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Our Always Dreaming Cottage - The Bay At Your Back Steps

Beachfront cottage for sun and fun

Photo gallery for Our Always Dreaming Cottage - The Bay At Your Back Steps

The Bay is our backyard.
Double decker on the beach!
Steps to the beach
Walk right out to the waters edge, shallow depth
Lower deck with pier to our community pier

Reviews

9.8 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 4115.2 sq m

Popular amenities

  • Beach view
  • Fireplace
  • Barbecue grill
  • Laundry

Explore the area

View map
Port Republic, MD
  • Place, Matoaka Beach
    ‪7 min drive‬
  • Place, Flag Ponds Nature Park
    ‪8 min drive‬
  • Place, Battle Creek Cypress Swamp Sanctuary
    ‪8 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

1st Master Bedroom

1 Queen Bed

2nd Master Bedroom

1 Double Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 1

Toilet

Bathroom 1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

Our Always Dreaming Cottage - The Bay At Your Back Steps

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.



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Amenities

Kitchen
Pet-friendly
Air conditioning
Laundry
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed
With prior agreement w/owner
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Pets

Pets allowed
Please provide info on pets in order to be approve
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Smoking

Smoking is not permitted
Outside only on driveway and not on deck, thanks

Check-out instructions

The host requires you to complete the following before checking out:
Strip any used beds and gather used towels
Remove personal items and take out the rubbish
Turn off the lights, lock the doors and return the keys
Thank you very much. Drive carefully. Robert
Failure to complete these may result in a negative review from the host.
It's our home and not a motel, please enjoy this awesome beach location and we hope you love it as much as we do.

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
Parties and events are allowed on site
Note from host: With prior agreement w/owner
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

Port Republic

Located in Port Republic, this cottage is on the beach. The area's natural beauty can be seen at Battle Creek Cypress Swamp Sanctuary and Calvert Cliffs State Park, while calvART Gallery and Annmarie Sculpture Garden and Arts Center are cultural highlights. R&J's PlayPark and Calvert Marine Museum are also worth visiting. Discover the area's water adventures with snorkelling and rafting nearby, or enjoy the great outdoors with hiking and ecotours.
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Map
Port Republic, MD

What's nearby

  • Matoaka Beach - 7 min drive - 6.9 km
  • Flag Ponds Nature Park - 8 min drive - 9.6 km
  • Battle Creek Cypress Swamp Sanctuary - 8 min drive - 10.4 km
  • R&J's PlayPark - 8 min drive - 10.7 km
  • Calvert Cliffs State Park - 12 min drive - 16.7 km

Restaurants

  • ‪McDonald's - ‬10 min drive
  • ‪Foster's Grille Prince Frederick - ‬10 min drive
  • ‪Dunkin' - ‬9 min drive
  • ‪Vera's White Sands Beach Club - ‬17 min drive
  • ‪Wendy's - ‬9 min drive

Frequently asked questions

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

Yes, pets are allowed at this property.

How much is parking at Our Always Dreaming Cottage - The Bay At Your Back Steps?

On-site parking is available at the property.

What time is check-in at Our Always Dreaming Cottage - The Bay At Your Back Steps?

Check-in begins at 4:00 PM.

What time is check-out at Our Always Dreaming Cottage - The Bay At Your Back Steps?

Checkout is at 11:00 AM.

Where is Our Always Dreaming Cottage - The Bay At Your Back Steps located?

Nestled on the beach, this Port Republic cottage is just steps away from Chesapeake Bay and Northern Chesapeake Bay. Matoaka Beach and Long Beach are also within 6 miles (10 km).

