Entire home

Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Living room opens onto deck; sofa unfolds to full size bed.

Dining area, opens onto deck; table expands for seating for 10!

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms2 bathroomsSleeps 51000 sq ft

Popular amenities

Parking available
Kitchen
Barbecue grill
Pet-friendly
Outdoor space

Explore the area

St Leonard, MD

Matoaka Beach
‪1 min drive‬
Calvert Cliffs State Park
‪19 min drive‬
Cove Point Lighthouse
‪24 min drive‬

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.
Due to the pandemic we have kept 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 parks for hiking and birdwatching.
PLEASE CONTACT ME BEFORE CLICKING "BOOK IT NOW"
Keywords: Vacation Rental Cottage, Beach House, dog

Property manager

Katherine Nelson

Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen

Pet-friendly

Air conditioning

Outdoor space

Parking available

Water view

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House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 11:00 AM

Children

Children allowed: ages 0–17

Parents are responsible for toddler-proofing

Events

No events allowed

Seating for 10 at the dining table. Ask me.

Pets

Pets allowed: dogs (limit 2 total)

Well behaved dogs are welcome. Add $35. per dog.

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

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

We should mention

A car is required for transport to and from this property

About the area

St. Leonard

Located in St. Leonard, this cottage is 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 Battle Creek Cypress Swamp Sanctuary and Calvert Cliffs State Park. R&J's PlayPark and Annmarie Sculpture Garden and Arts Center are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

View more Cottages in St. Leonard

St Leonard, MD

What's nearby

Flag Harbor Marina - 3 min walk - 0.3 km
Matoaka Beach - 1 min drive - 0.7 km
Jefferson Patterson Park and Museum - 16 min drive - 15.4 km
Calvert Cliffs State Park - 19 min drive - 18.5 km
Cove Point Lighthouse - 24 min drive - 23.7 km

Getting around

Ronald Reagan National Airport (DCA) - 73 min drive

Restaurants

‪Adams Taphouse and Grille - ‬11 min drive
‪The Tavern - ‬5 min drive
‪Vera's White Sands Beach Club - ‬17 min drive
‪Gateway Restaurant & Lounge - ‬12 min drive
‪Frying Pan - ‬14 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).

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 within a 15-minute walk of Long Beach, Flag Harbor Marina and Matoaka Beach. Flag Ponds Nature Park is 0.7 mi (1.2 km) away.

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

marie w.

20 Aug, 2025

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

Location, location, location! A wonderful stay at the Harbor cottage. Beautiful view inside the home of the harbor and having a beach, almost to yourself, a mere block away was priceless. Peaceful. Restful. Very comfortable home with most needed provisions. One hour to Washington DC also so can enjoy the city as well. Enjoyed my stay with my husband and two small pups very much.

Stayed 7 nights in Aug 2025

10/10 Excellent

Coleby M.

14 May, 2025

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

10/10 Excellent

Virginia M.

16 Jun, 2025

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

Harbor Cottage is located in a quiet neighborhood within walking distance to a private beach on the Chesapeake Bay. Lovely views of the marina from the deck and inside house. If you like to cook it has a spacious kitchen. The owner was very responsive to questions. We will definitely rent this property again.

Stayed 5 nights in Jun 2025

10/10 Excellent

Steve D.

27 Nov, 2024

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

10/10 Excellent

Steve M.

20 Mar, 2025

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

Calvert Cliff's Refuel

Stayed here for about 3 weeks for a short term work assignment, very clean and pretty well stocked. No issues, I'd stay again.

Stayed 20 nights in Feb 2025

10/10 Excellent

Nick G.

18 Oct, 2024

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

10/10 Excellent

Gloria V.

1 Dec, 2024

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

8/10 Good

David S.

23 Apr, 2025

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

Short but sweet trip.

Our annual trip with our grand kids (5 and 10) on their spring break. We always try to go some place new but within an hour or so from their home near Alexander. This place fit us wonderfully! Kids had a ball! Loved the beach- easy walk! Too cold to swim but they loved the sand. Lots of special yhings to do in the area with a short drive. Kitchen was awesome, well stocked and clean. Not much yard to play in but didn’t need it with beach.

Stayed 5 nights in Apr 2025

10/10 Excellent

Suzi S.

31 Aug, 2024

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

Lovely

I really enjoyed the area and property

Stayed 7 nights in Aug 2024

10/10 Excellent

Ellen R., New Market, Maryland (USA)

31 Aug, 2023

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

10/10 Excellent

AMJ v.

28 Jul, 2024

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

Thank you!

We really enjoyed our stay at this charming cottage. Thank you for hospitality!

Stayed 9 nights in Jul 2024

10/10 Excellent

eileen m.

