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Entire home

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Waterfront holiday home with kitchen and patio

Photo gallery for Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Exterior
Interior
Exterior
Interior
Smart TV, fireplace, video games, DVD player
In the heart of Talbot County, this beautiful 4000+ sq. ft. waterfront home welcomes you with its newly furnished interior and expansive water views from multiple rooms. Enjoy relaxing on the large deck, sipping your favorite brew or wine, and take advantage of outdoor grilling and a private pier for fishing, crabbing & kayaking/boating.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 104000 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Fireplace
  • Washer
  • Dryer

Add dates for prices

About this property

Entire place

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

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Talbot County MD Short Term Rental License #STRN-23-12

Arrive at your beautiful, 4000+ sq. ft, 2 story waterfront 5-bdr, 3.5-bth retreat with its own private pier near the historic and charming town of St. Michaels. Enjoy breathtaking waterfront views from the expansive decks, complete with a gourmet grill for al fresco dining and a cozy backyard fire pit perfect for relaxing with a cold brew or glass of your favorite wine. Your private pier awaits you for fishing, crabbing, kayaking and paddle board (all provided)

There are multiple cozy entertainment spaces for your enjoyment. Relax and unwind in the large living room, featuring a large screen TV with high-speed WiFi and 180-degree water views. Enjoy the natural light and serene ambiance of the sunroom, overlooking Oak Creek. Take in the stunning water views from the comfort of the 2nd floor master s sitting area also with a wide screen TV. Retreat to the front reading room of the house for a quiet moment, conversation or to read a book and look out over the serene landscape.

You will be in the most convenient of locations. Just a 2 minute walk to the Oaks Resort with dining and jazz several times a week. Historic St. Michaels is a 5 minute drive with its charming stores, multiple dining venues and the Chesapeake Bay Maritime Museum. Explore the beauty of Oxford and the many activities, unique shops, and restaurants in Easton.

Our Talbot County License #STRN--23-12 permits 10 GUESTS in our house and property at any given time. Please note that our Talbot County Short Term Rental license requires a three night minimum and does not allow any events to be held on the property. We are located in a serene, residential community in Royal Oak and Talbot County has a noise ordinance - no noise after 10 PM No pets permitted.

Highlights
o 5 min drive to historic St. Michaels
o 2 min walk to the Oaks Resort
o beautiful water views
o large deck areas
o private pier for fishing, crabbing & kayaking/boating
o custom coffee & tea bar; complimentary whole bean coffee, grinder, coffee selection
o fully equipped kitchen
o gas fireplace
o outdoor fire pit
o outdoor gourmet(new Weber Genisus) barbecue
o 2 large screen TV, Cable & Disney Channel for the kids
o high speed internet
o game collection box and kids room with DVD's and player
o horseshoes, cornhole, badminton and other games
o fishing rods and tackle box
o TESLA charging port
o 240 v, NEMA EV charging port
o Two main bedrooms - one on first floor and one on second floor with three additional bedrooms and large sitting room with window wall overlooking the water.

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Breakfast available for a fee
  • Chef service
  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Video games

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • 3 steps to reach entrance
  • No lift
  • Smoke-free property

Services and conveniences

  • Concierge services
  • Housekeeping (on request)
  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Arcade/game room
  • Kayak
  • Cycling nearby
  • Fishing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Swimming nearby

Safety features

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

General

  • Electric car charging station
  • Garden
  • Housekeeping (on request)
  • Unit size: 4,000 square feet

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Policies

Check-in

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

Check-out

Check-out before 10:00 AM

Special check-in instructions

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

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Children must be accompanied by an adult over 25.

Events

No events allowed

Smoking

Smoking is not permitted

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 first aid kit
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
Property Registration Number Talbot County Short Term STRN-23-12

We should mention

This property does not have any lifts

About the area

Map
easton, MD

What's nearby

  • Saint Michaels Village - 5 min drive - 5.9 km
  • St. Michaels Winery - 6 min drive - 7.3 km
  • St. Michaels Marina - 7 min drive - 7.9 km
  • Chesapeake Bay Maritime Museum - 8 min drive - 8.6 km
  • 1879 Hooper Straight Lighthouse - 8 min drive - 8.6 km

Getting around

  • Cambridge Station - 30 min drive
  • Easton, MD (ESN-Easton - Newnam) - 17 min drive

Restaurants

  • ‪Stars - ‬9 min drive
  • ‪Foxy's Harbor Grille - ‬8 min drive
  • ‪Carpenter Street Saloon - ‬7 min drive
  • ‪The Crab Claw - ‬8 min drive
  • ‪t at The General Store - ‬10 min walk

Frequently asked questions

Is Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak?

