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Our Always Dreaming Cottage - The Bay At Your Back Steps

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A wooden deck with a railing overlooking the ocean, a covered seating area with chairs, and a wooden structure with a light fixture.
A two-story beachfront house with a wooden deck and stairs leading to a balcony.
A compact living space with a kitchenette, wooden paneling, a floral sofa, and a dining area.
A room with a desk, chair, and a view of the ocean through large windows.
A room with a bed, a dresser, a television, and a view of the ocean through a sliding door.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area
Set along the shore, this cottage accommodates 4 guests with 2 bedrooms and 2 bathrooms. It features beach views and offers outdoor areas including a patio, deck, and balcony. The stay is pet-friendly, and adventure activities such as sailing, fishing, and swimming await nearby. Explore attractions like Matoaka Beach and Flag Ponds Nature Park.

Highlights

  • The great outdoors

    Guests love the outdoor space here.
  • On the beach

    A rare beachfront property in the area - enjoy direct access to the sand and sea.
  • Centrally-located

    You're never far from where you need to be with this convenient location.
2 bedrooms2+ bathroomsSleeps 4

Popular amenities

  • On beach
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Laundry room
  • Air-conditioning

Explore the area

View in a map
Port Republic, MD
  • Place, Matoaka Beach
    ‪8 min drive‬
  • Place, Flag Ponds Nature Park
    ‪10 min drive‬
  • Place, Battle Creek Cypress Swamp Sanctuary
    ‪10 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.



Our prices include all fees. No hidden fees.

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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: family gatherings, birthday parties, weddings

With prior agreement w/owner

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Pets

Pets allowed: limit 1 total

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.

Important information

You need to know

Property # 4523682
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 16
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Port Republic

Located in Port Republic, this cottage is on the beach. The area's natural beauty can be seen at Chesapeake Bay and Battle Creek Cypress Swamp Sanctuary, 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 snorkelling and rafting nearby, or enjoy the great outdoors with ecotours and hiking/biking trails.
Map
Port Republic, MD

What's nearby

  • Matoaka Beach - 8 min drive - 9.0 km
  • Flag Harbor Marina - 9 min drive - 9.6 km
  • Flag Ponds Nature Park - 10 min drive - 10.0 km
  • Battle Creek Cypress Swamp Sanctuary - 10 min drive - 11.4 km
  • Calvert Cliffs State Park - 17 min drive - 18.8 km

Restaurants

  • ‪McDonald's - ‬10 min drive
  • ‪Foster's Grille Prince Frederick - ‬10 min drive
  • ‪First Watch - ‬10 min drive
  • ‪Dunkin' - ‬9 min drive
  • ‪Domino's Pizza - ‬9 min drive

Frequently asked questions

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

Yes, this property allows pets (limit 1 total).

How much does it cost to stay at Our Always Dreaming Cottage - The Bay At Your Back Steps?

As of 19 Sept 2026, prices found for a 1-night stay for 2 adults at Our Always Dreaming Cottage - The Bay At Your Back Steps on 30 Nov 2026 start from £1,218, 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 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

9.6

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. 133 out of 155 reviews
Rating 8 - Good. 16 out of 155 reviews
Rating 6 - Okay. 4 out of 155 reviews
Rating 4 - Poor. 1 out of 155 reviews
Rating 2 - Terrible. 1 out of 155 reviews

9.6/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyed our stay in August. Waters edge location allowed views of Blue Heronand a school of sharks.
Stayed 4 nights in Aug 2026
Response from VrboOwner on 16 Sept 2026
We seem to have more, larger herons this year. Sharks uncommon. Thanks for the nice note.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property and the host were great. You simply can not beat a sand backyard. Very secluded beach experience. Ospreys everywhere hunting for fish, serene waves breaking in the distance, many crabs easily seen. The kids found 22 shark teeth!
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was great! Can't beat the location and the house has everything you need. My wife, son and I we're very comfortable for a week, and we would definitely consider staying here again (we almost NEVER stay in the sabe place twice). Owner was responsive and helpful, no concerns at all. Highly recommend for a quiet, peaceful vacation spot.
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was as showed peaceful and great for dog owners never barely anyone on beach
Stayed 8 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Waterfront location is perfect. Very close to other sights and services. Easy to get to.
Stayed 4 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful location! What a relaxing stay!
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
As advertised everything was great, relaxing and cozy!
Stayed 5 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location, very clean, though it is probably time for some updated pictures/info. Large amount of overgrown vegetation around deck, sliders and closet door need attention. There is no key available for the pier as advertised, this wasn't a big deal to us but instructions should be updated with more current info for those that might want that. We appreciated the info about places to go and warning of the jellyfish, we saw a lot but avoided stings. Very quiet, peaceful place, we didn't cook but it looked like a pretty well stocked kitchen. Couches not comfortable even to sit in, again maybe time for updating. Check in instructions very clear and helpful. Nice, quiet getaway for us. Highlights: watching the heron and looking for shark teeth and sea glass. Found seamless, but no shark teeth, watching cowbell rays feed each day, visiting local lighthouses, though Cove Point is now being renovated with scaffolding, so check website and call before you go, Sculpture gardens were nice, and Calvert Marine Museum was great. Great places to eat all around the area.
Stayed 6 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location
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!
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Wonderful cabin

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 6 Oct 2020
Hi Jason - Thank you for the compliments, we hope to see you again!
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 11 Jun 2021
Thanks Kevin! Appreciate your suggestions too, welcoming you all back this summer.
Verified review

10/10 Excellent

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

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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