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Our Always Dreaming Cottage - The Bay At Your Back Steps

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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, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2+ bathroomsSleeps 41240 sq ft

Popular amenities

  • Kitchen
  • Air conditioning
  • Laundry
  • Outdoor Space

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.



Our prices include all fees. No hidden fees.

Add dates for prices

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 complete the following before checking out:
Strip any used beds and gather used towels
Remove personal items and take out the trash
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 there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the neighborhood

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 Calvert Marine Museum are cultural highlights. R&J's PlayPark and Kocen Arts Center are also worth visiting. Discover the area's water adventures with snorkeling 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
  • Biscoe Gray Farm - 8 min drive - 10.8 km
  • Calvert Cliffs State Park - 12 min drive - 16.7 km

Restaurants

  • ‪Foster's Grille Prince Frederick - ‬10 min drive
  • ‪McDonald's - ‬10 min drive
  • ‪Dunkin' - ‬9 min drive
  • ‪Linda's Produce Stand - ‬4 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 does it cost to stay at Our Always Dreaming Cottage - The Bay At Your Back Steps?

As of Apr 5, 2026, prices found for a 1-night stay for 2 adults at Our Always Dreaming Cottage - The Bay At Your Back Steps on Apr 14, 2026 start from $309, 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?

Onsite 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?

Check-out 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 from Chesapeake Bay and Northern Chesapeake Bay. Matoaka Beach and Long Beach are also within 6 mi (10 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 122 out of 139 reviews
Rating 8 - Good. 14 out of 139 reviews
Rating 6 - Okay. 1 out of 139 reviews
Rating 4 - Poor. 1 out of 139 reviews
Rating 2 - Terrible. 1 out of 139 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified

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
Verified

10/10 Excellent

Lisa B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our week at the cottage was wonderful. The home is right on the beach and the views (especially the sunrises) were spectacular! We enjoyed frequent walks on the beach looking for shells and fossils. The location was convenient to restaurants and shops, but also in a quiet and friendly neighborhood. The home was comfortable, just the right size for us, and it being pet friendly was a huge plus. The kitchen had everything we needed, giving us the option of easily preparing meals there when preferred. Robert was a great host, extremely responsive, and very helpful! We would rent it again in a heartbeat! Thanks so much for having us, it was just the escape we needed!
Stayed 7 nights in Jan 2026
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Donna D.

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

Wonderful cabin

Great property and location- plan to return!
Stayed 4 nights in Oct 2023
Verified

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
Verified

10/10 Excellent

Elizabeth T.

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

Annual trip

As always, we had a great time at Roberts property! Thanks for a wonderful stay we will be back soon!
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Elizabeth T.

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

Wonderful stay!

We had a great stay- perfect space for our family of 4! The beds were VERY comfortable and ensured we had a wonderful night sleep. We will definitely be back!
Stayed 5 nights in Jul 2023
Verified

10/10 Excellent

Jason K.

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

Beautiful Bay Cottage. Excellent stay.

Beautiful cottage with great views. Beach acces was amazing, and the owners are a pleasure to deal with.
Stayed 5 nights in Jul 2020
Verified

10/10 Excellent

Stephanie M.

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

Fabulous Stay!

We loved our stay at Always Dreaming Cottage. It was truely amazing to be right on the water. We can't wait for a return trip!
Stayed 4 nights in Apr 2023
Verified

8/10 Good

Diane S.

Liked: Check-in, communication, location, listing accuracy

Great views.

Beautiful location. Needs some updating and better furniture.
Stayed 6 nights in Sep 2023
Verified

10/10 Excellent

Kevin K.

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

Great Stay at the Beach

Wonderful beachfront vacation. Loved hanging at the beach with the family and sitting on the porch. Lots of activities nearby.
Stayed 5 nights in May 2021
Verified

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
Verified

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
Verified

10/10 Excellent

adam d.

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

Quiet and relaxing!

This place is in a perfect location for fossil hunting! Very quiet and extremely relaxing!
Stayed 4 nights in Apr 2023
Verified

10/10 Excellent

Amanda A.

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

Lovely, Relaxing Getaway

We are so lucky to have found this place! All the amenities and right on the beach. Our kids played for hours!
Stayed 2 nights in Jun 2020
Verified

10/10 Excellent

Aleksandr G.

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

Perfect place to get away from the city

Good place for relaxing vacation. Walk on the beach, in the nearby parks. Boardwalk is just a short drive away.
Stayed 6 nights in May 2023
Verified

10/10 Excellent

Lisa B.

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

Chesapeake bay

We had such an amazing long weekend. We loved fossil hunting and walking on the beach. What a relaxing break.
Stayed 4 nights in May 2024
Verified

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
Verified

10/10 Excellent

Jason K.

Beautiful property

Our family had a wonderful time collecting sharks' teeth and shells. Beautiful house and great surrounding area.
Stayed 6 nights in Jul 2018

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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