Entire home

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

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Property grounds
View from 2nd flr gathering rm - plenty of seating for all to enjoy serenity!
Front view of your vacation home "Chesapeake Landing"
View from deck - grilling or sipping your favorite beverage or just gazing!
Arrive at your destination and immediately feel good!

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms3+ bathroomsSleeps 10

Popular amenities

  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill
  • Deck or patio

Explore the area

View in a map
easton, MD
  • Place, Saint Michaels Village
    ‪5 min drive‬
  • Place, St. Michaels Winery
    ‪6 min drive‬
  • Place, St. Michaels Marina
    ‪7 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪18 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed

Bedroom 5

3 Single Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Jetted bathtub · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 3

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 4

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area

About this property

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 ensuite bedroom and gathering area with a panoramic view of Oak Creek 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.
o Spaces for gathering and spaces for quiet reflections and/or me time.
Our prices include all fees. No hidden fees.

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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
Children must be accompanied by an adult over 25.
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
NO MORE THAN 10 PEOPLE ARE ALLOWED ON THE PROPERTY AT ANY GIVEN TIME
WE WILL BE EMAILING LEASE FOR YOUR SIGNTURE AND RETURN TO ME TO SECURE YOUR BOOKING/RESERVATION. BARBARA FOCHT - CHESAPEAKE BAY REAL ESTATE PLUS

Important information

You need to know

Property Registration Number Talbot County Short Term STRN-23-12
Property # 2750866vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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

About the area

Easton

Located in Easton, this holiday home is in the city centre and on the waterfront. St. Michaels Winery and Windon Distilling are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chesapeake Bay Maritime Museum and Easton Cycle and Sport. Discover the area's water adventures with kayaking, power boating and fishing nearby, or enjoy the great outdoors with cycling.
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 Museum - 6 min drive - 7.6 km
  • St. Michaels Marina - 7 min drive - 7.9 km
  • Chesapeake Bay Maritime Museum - 8 min drive - 8.6 km

Getting around

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

Restaurants

  • ‪Foxy's Harbor Grille - ‬8 min drive
  • ‪The Crab Claw - ‬8 min drive
  • ‪Carroll's Market - ‬8 min drive
  • ‪Ava's Pizzeria & Wine Bar - St Michaels - ‬7 min drive
  • ‪Doc's Sunset Grille - ‬27 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak?

As of 10 May 2026, prices found for a 1-night stay for 2 adults at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak on 11 May 2026 start from £645, 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.

How much is parking at Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak?

On-site parking is available at the 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).

Reviews

10

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 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

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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
Response from VrboOwner on 2 Jun 2025
We are so happy that you enjoyed your stay at Chesapeake Landing. We look forward to your return visit. bhf
Verified

10/10 Excellent

Katherine H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely property on the Chesapeake Bay. Quiet community-easy drive to St.Michaels. House fully equipped with everything you could want! Good biking area. Highly recommend!!
Stayed 3 nights in Sep 2025
Response from VrboOwner on 14 Oct 2025
We are pleased that you found Chesapeake Landing the perfect place for your stay at the Easter shore and St. Michaels
Verified

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
Response from VrboOwner on 14 Oct 2025
Glad that you found our wonderful home to be your perfect location
Verified

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
Response from VrboOwner on 6 Aug 2023
Our goal is to have our guests enjoy their stay and the comforts of our home. We look forward to you staying with us again soon. Barbara
Verified

10/10 Excellent

Cathy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home and property. Most well equipped kitchen I have seen in a rental home. Excellent location, with only a 5 minute drive to downtown St. Michael's. Stayed at the home for a girls' weekend and several of my friends want to return to the house with their families!
Stayed 3 nights in Sep 2025
Verified

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
Response from VrboOwner on 29 Jul 2025
We thank your kind kind review - we are delighted that you enjoyed your stay and hope you come again.
Verified

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
Response from VrboOwner on 30 Jul 2025
We are glad you enjoyed your stay at "The Landing" and that you liked our many separate gathering spaces. Our convenient location is very much a plus. Please come again. Barbara
Verified

10/10 Excellent

Alex F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as described except for one bedroom’s layout. Fully stocked kitchen, beautiful view, lots of gathering spaces, glorious weather. Boat slip allowed us to bring our own. Wonderful family retreat.
Stayed 3 nights in Aug 2025
Verified

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
Response from VrboOwner on 30 Jul 2025
We are happy you liked our quiet setting and location. We hope you can join us again> Barbara
Verified

10/10 Excellent

Mark M.

