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Cottage on the Bay

St. Leonard accommodation with kitchen

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Photo gallery for Cottage on the Bay

Sun loungers, beach towels
Outdoor dining
Property grounds
Exterior
Fridge, microwave, oven, stovetop

Reviews

8.8 out of 10
Excellent

Entire home

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Saint Leonard, MD
  • Place, Flag Ponds Nature Park
    ‪6 min walk‬
  • Place, Flag Harbor Marina
    ‪8 min walk‬
  • Place, Matoaka Beach
    ‪2 min drive‬

Room options

About the area

St. Leonard

In St. Leonard .Within a 10-minute walk of the cottage, you'll find Chesapeake Bay and Flag Ponds Nature Park. Also, Flag Harbor Marina is within half a mile (1 km) and Northern Chesapeake Bay is within 2 miles (3 km).
View more Cottages in St. LeonardOpens in a new window

What's nearby

  • Flag Ponds Nature Park - 6 min walk - 0.5 km
  • Flag Harbor Marina - 8 min walk - 0.7 km
  • Matoaka Beach - 2 min drive - 1.4 km
  • Calvert Cliffs State Park - 16 min drive - 17.5 km
  • Patuxent River Naval Air Station - 45 min drive - 44.1 km

Restaurants

  • ‪Linda's Produce Stand - ‬11 min drive
  • ‪Vera's White Sands Beach Club - ‬18 min drive
  • ‪Frying Pan - ‬15 min drive
  • ‪Adam's The Place For Ribs - ‬12 min drive
  • ‪The Tavern - ‬6 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Cottage on the Bay

Relax with the whole family at this peaceful place to stay. This beach cottage is in walking distance or a short drive to three private beaches in our community. We provide a parking pass to two of the beaches (one has no parking available).

1 hour from DC/Joint Base Andrews /Annapolis. 45 minutes from Waldorf. 15 minutes from Solomons Island and Prince Frederick

Updated pictures 7/3/2023.

The cottage sits on a hill (there are steps and a grassy hill to access the front or back doors). It has 2 bedrooms with one with queen size bed 43 inch smart TV, and one with bunk beds (twin and full size bed) with a 43 inch smart TV and a spacious bathroom with tub. The living room has a 55 inch smart TV, couch, two chairs, pellet stove. The fully stocked kitchen has spices, cookware, fiesta-ware dishes, dishwasher and offers a 4 chair seating dining table. There is a washer/dryer combo (all in one- it washes and dries in the same machine) available, please note: a wash/dry cycle will take 3-4 hours total. Laundry detergent is not provided. For more space information: click each picture.

Coffee, teas, spices and olive oil are provided.

Shared spaces and items: parking pad (this is a tight fit…two large vehicles will not fit best suited for mid size to compact additional parking can be provided a block away from the property) , fire pit area/back yard, two kayaks and two paddle boards are available for use and are shared with Studio on the Bay guests.

Also, if you need more room we can arrange to combine Studio on the Bay with the Cottage for a discounted rate (if not currently booked/rented).

Please see our other locations: “Studio on the Bay” in Saint Leonard Md or “Cabin in the Woods” in Oakland Md.

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Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 1,845 reviews
The price is CA $160
CA $229 total
includes taxes & fees
May 25 - May 26
Historic Inns of Annapolis

Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Hot tub

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Things to do

  • Kayak
  • Paddleboard

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM

Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you complete the following before checking out:

Load and start the dishwasher

Strip any used beds, gather used towels, and store extra beds

Remove personal items, remove leftover food and drinks, and take out the trash

Turn off the lights, lock the doors, and return the keys

Upon checking out please place all sheets and towels in the hamper and have any dishes washed.

Return HVAC to 76 in summer (AC) and 68 in winter (heat).

Trash receptacle is a BLUE Amber’s can on the left side of the parking pad.

Failure to complete these may result in a negative review from the host.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited.

Frequently asked questions

Does Cottage on the Bay have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Cottage on the Bay to the beach?

This cottage is 0.8 mi (3-min drive) from Long Beach and 1.1 mi (3-min drive) from Matoaka Beach. Don't forget your sunscreen!

Does Cottage on the Bay offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Cottage on the Bay?

No, there is no casino at this cottage.

What time is check-in at Cottage on the Bay?

Check-in begins at 3:00 PM.

Is there free parking at Cottage on the Bay?

Free parking is not available at this cottage.

Does Cottage on the Bay have a pool?

This cottage does not have a pool.

Does Cottage on the Bay have a spa?

There are no spa services available at this cottage.

How close is Cottage on the Bay to downtown St. Leonard?

This cottage is 0.7 mi away from Calvert Beach-Long Beach.

Cottage on the Bay Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 2 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 1 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

8.0/10

Cleanliness

Reviews

10/10 Excellent

Mark T.

Stayed 4 nights in Nov 2025

10/10 Excellent

k w.

Liked: Cleanliness
We had a wonderful visit! The cottage was exceptionally equipped with towels, kitchen, beach chairs, wood for the fire pit, ect.
Stayed 2 nights in Aug 2025

6/10 Okay

Victoria M.

Just know what to expect.

This property has some good qualities. For one, it is right on the water, and you have access to three small beaches and good fishing. It was nice to wake up and drink coffee next to the waves. The house was stocked and seemed to have everything we could’ve needed. However, for us, the negatives far outweighed the positives here. Most significantly to me, the property did not mention that the outdoor amenities - the fire pit, grills, and boats - are shared between you and the adjoining property. The adjoining property is actually a studio garage in the same yard. The fire pit sits directly in front of the other “apartment,” so you will stare directly into the other home should you sit out at night. In fact, this house has little to no privacy at all. If privacy is important to you, you will not enjoy this property - at either sides, you stare directly into the windows (and sometimes the eyes) of neighbors. The house was also grubby. There were dirty dishes in the dishwasher; the knob falls off the shower every time you turn it on. The washer/dryer combo works so inefficiently that it’s not worth your time to use it at all (that is, if you figure out how to use the machine via YouTube, as per the owners’ instructions). Yet, the owners were kind and responsive when I reached out to them upon arrival. They even updated their listings to address some of the aforementioned issues. Just know what to expect at this location, and be willing to relinquish your privacy and perhaps some
Stayed 3 nights in Jul 2023