonderful weeks at “Content”, and we left very contented and wishing we could have stayed longer. We look forward to visiting again.
Stayed 14 nights in Jul 2024

10/10 Excellent

Ingrid D.

Liked: Cleanliness
Perfect waterside oasis!
This house is pristinely maintained inside and out. She has done an amazing job anticipating anything a guest could need. The kitchen had all the essentials to cook great meals. The beds were comfy. The pool was perfection! Really can’t find a thing to complain about! (And I’m picky!!)
Stayed 7 nights in Jul 2024

10/10 Excellent

Joe D.

Liked: Cleanliness
Highly recommend
Having traveled to the area several times, we were looking for a special venue for a family gathering. Fortunately, we were able to book The Content for a week. The pictures don’t do justice to this lovely home and terrific setting, and the owner could not have been more welcoming. Highly recommend and hope to return soon!
Stayed 7 nights in Jul 2023

10/10 Excellent

Rhonda P.

Liked: Cleanliness
Perfect family getaway
Lovely, well-maintained, well-stocked, air conditioned house, sited on a huge, flat green lawn by the water. One bed/bath downstairs; 3 bedrooms/2 baths up. Having a pool was delightful, particularly because it was so hot the week we were there. One caveat: the pool is not fenced. The toddler with us was unable to open doors to the outside and we 6 adults were vigilant, so the pool did not present any issues. Wouldn't hesitate to return to this terrific place!
Stayed 7 nights in Jul 2023

10/10 Excellent

David B.

Liked: Cleanliness
Great private spot
Great private property Nice hospitable owner Very nice pool, view and grounds and dock
Stayed 6 nights in Jun 2023

10/10 Excellent

emily d., Washington, DC

Liked: Cleanliness
Christmas at Content
Finely appointed and clean estate in St. Michaels. We had everything we could have wanted and then some for our family stay. Comfy living with beautiful views of the creek and a lawn for the kids and pup to play. We enjoyed the fireplace and kitchen amenities, and the host provided a lovely welcome basket for our arrival. Can't wait to visit again!!!
Stayed 4 nights in Dec 2022

10/10 Excellent

Melanie H.

Liked: Cleanliness
A+ in Saint Michaels
The house is incredible and every aspect of the trip was flawless. The home is incredibly warm, beautifully decorated, cozy, comfortable and completely stocked with everything you could possibly need. The back yard and view of the water is magnificent. I cannot say enough good things about this experience and we hope to come back again!
Stayed 3 nights in Nov 2022

10/10 Excellent

Jenny W.

Liked: Cleanliness
Beautiful home!
My family spent a week at Mandy’s gorgeous property. She was a caring and thoughtful host, and the home was even more beautiful than the pictures reveal. A total gem. The location was a short drive into town and close to Easton as well. We had a wonderful stay and would highly recommend!
Stayed 7 nights in Aug 2022

10/10 Excellent

Kathy D.

Liked: Cleanliness
Wonderful Family Vacation at Content
Our family had the great pleasure of spending a relaxing week at this glorious house in St Michaels. The property is amazing, both inside and out. Beautifully decorated and comfortable rooms, fully equipped kitchen, fantastic salt water pool and serene water views. Mandy, the property owner was so welcoming and generous, after inquiring about what we would like to have on had to drink that first day left us a nice sampling of wine and beer along with snacks. Our days were spent in and around the pool enjoying the comfortable chaise lounges, umbrellas and comfy towels that were on hand for our use. Abundant water birds soaring overhead and hummingbirds flitting about the feeders were a joy to watch. In the evenings we sat on the Adirondack chairs gazing up at the numerous stars that can be seen in the night sky here. We could not have picked a better spot for our family vacation this year. We will have many wonderful memories of our time spent at Content.
Stayed 7 nights in Aug 2022

10/10 Excellent

Elizabeth B.

Liked: Cleanliness
Two weeks of sheer heaven at Comfort.
My husband, daughter and her husband and two children had a wonderful vacation in this beautifully furnished house. The owner could not have been more pleasant, accommodating or generous in seeing to it that we had a great stay. The salt water swimming pool is large and the water stays at a nice temperature during the day and evening. We love kayaking and had many fun paddles on Broad Creek. We enjoyed eating meals on the screened porch with its view of the water and the delightful antics of the hummingbirds who came to get nectar from the feeders just outside. We would return to Comfort in a heartbeat.
Stayed 14 nights in Jul 2022

10/10 Excellent

Lisa B.

Liked: Cleanliness
Perfect spot for a family vacation!
Such a lovely house and property, with wonderful attention to detail. Plenty of room to gather, with cozy spots to go take a break from the action, too. And the views! Perfect for a family gathering.
Stayed 14 nights in Jul 2022

10/10 Excellent

Catherine G.

Liked: Cleanliness
Tranquility
The house and setting was amazing!
Stayed 7 nights in Jul 2022

10/10 Excellent

wendy m.

Liked: Cleanliness
Wonderful stay at Content
Our stay at Content far exceeded our expectations. Mandy, the property owner, was communicative and so friendly from check in to check out. Property was pristine, with every comfort you could want. We have been staying at the Eastern shore for 10 years now and I can easily say the best home I have stayed in. It was so hard to leave!
Stayed 7 nights in Jul 2022

10/10 Excellent

Nena M.

Liked: Cleanliness
Wonderful Vacation
Everything about our stay at this property was wonderful. The house is immaculate and has everything you could possibly need to feel comfortable and enjoy a relaxing vacation. The view was serene, with almost no boat traffic. The large, flat yard and the pool were a big hit with our kids and our dog. We loved having access to the garden for fresh herbs and it was wonderful to be able to bring our dog on vacation with us. Mandy was an excellent host and we will definitely come back for another visit soon!
Stayed 7 nights in Jun 2022

10/10 Excellent

Skip S.

Liked: Cleanliness
Absolutely Wonderful!
We chose this property for our family vacation this year; there were 8 of us altogether, 2 of whom are children. Everyone absolutely loved the home-- it truly felt like a home away from home--and enjoyed our stay, even the 11 year old! The property is private, with lots of grass for playing and running outside. The view is amazing and so peaceful. We felt as if we were at a resort when we were on the back patio and pool area with wonderful padded chaise lounges, umbrellas, and towels. The owner is definitely the hostess with the mostest, having thought of every need one may have and making the entire experience luxurious and comfortable. We will be back.