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

great place

We were hear for a wedding. We loved the house and location. Perfect venue for us.
Stayed 3 nights in Aug 2023
Response from VrboOwner on 14 Aug 2023
Thank you for taking the time to review our perfect home for your perfect stay.
Verified

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
Response from VrboOwner on 21 Oct 2024
We are pleased you enjoyed your stay at Chesapeake Landing and you found our home floor plan to be ideal for several families. We look forward to your return visit.
Verified

10/10 Excellent

Anita W.

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

Just the Spot for a Family Celebration

Gorgeous location, spacious, comfortable and well-appointed home with delightful views and plenty to do. We all had a great time celebrating a 60th wedding anniversary!
Stayed 6 nights in Aug 2022
Response from VrboOwner on 6 Aug 2023
We are glad you enjoyed our spacious home that is great for family times togethers with its separate spaces, open spaces and quiet views.
Verified

10/10 Excellent

Kirsten S.

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
Response from VrboOwner on 6 Aug 2023
Our floor plan is ideal for multiple families giving private and open spaces for all to enjoy our waterfront home in the unique Hamlet of Royal Oak.
Verified

10/10 Excellent

Niki H.

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

Wonderful stay

We stayed here with a group of friends including our younger kids. The place was wonderful. It was clean and had everything we needed. The location was excellent and the owners/property manager were responsive. We highly recommend this place.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 6 Aug 2023
We are pleased that our home fit all your needs and you had a wonderful stay. We hope you make Chesapeake Landing your place to stay in St. Michaels..
Verified

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
Response from VrboOwner on 28 Sept 2024
We like that we are convenient to The Oaks wedding venues. We hope you can come back again to enjoy St. Michaels!
Verified

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
Response from VrboOwner on 6 Aug 2023
We are glad you thought our property and home was very nice. We pride ourselves in offering our guests more than they expect in features and amenities while keeping with the character of the eastern shore.
Verified

8/10 Good

Wendy Y.

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
Response from VrboOwner on 6 Aug 2023
We are glad you enjoyed our lovely house for your vacation. We hope you spend your next stay in St.Michaels with us.
Verified

10/10 Excellent

william v.

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

Great house

The house was really nice with all the necessary amenities. Plenty of differant areas to hang out and nice bedrooms. Out side view of the water was great.
Stayed 3 nights in May 2023
Response from VrboOwner on 6 Aug 2023
We are so happy to have our guests enjoy this wonderful home on the Eastern Shore of MD.
Verified

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
Verified

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
Response from VrboOwner on 12 Aug 2025
We are happy you enjoyed our property wit its many separate spaces for guests to enjoy. We hope you will stay as our guest again.
Verified

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
Verified

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
Response from VrboOwner on 28 Sept 2024
We are delighted when "the whole family loved it". We look forward to your return in the future.
Verified

10/10 Excellent

Beth W.

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

Acorn Rd

An amazing time , fabulous house, with room for everyone. the kayaks paddle board and multiple games for all ages made every day fun.
Stayed 5 nights in Jun 2022
Response from VrboOwner on 6 Aug 2023
y
Verified

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
Response from VrboOwner on 28 Sept 2024
So glad you enjoyed the size and delicious views from Cheapeake Landing. We hope you will come again soon.
Verified

10/10 Excellent

Anastasia L.

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

Labor weekend

The house is absolutely beautiful! It has everything what you need for your comfort stay! Kitchen is very well equipped! We enjoyed kayaking, fishing and sitting around fire pit at the evenings. We will definitely come back!
Stayed 3 nights in Sep 2023
Response from VrboOwner on 19 Sept 2023
So glad you loved our home as much as we do - We welcome your return. bhf

About the host

Hosted by Barbara H Focht

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