Check-in begins at 4:00 PM.

What time is check-out at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak?

Checkout is at 10:00 AM.

Where is Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak located?

This family-friendly Easton holiday home is located on the waterfront, 3 mi (4.8 km) from Saint Michaels Village, and within 6 mi (10 km) of Chesapeake Bay Maritime Museum and Saint Marys Square. Back Creek Park and Church Cove Park are also within 6 miles (10 km).

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Reviews

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 47 out of 51 reviews
Rating 8 - Good. 3 out of 51 reviews
Rating 6 - Okay. 1 out of 51 reviews
Rating 4 - Poor. 0 out of 51 reviews
Rating 2 - Terrible. 0 out of 51 reviews

Reviews

10/10 Excellent

Barbara S.

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

Wonderful stay

The Chesapeake Landing is a lovely property right on Oak Creek in St Michael's, MD. The house is large, with lots of gathering places. It is well-furnished and well-stocked. It's about a 5 minute drive to downtown St Michael's. We had a wonderful stay!
Stayed 3 nights in Jun 2025

10/10 Excellent

Phil V.

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

beautiful location

wonderful home and great views. Clean, quiet, plenty of amenities
Stayed 3 nights in Dec 2024

10/10 Excellent

Craig S.

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

Wonderful time by the bay

We enjoyed our stay. The home was comfortable and well set up and the owners were wonderful! Would stay again.
Stayed 4 nights in Jul 2022

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is an exceptionally beautiful property with dock access and great views of the water. Check in is super easy, the kitchen is large and very well appointed, the house is large enough for ten people to have alone time in other rooms but cozy enough in the kitchen and great room area to enjoy hanging out together and looking out over the water. About a five-minute easy drive to St. Michael's town and anything else you could need. Games, puzzles, fishing rods, kayaks, some crabbing gear - our group ranges in age from 12 to 85 and there really is something for everyone here. We have stayed at this home for close to a week every summer for the past three years and hope to continue to do so. It's fabulous!
Stayed 4 nights in Jul 2025

10/10 Excellent

Kirsten S., Washingon, DC

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

Best Labor Day Weekend Stay!

The house is even better in person - we had 6 adults, a toddler and 2 babies and the layout and views were absolutely perfect. The owners are incredibly kind, responsive, and welcoming! Would highly recommend this property to anyone looking to enjoy a trip to St. Michaels.
Stayed 3 nights in Sep 2022

6/10 Okay

Carol M.

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

very nice-there should be a wooden or slate walk to dock, grass was high and after the rain very wet

A nice property.
Stayed 5 nights in Jul 2022

8/10 Good

Wendy Y., New York, United States

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

Beautiful place

This is a beautiful house and place for vacation with friends and family. Barbara was very friendly. Just not too many fish and crabs.
Stayed 3 nights in Jul 2022

10/10 Excellent

Mary-Elaine P.

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

A wonderful get-away

Two friends snd I stayed here to celebrate my birthday. It was as beautiful as pictured. We relaxed inside and out. It is SO peaceful. The house is beautifully decorated, yet comfortable. Near the end of our visit I summed it up by saying that it felt like visiting the home of a friend who has good taste. We would love to return and bring our daughters!
Stayed 5 nights in Jul 2023

10/10 Excellent

George R.

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

Wonderful Winter Weekend Getaway!

Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the casual eating area off the kitchen was a great place for our other meals.Because of our timing we were not able to take advantage of the outdoor activities at the house but could certainly enjoy the beautiful view of the creek, made even more picturesque with a fresh coat of snow on the lawn and ice on the water. The location of the house was terrific, with Easton, St. Michael’s, and Tilghman Island all very close by.The consensus of our group was that we would love to come back to this wonderful home—maybe in the summer months to better appreciate all that it’s waterfront location can offer!
Stayed 3 nights in Jan 2025

10/10 Excellent

Eileen M.

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

50th Anniversary family getaway.