Reviews

9.8

Exceptional

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy
Rating 10 - Excellent. 121 out of 138 reviews
Rating 8 - Good. 14 out of 138 reviews
Rating 6 - Okay. 1 out of 138 reviews
Rating 4 - Poor. 1 out of 138 reviews
Rating 2 - Terrible. 1 out of 138 reviews

Reviews

10/10 Excellent

adam d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very pet friendly, well equipped, perfect location for fossil hunting.The owner is easy going and attentive. We've stayed here numerous times and have never been disappointed.
Stayed 5 nights in Sep 2025

10/10 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location of the property was excellent. You couldn't get any closer to the Chesapeake Bay.
Stayed 4 nights in Sep 2025

10/10 Excellent

Anthony A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a wonderfully peaceful few days! Our stay was quiet and it was a great pleasure to be so close to the beach and water. I expect we will be coming back soon.
Stayed 5 nights in Aug 2025

10/10 Excellent

Kate B.

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

Amazing stay

This was our 2nd trip and we cannot say enough about how great this palce is! The host Robert is great to communicate with and truly you cannot beat the location. We will surely return for another stay!
Stayed 8 nights in Jun 2025

10/10 Excellent

Daniel S.

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

Stay on the Bay

Right on a private beach, this property offers amazing views, long expanses of beach, comfortable room for four, with a well appointed kitchen and three levels of deck overlooking the water. We had a wonderful time!
Stayed 4 nights in Jun 2025

10/10 Excellent

Annette S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thank you Robert! We had an amazing time at this beach cottage, we had fantastic weather the house is packed with everything you need, big plus on our Shepherd coming along to swim with us. We brought along 2 paddle boards and a tube. We walked the beach line every night and found plenty shells and shark teeth. It’s simply breathtaking, I found a wonderful place to come back to, which I have plans for Labor Day. The double deck was great! Thank you for having us. You have been a great host! Hope we can meet you next time! Jeff said he got a chance to which was wonderful:)
Stayed 4 nights in Jul 2025

10/10 Excellent

seth v.

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

New Family Tradition

This is our second time staying here. We loved it so much, we came back a second time and this has turned into a family tradition each year. The private location on the beach is unparalleled on the bay. We all had fun playing on the beach, looking for shells and sharks teeth and just taking walks. Even the storms are magnificant at this location.We found some nice size shark teeth this time and also learned that this area was likely a megalodon nursery. The only thing that did not go well was fishing. We did not catch a single fish all week. Lots of crabs but no fish. We need to learn when they come through later in August and September maybe to do a little better.
Stayed 8 nights in Jul 2025

10/10 Excellent

Amy C.

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

Loved the location, a bit of everything

This was a perfect spot and cottage for our needs. Sharks teeth and shell hunting right off the deck, beach walking, fishing from a pier, awesome deck to relax. We loved it for our short getaway!
Stayed 3 nights in May 2023

8/10 Good

Susan H.

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

Great location, but…

We have stayed in this cottage several times and truly love the location. It is showing signs of wear and tear and needs some upgrading to justify the price.
Stayed 4 nights in Oct 2024

10/10 Excellent

Vickie B.

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

Location! Location! Location!

This home cannot be beat when it comes to location. Deck is literally only a few steps to the Chesapeake Bay. Watch dolphins, skates feeding, osprey fishing, and eagles soaring all day long. Watch ships from all over the world coming to and from Baltimore Harbor. Hours and hours of beach combing for shark teeth. We found quite a few- one especially large Mako shark tooth.The cottage is clean, though keep in mind it is an older dwelling. Well equipped. We needed for nothing during our stay. Tastefully decorated and very comfortable beds. Sunrise from the front bedroom is spectacular! We found it difficult to leave the cottage and so ate all but one meal right in the kitchen- just too relaxing to go anywhere!Robert is pleasant to deal with and bonus was his allowing us to bring our pup along.
Stayed 4 nights in Jun 2025

10/10 Excellent

Verified traveller

Beautiful Sunrises

Quaint, charming and relaxing, this beach cottage is a tiny slice of heaven.
Stayed 2 nights in May 2019

10/10 Excellent

Kate B.

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

Truly amazing!