8 Oct, 2023

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

10/10 Excellent

Jason H.

4 Aug, 2025

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

Great little cottage in a quiet neighborhood with a small marina across the road. Katherine was a great host and messaged us the day of our arrival to let us know of storms in the area and informed us where flashlights were in case of a power outage. Overall the cottage was very clean and homey, it reminded me of my grandmother's place in Baltimore. All basic amenities in the kitchen are provided, if you need a small store to grab a few things from, there is a Dollar General not too far from the cottage. Any larger shopping trips needing a larger grocery store, they are about a 20-30 minute drive. No washer and dryer on site, but the laundromats are about the same distance away. There are some great beaches nearby including the one right by the cottage. We liked the beach at Flag Ponds Nature Park over Calvert Cliffs. Flag Ponds has more traffic, but it is a long beach with plenty of room. Calvert Cliffs is also nice, but there is a long hike (almost 2 miles each way) to get there. The Calvert Marine Museum is also nearby and was a great way to learn some local and rich history. This is also close to the fishing pier that our son was very excited to go to. Washington D.C. is about an hour away, so a day trip is very easy to do. The Steven F. Udvar-Hazy center in VA is a must do.

Stayed 6 nights in Jul 2025

10/10 Excellent

JoAnne M.

22 Oct, 2024

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

Relaxing stay

This is a lovely home that is well equipped for all your needs. The kitchen has everything and there are many beach chairs to use at the beach a short walk away. You will have a parking pass if you would rather not walk.wouldrathernot not walk.

Stayed 5 nights in Oct 2024

10/10 Excellent

Verified traveller

3 May, 2023

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

This review was submitted before 2018 and has not been verified.

10/10 Excellent

susanne f.

22 Dec, 2017

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

10/10 Excellent

Brian N.

31 May, 2023

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

10/10 Excellent

eileen m.

7 May, 2024

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

Always Delightful

Another wonderful stay at Harbor Cottage! The location, the neighborhood and access to the beach and activities can't be beat. The host is very thoughtful and a great communicator.

Stayed 6 nights in Apr 2024

10/10 Excellent

Mark J.

10 Jul, 2023

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

Wonderful place

Very clean, very quiet. Fantastic location. Pretty easy for elderly aunt to navigate deck and beach.

Stayed 7 nights in Jul 2023

10/10 Excellent

jason s.

28 Sept, 2024

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

perfect

been staying at this perfect setting for years. ownership always gracious hosts. couldn't find a rental with better neighbors and accessibility to beach. look forward to next year.

Stayed 14 nights in Sep 2024

10/10 Excellent

susan d.

1 Aug, 2024

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

Beach heaven

This was an amazing trip. The cottage is just perfect. The beach is wonderful. I wouldn’t change a thing. Thank you.

Stayed 21 nights in Jun 2024

10/10 Excellent

eileen m.

24 Dec, 2024

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

Always a Delight

We've had the pleasure of staying at Harbor Cottage multiple times. It's charm and location can't be beat. It is always spotlessly clean and has a cozy beachy feel. In a quiet neighborhood, right across a private lane from picturesque Flag Harbor, it's peaceful and feels out of the way, but is only a few minutes drive to area attractions like Calvert Cliffs and Solomons. The dog friendly community beach is 1/2 block walk (or drive) down the lane. We have spent hours there searching for fossil shark teeth, or just watching the bald eagles and ospreys fly. If you are visiting the area do yourself a favor and stay at Harbor Cottage!

Stayed 4 nights in Dec 2024

10/10 Excellent

Simon R.

29 Aug, 2023

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

Lovely cottage, beautiful location for enjoying the Chesapeake

The house was very clean and comfortable and 2 minutes walk from a private beach. We really enjoyed staying there and strolling along the seashore looking for fossils. Katherine was very easy to communicate with and we'd happily recommend staying at this property, if you're looking for a quiet, relaxing place to stay to explore this beautiful area.

Stayed 4 nights in Aug 2023

10/10 Excellent

Brian S.

16 May, 2024

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

Wonderful place to stay!

Wonderful place for a family get away. The house is perfect to spend time with family… it has a great open layout and a full bathroom for each of the bedrooms. The house is also clean, and the heat and air conditioning worked great. There is a nice view of boats out the front windows, and the beach was a very short walk away. I highly recommend this properly.

Stayed 4 nights in May 2024

10/10 Excellent

Diane L.

30 Jun, 2023

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

Love this place!

2nd time staying here. Great beach - long, uncrowded, & clean w/ soft sand. Quiet neighborhood w/ nice neighbors. Clean & comfortable house. Very dog-friendly.

Stayed 4 nights in Jun 2023

About the host

Hosted by Katherine Nelson

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.