This immaculate and tastefully decorated treasure was a wonderful place to celebrate our 50th anniversary with our family. Our out of state daughters and their families gifted us with a long weekend for all of us at this amazing property. There was plenty of room for 10 of us to have space, with enough bedrooms for all and plenty of bathrooms to share. The kitchen and pantry was well stocked and there were a few side rooms for the grandchildren to play. The most special treat were the back decks, the large yard with the dock and view of the water. There were indoor as well as yard games available, a fire pit where we enjoyed s’mores and crab traps and fishing rods. This home did not disappoint. It provided an enjoyable and memorable weekend for all us.
Stayed 3 nights in Oct 2022

10/10 Excellent

Karen and John O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our family stay in this wonderful home with our four adult kids. We kayaked, played corn hole, whiffle ball, card games and watched movies. The Oaks Resort is close but the restaurant is only open Tuesdays through Thursdays to the public. We spent a lot of time in nearby St Michael’s (5 minute drive).The house was well-equipped and the games, sitting rooms and number of rooms were perfect. Would highly recommend!
Stayed 3 nights in Aug 2025

10/10 Excellent

Stephen J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home in excellent condition.Property manager and owner very responsive to any issue.
Stayed 6 nights in Jul 2025

10/10 Excellent

John C.

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

Chesapeake St Michaels

Beautiful property next to The Oaks in Easton/St Michaels, Maryland. A family wedding brought us here and it couldn't have been more convenient. Lovely home on the water. Unfortunately we were so busy we didn't utilize it to it's potential. I highly recommend this property.
Stayed 3 nights in Jun 2025

8/10 Good

Karl F.

Liked: Cleanliness, communication, location, listing accuracy

Great Spot

Rented for extended family for a weekend reunion ( 5 adults 3 kids) End of street location, very quiet, clean and on the water. Close to St Michael’s and Oxford Ferry.
Stayed 3 nights in Jun 2025

10/10 Excellent

Lori S.

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

Family weekend

We absolutely loved your place and it was perfect for our family. We would love to come back and stay next summer!
Stayed 3 nights in May 2025

10/10 Excellent

clay b.

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

Great weekend trip

Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing.
Stayed 3 nights in Oct 2024

10/10 Excellent

Joe w.

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

Wonderful stay at a wonderful home

This property worked perfectly for our family. it was clean, a perfect size for several couples, & the host was a great communicator. We hope to come back again sometime soon!
Stayed 3 nights in Oct 2024

10/10 Excellent

B. Monica M.

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

Comfortable, casual elegance.

This house is wonderful! Property was clean, comfortably furnished, beds were comfortable, kitchen had everything we needed. Our hosts were more than gracious and the property manager was friendly, thorough, and available - our few questions were addressed within an hour. Perfect!
Stayed 14 nights in Sep 2024

10/10 Excellent

Gerard F.

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

Close to Perfection

They say nothing is perfect, but this property was as close to that as we have experienced. The house was clean, comfortable, well equipped, in a great location, and with beautiful surroundings. With five bedrooms, we were able to comfortably accommodate all of our children and grandchildren. There’s plenty of space to spread out and several semi private sitting areas to give anyone their own space if they don’t want to be with larger group. We couldn’t have asked for anything more. Highly recommend this property.
Stayed 3 nights in Aug 2024

10/10 Excellent

Wendy D.

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

Wonderful home

Gorgeous home, very well stocked with so many extras. They have a cabinet that has spices/cooking items galore. Beautiful views of the lake, and paddle board and kayaks provided. The whole family loved it!
Stayed 3 nights in Aug 2024

10/10 Excellent

Verified traveller

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

Beautiful home on a beautiful property

We stayed at this home last year with our extended family and hope to stay again for many summers to come. It is impeccably clean, has many extra amenities, and being able to fish, crab and kayak right from your back yard is very handy and fun for all! Also a quick, maybe 10 minute drive, into St. Michaels - great restaurants and shops and just the right size to walk around for a couple hours. We've had two great vacations in this home and hope for more!
Stayed 4 nights in Jul 2024

10/10 Excellent

Chris B.

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

Convenient to the Oaks

We used this house for a wedding at the Oaks (which is adjacent and therefore very very convenient).
Stayed 5 nights in Jul 2024

10/10 Excellent

Betsy W.

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

Beautiful Waterfront Home

We were in town for a wedding at The Oaks located right next to the road the house is on, so the location was perfect! We enjoyed the outdoor activities (kayaks, paddleboard, etc) in spite of the sweltering heat! And the waterfront views were fabulous! It was also just a short drive to lovely St. Michaels.
Stayed 3 nights in Jul 2024

10/10 Excellent

Pam A.

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

Great home for family event

We were in town for a wedding at Kirkland Manor with our family. Home was close to the venue and very comfortable. We had a 2 yr old with us and home was safe. Really happy that you had access to some grocery items such as spices, foil, toiletries as well as items to use such as kayaks and fishing poles.
Stayed 3 nights in Jun 2024

10/10 Excellent

Lachmayr M.

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

Outstanding

Huge house with beautiful views. Lovely (You will need to sign a lease)
Stayed 3 nights in May 2024