Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

Photo gallery for Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

A building entrance with a wooden facade, a central door, and two illuminated lantern-style lights on either side.
A spacious room with a large bay window overlooking the sea, a cozy seating area with two armchairs, a dining table, and a ceiling skylight.
A view through a large arched window overlooking a body of water with a distant ship and a rocky shoreline.
A sunset over a calm sea with chairs and a table on the shore.
A dark wooden front door with a white and purple trim, a small window above it, and a lantern above the door.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Discover nearby landmarks
    Near Chesapeake Bay

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Washing machine

Explore the area

View in a map
Stevensville, MD
  • Place, Northern Chesapeake Bay
    ‪1 min walk‬
  • Place, U.S. Naval Academy
    ‪33 min drive‬
  • Place, Annapolis City Dock
    ‪36 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪64 min drive‬

Rooms & beds

2 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Living Room 1

2 Double Sofa Beds

3 bathrooms

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

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

Spaces

Deck or patio
Kitchen
Number of living rooms
Outdoor play area
Garden
Dining area

Add dates for prices

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Outdoor seating area
WATERFRONT right on a BEACH
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  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, (57 reviews)
WATERFRONT right on a BEACH

About the area

Stevensville

Located in Stevensville, this cottage is on the waterfront. Hammond-Harwood House and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and some of the area's activities can be experienced at Queenstown Harbor Golf and Bay Hills Golf Club. Looking to enjoy an event or a game while in town? See what's happening at Alumni Hall or Navy-Marine Corps Memorial Stadium.
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Map
Stevensville, MD

What's nearby

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • Chesapeake Bay Bridge - 20 min drive - 20.7 km
  • U.S. Naval Academy - 33 min drive - 34.2 km
  • Navy-Marine Corps Memorial Stadium - 34 min drive - 35.2 km
  • Annapolis City Dock - 36 min drive - 35.9 km

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 33 min drive

Restaurants

  • ‪Chick-fil-A - ‬12 min drive
  • ‪McDonald's - ‬9 min drive
  • ‪McDonald's - ‬12 min drive
  • ‪Starbucks - ‬13 min drive
  • ‪Hardee's - ‬11 min drive

Frequently asked questions

Is Chessie Cottage-Chesapeake Bay Great views from easy single floor living! pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much does it cost to stay at Chessie Cottage-Chesapeake Bay Great views from easy single floor living!?

As of 30 Oct 2026, prices found for a 1-night stay for 2 adults at Chessie Cottage-Chesapeake Bay Great views from easy single floor living! on 10 Apr 2027 start from £1,462, 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 Chessie Cottage-Chesapeake Bay Great views from easy single floor living!?

On-site parking is available at the property.

What time is check-in at Chessie Cottage-Chesapeake Bay Great views from easy single floor living!?

Check-in begins at 4:00 PM.

What time is check-out at Chessie Cottage-Chesapeake Bay Great views from easy single floor living!?

Checkout is at 11:00 AM.

Where is Chessie Cottage-Chesapeake Bay Great views from easy single floor living! located?

Situated on the waterfront, this cottage is steps away from Chesapeake Bay and Northern Chesapeake Bay. Matapeake State Park is 2.3 mi (3.7 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 16 out of 16 reviews
Rating 8 - Good. 0 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved our stay at Chessie Cottage. Great location and such beautiful and comfortable retreat on the water. A great weekend get away.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was probably one of the best houses we ever have rented. It’s absolutely stunning.
Stayed 2 nights in Oct 2026
Response from VrboOwner on 11 Oct 2026
Thank you! That means a lot to us! Please come again.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Water front beautifulHosts were wonderful and availableExtremely dog friendly
Stayed 17 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent, peaceful, quiet, eclectic, property. Enjoyed by all, including our dog Gunther. We went to Kent Island for the crabs, and enjoyed a great time in Annapolis for Admiral’s Day. It was a very relaxing weekend in a wonderful place.,
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Chessie Cottage was one of the most enjoyable and comfortable VRBO rentals we’ve ever had. We couldn’t have been happier. The cottage is tastefully decorated and immaculate. The water views are vast, beautiful, and serene. We simply cannot say enough about this rental. We absolutely loved our stay.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nic experience all around
Stayed 4 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing cottage — beautiful views, very comfortable rooms with great attention to detail, amazing kitchen for those who like to cook. Bonus was that it’s pet-friendly. A great place to relax, retreat, feel cozy in the fall weather.
Stayed 7 nights in Oct 2025
Verified review

10/10 Excellent

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

Love the Chessie Cottage!

