Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach

Saint Leonard, Maryland
$191 avg/night
Minimum Stay 4 Nights
Bed 2

Bed

Bath 2

Bath

Home Cottage

Property Type

Sleep 5

Max Sleeps

Night 4 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    2 Total Pets Pet Friendly Service Animals Exempt From Fees Welcoming Dogs Only
  • BEACH

    Beach Sun Loungers
  • SAFETY

    Deadbolt Lock Fire Extinguisher First Aid Kit No Carbon Monoxide Detector (host Has Indicated There Is No Carbon Monoxide Detector Or Gas Appliances On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms
  • GENERAL

    Double-glazed Windows Recycling Unit Size: 1000 Sq Ft (93 Sq M) Uses Some LED Lighting Water-efficient Showers Only Water-efficient Toilets Only
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Lobster/crab Pot Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Near Laundromat
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Barbecue Grill Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Golfing On Site Kayak On Site Kayaking Nearby Marina Nearby Power Boating Nearby Swimming Nearby Water Park Nearby Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Books DVD Player Games Stereo Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware
  • LOCATION HIGHLIGHTS

    Near A Hospital On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    No Elevators Smoke-free Property

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Availability

Review Review

  • M B.

    Submitted Apr 9, 2026

    Stayed Apr 1, 2026

    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!

  • Judith B.

    Submitted Jan 5, 2026

    Stayed Dec 13, 2025

    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.

  • Ed O.

    Submitted Dec 1, 2025

    Stayed Nov 4, 2025

    Host was easy to communicate with. The place is wonderful!

  • jason s.

    Submitted Oct 19, 2025

    Stayed Sep 19, 2025

    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.

  • eileen m.

    Submitted Oct 13, 2025

    Stayed Oct 7, 2025

    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.

  • Jeannine C.

    Submitted Sep 20, 2025

    Stayed Sep 3, 2025

    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.

  • edith f.

    Submitted Sep 18, 2025

    Stayed Sep 11, 2025

    Everything was just as listed. Beautiful house and neighborhood.

  • Judy O.

    Submitted Aug 26, 2025

    Stayed Aug 22, 2025

    Wonderful location w easy access to beach for fishing and shelling ! Cottage very clean and comfortable w a new kitchen , large dining table and big deck ! Stores and restaurants not far but beware they are closed on Mondays except fast food ! Very welcoming community A-big thank you to the owner the O’s

  • Pamela B.

    Submitted Aug 24, 2025

    Stayed Aug 17, 2025

    The cottage was everything as advertised and more!! We loved it so much that we could live there forever!!Katherine was awesome!!!

  • marie w.

    Submitted Aug 20, 2025

    Stayed Aug 9, 2025

    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.

  • Jason H.

    Submitted Aug 4, 2025

    Stayed Jul 27, 2025

    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.

  • Virginia M.

    Submitted Jun 16, 2025

    Stayed Jun 11, 2025

    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.

  • Coleby M.

    Submitted May 14, 2025

    Stayed May 10, 2025

    Cozy spot on bay. Great for beach hikes and birdwatching.

  • David S.

    Submitted Apr 23, 2025

    Stayed Apr 13, 2025

    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.

  • Steve M.

    Submitted Mar 20, 2025

    Stayed Feb 17, 2025

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

  • eileen m.

    Submitted Dec 24, 2024

    Stayed Dec 15, 2024

    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!

  • Gloria V.

    Submitted Dec 1, 2024

    Stayed Nov 26, 2024

    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.

  • Steve D.

    Submitted Nov 27, 2024

    Stayed Oct 30, 2024

    I will be back next year this location was great.

  • JoAnne M.

    Submitted Oct 22, 2024

    Stayed Oct 17, 2024

    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.

  • Nick G.

    Submitted Oct 18, 2024

    Stayed Oct 8, 2024

    My mother loved the harbor and beach that was right there.

  • Cathy H.

    Submitted Oct 4, 2024

    Stayed Sep 30, 2024

    This is our third year staying at this serene and peaceful property. Although the weather was dismal it did not deter us from enjoying a recharging and tranquil week. We will definitely be back next year and many more years to follow. Thanks for the memories!

  • jason s.

    Submitted Sep 28, 2024

    Stayed Sep 14, 2024

    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.

  • Suzi S.

    Submitted Aug 31, 2024

    Stayed Aug 24, 2024

    I really enjoyed the area and property

  • susan d.

    Submitted Aug 1, 2024

    Stayed Jun 26, 2024

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

  • AMJ v.

    Submitted Jul 28, 2024

    Stayed Jul 18, 2024

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

Your dates are Available!

Total

Includes taxes and fees
$245+
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