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Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

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A balcony with a glass table and chairs, overlooking a marina with boats and a river.
A brick house with a front porch, surrounded by lush greenery and flowering plants.
An outdoor seating area with a glass-top table, chairs, and a view of a marina with boats.
A brick house with a covered porch and a visible number '1570' on the front.
A beach with a calm sea, a sandy shore, and a distant sunset over a hilly landscape.

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Top rated beach location
    Discover paradise at this top rated beach location.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Chesapeake Bay
2 bedrooms2 bathroomsSleeps 5

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Refrigerator
  • Onsite parking available

Explore the area

View in a map
St Leonard, MD
  • Place, Flag Harbor Marina
    ‪3 min walk‬
  • Place, Northern Chesapeake Bay
    ‪9 min walk‬
  • Place, Matoaka Beach
    ‪15 min walk‬

Rooms & beds

2 bedrooms (sleeps 5)

Convertible bed(s)

1 Double Futon

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Harbor Cottage. Relax on the deck overlooking the fishing and sailboats of Flag Harbor opening onto the Chesapeake Bay. Only a three minute walk to the big sand beach famous for fossils from the Miocene period. Very quiet and not crowded. Great fishing from the beach or charter a boat. Shallow water makes for great swimming for kids. Bring your well behaved dog to enjoy the beach and swimming with you.
We keep a vacant day between renters as a courtesy to our cleaners and our arriving guests. These dates are blocked on our calendar.

Washington DC or Annapolis is only one hour away, and the entire Chesapeake Bay area is steeped in American history. Just 15 minutes from the shops and restaurants of Solomons Island, and the terrific Marine Museum there. Many state and county parks for hiking. fossil hunting, and birdwatching.
PLEASE CONTACT ME BEFORE CLICKING "BOOK IT NOW"
Keywords: Vacation Rental Cottage, Beach House, dog

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Parents are responsible for toddler-proofing
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Events

No events allowed
Seating for 10 at the dining table. Ask me.
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Pets

Pets allowed: dogs (limit 2 total)
Well behaved dogs are welcome. Add $35. per dog.
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to complete the following before checking out:
Turn off the lights, lock the doors and return the keys
Please leave the cottage as tidy as you found it. Put trash in outside barrels, leave the beach pass in the kitchen, put the key back in the lock box - and thank you very, very much!
Failure to complete these may result in a negative review from the host.
Well behaved dogs only - please pad the floor under the crate to protect the hardwood floor. Contact me if your dog as ever bitten man or beast.
Our beach is unguarded - swim, fish, and boat at your own risk. Clean-up after yourself and your dog on the beach and neighborhood. No fireworks.
Stay off the cliffs - they are a landslide danger and private property. Fossil hunt at the water line or in the surf for better results and safety.

Important information

You need to know

Property # 60379vb
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
On-site parties or group events are strictly prohibited
Note from host: Seating for 10 at the dining table. Ask me.
Long-term renters welcome
Host has indicated that there are no carbon monoxide detectors or gas appliances on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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

St. Leonard

Located in St. Leonard, this cottage is near a water park and on the waterfront. Flag Harbor Marina and Perigeaux Vineyards and Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Battle Creek Cypress Swamp Sanctuary. R&J's PlayPark and Kocen Arts Center are also worth visiting. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking nearby.
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Map
St Leonard, MD

What's nearby

  • Flag Harbor Marina - 3 min walk - 0.3 km
  • Northern Chesapeake Bay - 9 min walk - 0.8 km
  • Flag Ponds Nature Park - 12 min walk - 1.1 km
  • Matoaka Beach - 15 min walk - 1.3 km
  • Maryland International Raceway - 53 min drive - 62.4 km

Getting around

  • Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

  • ‪Linda's Produce Stand - ‬9 min drive
  • ‪Frying Pan - ‬14 min drive
  • ‪Gateway Restaurant & Lounge - ‬12 min drive
  • ‪The Tavern - ‬5 min drive
  • ‪Patuxent Seafood Company - ‬17 min drive

Frequently asked questions

Is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

On-site parking is available at the property.

What time is check-in at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Check-in begins at 3:00 PM.

What time is check-out at Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach?

Checkout is at 11:00 AM.

Where is Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach located?

Situated on the waterfront, this cottage is steps away from Chesapeake Bay and Flag Harbor Marina. Long Beach and Northern Chesapeake Bay are also within 15 minutes.