The pictures don't do this place justice. It was absolutely breathtaking! We spent a week walking the shoreline, finding sharks teeth, bathing in the sun and enjoying every moment of being on the bay. Thank you, Robert, for sharing this wonderful property!
Stayed 8 nights in Jul 2024

10/10 Excellent

Peggy H., Belgium

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

A real dream

The house has everything one needs. A well equiped kitchen, comfortable beds, a fireplace to warm up the colder evenings and a magnificent deck. We enjoyed the place! Calm and quiet. We woke up with the sound of the waves, had a first cup of coffee on the deck, made a morning walk on the beach and enjoyed the afternoon on the deck and beach. We only left the house to get supplies. Love to go back!!
Stayed 5 nights in Apr 2023

10/10 Excellent

Beth M., Washington, District of Columbia

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

Perfect Covid getaway and great for small children

We had a perfect week away at Always Dreaming! We were looking for a place to get away and do some virtual school/work but also enjoy a secluded beach and this was exactly what we needed. The beach was incredibly private so social distancing was easy and it was so close to the house that we popped out between classes. My favorite part of the beach is hearing the waves and they could be heard from across the house. The owners were friendly and communicative and we were easily able to follow covid distancing guidelines.
Stayed 7 nights in Sep 2020

10/10 Excellent

Erica B.

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

Great stay!

Loved staying here with my husband and two dogs. They loved playing on the beach and it was super private, which was nice. I was impressed by everything that was provided at the house - towels, beach chairs, umbrella, kitchen supplies, even dog waste bags! We loved sitting out back and taking advantage of the lights on the back deck at night. We searched for shells and took a lot of walks. I absolutely loved that the deck had a gate. The dogs loved sunbathing and lounging all day. We'll be back for sure!
Stayed 4 nights in Jun 2019

10/10 Excellent

Saruhan H.

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

Excellent Getaway

This was our third straight year vacationing in this wonderful community. Proximity to DC is remarkable. Within one hour, you are in a completely different environment with the Bay welcoming you for a 180 degree angle view. Private beach, breathtaking views and genuinely nice people that certainly includes the owners. Deb and Robert were great. They invited us to join the 4th of July festivities on the beach, which allowed us to meet other residents of Port Republic. If you are looking for a vacation that provides you with privacy, waterfront with private beach, child-friendly location and a short-drive to Solomon's Island, this is it. Property also provides two decks and there is simply not enough time to take in all the view. We will be back.
Stayed 5 nights in Jul 2019

10/10 Excellent

Jeanette E.

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

Lovely weekend getaway

My best girlfriend & I arrived on a sunny Friday afternoon so immediately got changed into swimsuits to put our feet in the sand and water, then sat on the back porch and watched the waves for hours. Calm, quiet, peaceful. We woke up to rough surf, clouds, and eventually rain on Saturday, but not before a brief walk on the sand and seashell hunting. The house is old, but clean and everything worked. Beds are comfy. Fortunately my friend & I have stayed at VRBOs a number of times so were prepared with our own papertowels, kleenex, and bath soap as none of these were provided. It also would have been helpful to have a book with restaurant recommendations, as the nearest ones are 15-20 minutes away. Would stay here again, but be aware there are no grocery stores or restaurants closeby. Thank you for the perfect weekend to recharge!
Stayed 2 nights in Jul 2024

8/10 Good

John H.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy

Location was key

Location is great, nothing better than walking out back door onto beach. 1st couple days were great with no jellyfish. Played in water, threw out crab baskets & kayak on bay. Then storm came in & jellyfish were significant keeping us to knee deep depths. Decks are nice with upper providing shade to lower with many trek seats. Check in was super easy & house was clean. We are avid shark teeth hunters, & private beach puts Calvert Cliffs to shame especially because they are now closed from walking along them. Huge binoculars were bonus - my sons loved seeing all different ships floating by. Parking was more than sufficient for car plus SUV with trailer. Improvements: listing, there is no hot tub/spa tub (no picture in listing) - there is whirlpool bathtub in master bath, outline states linens included, “About Property” states linens are extra charge. Pet friendly yes, but deck gate has broken board & my dog can fit through, & there was a large wasp nest under & bench/railing on lower deck & my dog got stung. Double bed has 7 degree down slope (apple measure app) towards head. Master bedroom a/c struggles to keep room cooled to 70 when outside temperatures get in 90’s. Dining room only has 2 comfortable seats on loveseat. While WiFi was sufficient, but for some reason provided fire stick lags when moving within apps. PDF from owner are sent through app & cannot be printed for reference & also need to be updated as access to the dock is no longer provided.
Stayed 7 nights in Jul 2024

