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Our Always Dreaming Cottage - The Bay At Your Back Steps
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Reviews
9.8 out of 10, Loved by Guests
Top 10% based on
2 bedrooms2+ bathroomsSleeps 41240 sq ft
Popular amenities
Explore the area

Port Republic, MD
- Place, Matoaka Beach7 min drive
- Place, Flag Ponds Nature Park8 min drive
- Place, Battle Creek Cypress Swamp Sanctuary8 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.
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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- Pet-friendly
10.0 out of 10, Exceptional, (21 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 24
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
Events allowed
With prior agreement w/owner
Pets
Pets allowed
Please provide info on pets in order to be approve
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
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 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 hiking and ecotours.

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
- Flag Harbor Marina - 8 min drive - 7.5 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
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.6/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
9.6/10
Listing accuracy
Reviews
Verified
12 Jan, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jan 2026
Verified
10/10 Excellent
adam d.
10 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
adam d.
Stayed 5 nights in Sep 2025
Verified
10/10 Excellent
Dorothy C.
7 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Dorothy C.
Stayed 5 nights in Oct 2025
Verified
10/10 Excellent
Michael C.
13 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Michael C.
Stayed 4 nights in Sep 2025
Verified
10/10 Excellent
Anthony A.
20 Aug, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anthony A.
Stayed 5 nights in Aug 2025
Verified
10/10 Excellent
Kate B.
30 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay

Kate B.
Stayed 8 nights in Jun 2025
Verified
10/10 Excellent
adam d.
28 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Always dreaming is perfect!
adam d.
Stayed 6 nights in Apr 2025
Verified
10/10 Excellent
Daniel S.
4 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stay on the Bay
Daniel S.
Stayed 4 nights in Jun 2025
Verified
10/10 Excellent
Andrea K.
15 May, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beach cottage
Andrea K.
Stayed 2 nights in May 2025
Verified
10/10 Excellent
Donna D.
3 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful cabin
Donna D.
Stayed 4 nights in Oct 2023
Verified
10/10 Excellent
Nina B.
12 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nina B.
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Elizabeth T.
5 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Annual trip
Elizabeth T.
Stayed 4 nights in Jun 2024
Verified
10/10 Excellent
Elizabeth T.
1 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay!
Elizabeth T.
Stayed 5 nights in Jul 2023
Verified
10/10 Excellent
Annette S.
3 Sept, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy

Annette S.
Stayed 4 nights in Aug 2025
Verified
10/10 Excellent
Jason K.
25 Jul, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Bay Cottage. Excellent stay.
Jason K.
Stayed 5 nights in Jul 2020
Verified
10/10 Excellent
Stephanie M.
15 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous Stay!
Stephanie M.
Stayed 4 nights in Apr 2023
Verified
8/10 Good
Diane S.
13 Jul, 2024
Liked: Check-in, communication, location, listing accuracy
Great views.
Diane S.
Stayed 6 nights in Sep 2023
Verified
10/10 Excellent
Kevin K.
13 May, 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Stay at the Beach
Kevin K.
Stayed 5 nights in May 2021
Verified
10/10 Excellent
Amy C.
28 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the location, a bit of everything
Amy C.
Stayed 3 nights in May 2023
Verified
10/10 Excellent
Annette S.
15 Jul, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




Annette S.
Stayed 4 nights in Jul 2025
Verified
10/10 Excellent
adam d.
14 Apr, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet and relaxing!
adam d.
Stayed 4 nights in Apr 2023
Verified
10/10 Excellent
Amanda A.
8 Jun, 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely, Relaxing Getaway
Amanda A.
Stayed 2 nights in Jun 2020
Verified
10/10 Excellent
Aleksandr G.
3 Jun, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect place to get away from the city
Aleksandr G.
Stayed 6 nights in May 2023
Verified
10/10 Excellent
Lisa B.
27 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chesapeake bay
Lisa B.
Stayed 4 nights in May 2024
Verified
10/10 Excellent
Jason K.
26 Jul, 2018
Beautiful property
Jason K.
Stayed 6 nights in Jul 2018
About the host
Hosted by Robert
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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