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 window
Rating 10 - Excellent. 149 out of 174 reviews
Rating 8 - Good. 23 out of 174 reviews
Rating 6 - Okay. 1 out of 174 reviews
Rating 4 - Poor. 1 out of 174 reviews
Rating 2 - Terrible. 0 out of 174 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family had a great stay at this cottage. Cottage was very clean and was well equipped for our stay. Centrally located to all the amenities in the area and we highly recommend. Host was very organized and communicated quickly when needed. We will be staying here in the future. Can’t wait to return.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Katherine was a pleasure to deal with. Communicating with her was easy and she responded very quickly. The house was as described and everything was neat, clean and organized. It was relaxing to sit on the deck and watch the boats coming and going across the street at the Marina. The beach was really nice and we went down and BBQed there. It is an easy walk, but we took the car to make it easier with all our stuff.I highly recommend checking this home out.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent!
Stayed 4 nights in May 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Enjoyable stay, very quiet area, house was nice; water filters on kitchen sink and refrigerator would be nice. Tubs not elderly friendly and beds could be upgraded. Overall we really like the place.
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
My wife and me rented this cottage to be closer to our family while in the area. We were expecting busy days so we were looking for peaceful nights and that's exactly what we were given. I grew up in Owings and have family scattered throughout Southern Maryland so the location was perfect for visiting in the area plus making a couple of visits to Washington DC while we were in the area. My wife and I enjoyed coming back each night to the clanking of the sail boat rigging that came with the excellent view of the marina. We are definitely planning on returning to this quiet getaway on our next trip to Maryland.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was easy to communicate with. The place is wonderful!
Stayed 21 nights in Nov 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great hosts and great property. The location is nearly perfect. We might have been the first guests of the season or at least when bookings are light, so there were some bumps, but things happen and the hosts made sure everything was handled as best as possible. This might our new "spring break" place! We need to practice our fossil hunting skills because we are terrible!
Stayed 4 nights in Apr 2026
Response from VrboOwner on 15 Apr, 2026
I’m glad we were able to solve your problems quickly and not interfere with your vacation.
Verified review

10/10 Excellent

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

Amazing property we loved it

I will be back next year this location was great.
Stayed 5 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was great! The cottage was well appointed. The hosts were very welcoming, and the all the people we met on our walks were very friendly. I would definitely recommend this cottage.
Stayed 20 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay at Harbor Cottage. We stay there at least once a year and look forward to it every time. Can't beat the location, neighborhood or convenience to the private beach. The cottage is charming with a great view of Flag Harbor right across the street.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

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

Great location

My mother loved the harbor and beach that was right there.
Stayed 7 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was everything as advertised and more!! We loved it so much that we could live there forever!!Katherine was awesome!!!
Our pup Winnie exhausted from exploring all day in her bed for the night.
My husband Bob enjoying the bay with Winnie.
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

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

Quiet Chesapeake Getaway

Cozy spot on bay. Great for beach hikes and birdwatching.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

Lovely Home Near the Beach

House had everything we could have asked for, well stocked kitchen and lots of great information on local attractions available! Very nice location, great value!
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
stay was excellent as always. great Neiborhood to enjoy beach with family and dogs. host was a pleasure to deal with. look forward to another season.
Stayed 15 nights in Sep 2025
Verified review

10/10 Excellent

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

Great Family Get-Away

This was our 3rd summer visit to this home. We love it and will visit again!
Stayed 6 nights in Aug 2023
Verified review

10/10 Excellent

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

Perfect beachside retreat

This house was the perfect fit for our stay in st Leonard. The kitchen was well appointed and the facility was very comfortable. We would definitely stay here again.
Stayed 4 nights in Nov 2024
Verified review

10/10 Excellent

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

Love Staying at Harbor Cottage

Another great stay. The location and charm of Harbor Cottage can't be beat if you are going to the Calvert Cliffs area! Katherine is a wonderful host.
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We Our stay was perfect. The cottage was spotless and had everything we needed.The beach was a minute away and the view off the porch was great. We like to birdwatch and it was fantastic in the marina. We will definitely return.
Stayed 7 nights in Sep 2025
Verified review

10/10 Excellent

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

Another Wonderful Stay at Harbor Cottage!

Had a great time. Many thanks to our hosts.
Stayed 4 nights in Apr 2023
Archival

10/10 Excellent

Perfect cozy cottage!!! We loved our stay!

Everything about our experience was perfect- from the reservation to check out. Katherine was very hospitable! The cottage was perfect for our family gathering- clean and comfy beds were also a plus 👍🏻Can’t wait until our next visit!!
Stayed 4 nights in Dec 2017
Verified review

10/10 Excellent

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

Great little cottage!

We had a wonderful stay at harbor cottage! It was very clean and comfortable. The area is fantastic if you’re looking for someplace to chill and relax. Very dog friendly!
Stayed 4 nights in Apr 2023
Verified review

10/10 Excellent

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

Return trip, great location and property.

This is our second stay, and had a great time on the beach! The house is fully equipped with everything you need and is comfortable. We had a great time and will be back next year!
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

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

Lovely

We really enjoyed our stay!the home had everything we needed! Such a memorable stay, Thank you 😊
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was just as listed. Beautiful house and neighborhood.
Stayed 4 nights in Sep 2025

About the host

Hosted by Katherine Nelson

Host profile image
We love this area for a quick get-a-way: our neighbors are friendly and helpful, and the beach is peaceful and beautiful! We enjoy watching the eagles and ospreys fish, and the large schools of fish that can be seen in the (usually) clear water.

Why they chose this property

We found this peaceful and friendly spot by chance - it's so close to the Washington DC area. The community is very dog-friendly, and when we are alone on the beach, they can romp in the waves off the leash. There aren't dangerous tides, and seldom rough water.

What makes this property unique

We have discovered the fun of fossil hunting, or just sitting at the beach and reading and re-charging our energies. The light, wind, and water are constantly changing. You can walk the beach for hours.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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