This was our 3rd time staying at the Chessie Cottage and it was another great experience. We love everything with the home and enjoy every minute watching the ships pass by and the amazing sunsets. Can’t wait for our next visit!
Stayed 7 nights in Jun 2025
Response from VrboOwner on 30 Jun 2025
Karen and John, thanks so much for choosing our Cottage for another peaceful getaway! We appreciate you and can’t wait to see you again!
Verified review

10/10 Excellent

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

Spectacular property

We had an amazing weekend. Great location right on the Chesapeake Bay with amazing sunset views. A very tranquil setting. Loved sitting in Adirondack chairs watching the birds and boats passing by. The house was beautiful inside and out and had every possible amenity you can think of. Hope to be back for another visit soon.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Cute Cottage on the water

We absolutely loved our stay at this cottage! It had everything you could possibly think of - so many thoughtful extras and incredible attention to detail. The hosts truly anticipated every need. The view from the back porch was stunning and the perfect spot to start each morning with a cup of coffee or tea. We didn’t bring our dog this time, but the space was so pet-friendly that we’ll definitely bring him along next time. Highly recommend!
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay at Chessie Cottage, from booking, through checking out. The owners greeted us and gave us a tour….we have rented homes on the Chesapeake for almost 20 years and this was the best greeting we have ever had; they were warm, welcoming and helpful. The home is stunning, completely stocked, and comfortable. The view…..amazing! The host, Janet, also went out of her way to make our stay wonderful. We highly recommend this home and the host. We will be back! Elizabeth, Kevin, and our dog Rocky.
Setting sun reflection on home.
Sunset view from home.
Breathtaking sunset!
Just a beautiful day and view.
Stayed 6 nights in Oct 2025
Response from VrboOwner on 5 Nov 2025
Thanks so much Elizabeth, Kevin and Rocky. We are all so glad that you stayed at the Cottage and hope that you visit us again. Thanks for the wonderful review! Kindly, Janet
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was beyond prepared for our stay including eggs and bacon as well as many other snack items. It beautifully decorated and very comfortable.The out door seating areas on the porch and lawn are great for viewing ships on The Chesapeake. 10 minutes from anywhere you need to be. Little touches like labels helping you find whatever you need and navigating the wall switches for lights and ceiling fans.We loved our mornings with coffee on the porch and evenings with cocktails.So much more could be said, but this is a fantastic property and it made our stay far better than if we had used the hotel.
Stayed 2 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location. Had wedding nearby. Stayed with 2 friends. We each had own bedroom or bed as well own bathroom. Couldn't have been better. Beautiful long weekend, sat outside and watched the sun set. Saw a Great Blue Heron and Eagle Hawk in the back yard. Well equipped kitchen , owner thought of everything. Visited Annapolis, about a thirty minute drive. Also visited a nice walking trail which was about a10 minute drive from house. Definitely would recommend.
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Checking in was easy and the manager, Janet, met us and went over everything. There was a detailed notebook explaining how to work everything and house rules. The open kitchen was beautiful and stocked with everything we could possibly need. In the frige, there were eggs, butter, and other snacks. A welcome basket of chocolates was also there. The appliances were all brand new.
This was one of several beautiful sunsets viewed from the back yaard
A blue heron came often to visit the backyard.
Another sunset viewed from the living room.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Words aren't enough....a picture is worth a thousand words. The adages are true, until Chessie Cottage. You have to BE there to believe it. We have been renting houses up and down the east coast for over 30 years and not by any choice of our own, have sort of become vrbo snobs! Never has a place tickled all of our fancies until this one. There is quite honestly nothing the hosts haven't thought of for one's comfort and artistic pleasure, and neither is there a more peaceful spot on the coast to while away a day, a week, or whatever your heart desires. We have found our unicorn and struggled to pack up and leave. Thank you for making our stay picture perfect for us and the fur baby.
Stayed 8 nights in Oct 2025
Response from VrboOwner on 30 Nov 2025
We thank you for staying and for your kind words! Hoping to see you again at the Unicorn Cottage!
Verified review

10/10 Excellent

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

Absolute Perfection

My husband and I and our little pup Bree stayed for a long weekend - and from start to finish everything about this cottage was just amazing. EVERY amenity is there and thoughtfully provided - you want coffee? It's there with little mug hats to keep it warm as you sit and watch the boats go by - you feel a chill? There’s cozy blankets for the beds AND pup - even beds, bones and toys for Bree. If you think of something you need - trust me they already thought of it and it's there for you to use. And now - the VIEWS!!! I can't even describe how beautiful - rating how beautiful the sunsets each night was our pastime. And the house itself is wonderful - so warm and inviting - modern but uniquely eclectic and cozy - and when you're inside it feels much larger because of the high ceilings and massive windows that give views throughout the house end to end. This is where you want to be on Kent Island - I'll never go anywhere else.
Stayed 3 nights in Oct 2024
Response from VrboOwner on 15 Oct 2024
Thank you Kim for the wonderful review! Looking forward to your next stay!😘
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