10/10 Excellent

Dorothy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Every thing was great. We had the harvest moon over the water and beautiful weather for exploring. The beach house is comfortable and lovely.
Stayed 5 nights in Oct 2025

10/10 Excellent

Annette S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic time like always! Thank you Robert again for a pleasant stay! Weather was great, we had a crab feast on the back deck, friends and family came, I love that my dog is able to come and enjoy the water. We all went swimming, found 8 shark teeth and also watched shooting stars from the top deck, It was wonderful to paddle board, we brought our tubes and beach chairs, you can’t get any closer to the beach. This is our second time here and we are planning to make a couple plans for next year. Robert I hope this home will be available for a long time because I don’t want to go anywhere else, it’s like our dream spot! The home has everything you need. And Robert always replies to messages. Thanks Again and see you for 2026!
Stayed 4 nights in Aug 2025

10/10 Excellent

Nina B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The view was amazing The community was amazing. The house was the perfect size. The communication with the owner was on point. Try to check so we can stay for next year and it was already booked for when we wanted it so we were a little bummed out about that, but we can see why it was exactly what we wanted and my dog did not wanna come home. He wanted to stay at the beach, definitely would recommend this place.
Stayed 7 nights in Jul 2025

10/10 Excellent

adam d.

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

Always dreaming is perfect!

Always super relaxing, and extremely quiet!
Stayed 6 nights in Apr 2025

10/10 Excellent

Karen K.

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

Comfortable home right on the Bay

We have stayed at Robert's space for the last three years, and enjoyed a relaxing stay with a beautiful window on the Chesapeake and all its wildlife. The home is right on Kenwood Beach with two porches were you can sit and watch the eagles and osprey go by on their hunts for fish. There is one bedroom overlooking the Bay with a sliding door out to the top porch. The other bedroom is cozy and allows you to wake up to the sound of the birds in the trees behind the neighborhood. The kitchen is well appointed and the location is close to Prince Frederick and lots of eating options. Robert is a welcoming host and is very responsive to any needs you may have.
Stayed 5 nights in May 2025

10/10 Excellent

Andrea K.

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

Beach cottage

The house was clean and cozy. The access to the beach was great and we found lots of little shark teeth. Also not far from restaurants. Nice, quiet neighborhood.
Stayed 2 nights in May 2025

8/10 Good

kimberley t.

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

Cozy and quiet

We found the house cozy, and clean. Upstairs each bedroom has a private bath. The kitchen was clean and well appointed with both pod and regular coffee makers plus toaster oven. Living room was the downfall, only a sofa, no chairs exepect kitchen or this very hard little bench seat. TV has firestick which is adequate for a week out of your life. The best part is out the back door, the deck is wonderful, the beach small and cozy water was great for small children, watching ships, reading books and watching the sun and moon come up is beautiful. There are plenty of restaurants, and grocery stores between house and Prine Frederick to meet your needs. WE ENJOYED OUR TIME, WOULD DO IT AGAIN.
Stayed 4 nights in Aug 2024

About the host

Hosted by Robert

Host profile image
Love the neighborhood and this is our second home and just around the corner to assist our guests.

Why they chose this property

Comfortable, laid back, friendly neighborhood, good for families and couples

What makes this property unique

Close to so many attractions and great for families. Miles of beach to walk, easy living, a view and location that can't be beat by any other house in the area.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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