Our Always Dreaming Cottage - The Bay At Your Back Steps

Top rated by guests
The Bay is our backyard.
Half bath, downstairs
Master bath for first master
Walk right out to the waters edge, shallow depth
The expanse of beach to our right, creates a natural cove
review stars
9.7Outstanding
(154 Ratings)
Guests loved the perfect location right on the beach with amazing views, comfortable beds, clean property, and peaceful neighborhood. They enjoyed the private beach, well-equipped kitchen, and friendly hosts, making it a memorable vacation.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.7 / 10
Outstanding(154 Ratings)

Cottage in Maryland

4 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area

About this cottage rental

Welcome to The Aways Dreaming Cottage with two bedrooms which sleeps four (4) – where dreaming is a pastime you will enjoy. There is not another cottage with this Bay access and two level decks, for these multi-walking miles of beach front. Our cottage is a privately-owned Chesapeake Bay front home only steps from the water’s edge. Located just 50 mins from Washington, DC, 14 miles north of the quaint seaport village of Solomons Island and 40 minutes south of Maryland’s capitol of Annapolis, the Always Dreaming Cottage at Kenwood Beach will relax you with quiet walks on the beach, fossil, shark tooth and sea glass collecting and best of all the lull of lapping waves as you enjoy the sunsets on the water’s reflection.
Don’t fight the bridge traffic, come enjoy all the Chesapeake Bay has to offer on the Western Shore!
During your week stay with us enjoy nearby Calvert Marine Museum, Calvert Cliffs, Flag Pond, craft, flea and antique malls, concerts of mainline stars in intimate venues or local wineries and evening music entertainment. Prefer quiet afternoons? Enjoy a book on the back deck, track marine traffic as it steams by or sun bathe on the master suite’s private deck on the second floor of our Always Dreaming beach side cottage.
If you enjoy kayaks and swimming our calm bay waters are inviting you to visit our shores. One of the few Bay coastlines where you can walk for several miles, this section of the Chesapeake Bay Western shore is an uncrowded wonderland. If you enjoy fishing or crabbing, our private community dock is only steps away from our house. Amenities such as restaurants and grocery shopping are nearby for your convenience either north to Prince Frederick or South to Lusby/Solomons Island.
Our Always Dreaming Cottage is a two bedroom, two and a half bath home, with a fully equipped kitchen and gas barbecue grill. The owners are in the neighborhood easily available if a need arises or for suggestions of local activities of interest. We are a water conservative community and household, so showers only and no baths. The home does not have a dishwasher or washer/dryer at this time. There is a local laundromat. Sheets, bath and beach towels can be provided for a small additional charge or you may bring your own. The master suite has a queen-sized bed. The second bedroom has a full-size new bed with a private bath. The house is limited to four adults maximum occupancy. Bring your own water sport toys, sand castle building sets, kayaks, etc. to enjoy your time with us at the Always Dreaming Cottage.




Amenities

Non-smoking
Pets allowed
Family friendly

Map of Maryland

city location on map

Ratings and reviews

9.7 / 10
Outstanding(154 Ratings)
review starsSummary of reviews
Guests loved the perfect location right on the beach with amazing views, comfortable beds, clean property, and peaceful neighborhood. They enjoyed the private beach, well-equipped kitchen, and friendly hosts, making it a memorable vacation.
From real guest reviews summarized by AI
10 / 10Outstanding·Jul 2026
Great property and great host. Would stay here again!
8 / 10Excellent·Jul 2026
Things were clean at the cottage and the view and location is perfect, just a few steps away from the bay.However the listing states access to the pier which you do not have and the hot tub is one of the old type jacuzzi tubs but that didn’t bother us as we don’t like them.It was nice having a bathroom on each floor.I would suggest the mini splits be cleaned. They were very dirty and the one in the bedroom with sliding doors had to be set as low as it would go in order to keep the room cool.When you pull into the property it is not inviting as there are lots of weeds, a car under a cover and just not pretty at all.The front porch looking out at the bay is very nice and where we spent a lot of our time although some weeds could be taken care of.Robert was very nice to deal with as well.Overall we thought it was clean and served our purpose well. You just can’t beat the view and location to the bay. We enjoyed our stay very much!
10 / 10Outstanding·Jul 2026
The property was as showed peaceful and great for dog owners never barely anyone on beach
6 / 10Average·Jun 2026
Upon arrival at check-in (4:00pm), the owner was at the house stating he had been running late, and remained for an hour doing laundry. The house had not been cleaned - dirt, food, sand, dog hair visible everywhere, and outdoor trash cans full. Bathrooms and kitchen not cleaned including, femine products in one of the bathroom trash cans. Fortunately, we brought our own towels and sheets as the ones provided had stains from previous use. Additionally, while checking-in, we noticed the AC in one of the upstairs bedrooms was not functioning. It was blowing, but not cool air. We notified the owner who came back to investigate. He attempted to insist it was cooling properly which I stated it was not. There was an error code which he stated he would review and get back with us. We followed up with texts and emails over the next two days regarding several other issues including the AC. We received responses on the other issues but never on the AC issue. We finally discovered on the last night of the week, if you do not run the downstairs AC unit, the bedroom will then cool sufficiently, i.e., you cannot use both at the same time. On a related note, the filters on all three split unts are black and full of dirt. The VRBO listing description of the house identifies use of the community pier. Access to the pier does NOT exist. The only redeeming qualities of this house is location and views.

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Our Always Dreaming Cottage - The Bay At Your Back Steps. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Our Always Dreaming Cottage - The Bay At Your Back Steps pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Our Always Dreaming Cottage - The Bay At Your Back Steps?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.


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