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Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting
Photo gallery for Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting
Reviews
1010 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 7185.8 sq m
Popular amenities
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
- Free Wi-Fi
- Air-conditioning
Explore the area
Annapolis, MD
- Bay Ridge BeachPlace, Bay Ridge Beach6 min walk
- U.S. Naval AcademyPlace, U.S. Naval Academy12 min drive
- Annapolis City DockPlace, Annapolis City Dock12 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)40 min drive
Rooms & beds
4 bedrooms (sleeps 7)
Bedroom 1
1 King Bed
Bedroom 2
1 Queen Bed
Bedroom 3
1 Single Bed
Bedroom 4
1 Single Bed
2 bathrooms
Bathroom 1
Soap · Towels provided · Bathtub or shower · Bathtub · Bidet · Toilet · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
Separate dining area
Garden
Dining area
About this property
Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting
Settle in by a cozy wood fire, walk the beaches at sunrise, visit Historic Annapolis museums, restaurants, and vibrant nightlife. The house sleeps 6 or 7 and is fully set up with fresh linens, fluffy towels, a soaker tub, and filled with good books and original art. The private backyard is fully fenced, surrounded by bamboo, two fish ponds and a life-size Buddha statue. Grill something delicious and eat on the back deck, enjoy the birdsong and the fragrant wisteria arbor. It's one of the original 1940s cottages built in the Bay Ridge resort community, renovated for comfort while keeping the charm.
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
We love dogs, love to keep them off the furniture
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Remove personal items and remove leftover food and drinks
Lock the doors and return the keys
Rinse and empty coffee maker
Please leave nothing on wood counter
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
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
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, 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
Annapolis
Annapolis is home to this holiday home. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and some of the area's activities can be experienced at Annapolis Golf Club and Annapolis Landing Marina. Looking to enjoy an event or a game while in town? See what's happening at Tose Family Tennis Center or Alumni Hall.
Annapolis, MD
What's nearby
- Bay Ridge Beach - 6 min walk - 0.6 km
- U.S. Naval Academy - 12 min drive - 7.9 km
- Annapolis City Dock - 12 min drive - 7.9 km
- Westfield Annapolis Mall - 16 min drive - 12.1 km
- Chesapeake Bay Bridge - 24 min drive - 23.1 km
Getting around
- Odenton Station - 28 min drive
- Fort Meade, MD (FME-Tipton) - 37 min drive
Restaurants
- McDonald's - 6 min drive
- Carrol's Creek Cafe - 10 min drive
- Sammy's Italian Pizza Kitchen - 8 min drive
- Boatyard Bar & Grill - 10 min drive
- Royal Farms - 9 min drive
Frequently asked questions
Is Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting pet-friendly?
Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.
How much does it cost to stay at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting?
As of 8 April 2026, prices found for a 1-night stay for 2 adults at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting on 1 June 2026 start from NZ$514, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting?
On-site parking is available at the property.
What time is check-in at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting?
Check-in begins at 4:00 PM.
What time is check-out at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting?
Checkout is at 11:00 AM.
Where is Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting located?
Situated in Annapolis, this holiday home is within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Bay Ridge Beach and Bay Bridge Market Place Shopping Center are also within 3 miles (5 km).
About the host
Hosted by Heather Macintosh
Why they chose this property
Step out the front door and turn right. In two minutes you have the whole length of the wide Chesapeake Bay where you can watch sailboats, osprey, cotton candy clouds, and the best sunrises around. All of it mirrored in the water. Each of our beaches has a different view, and just the right spot to sit and soak it all in.
What makes this property unique
This 1940s cottage has the charm of a favorite summer place, the comfort of a cozy winter getaway, and one of a kind quirky garden. It was called Owl Park when it was built after the Bay Ridge resort made way for summer homes. Now it's a sought-after neighborhood for Annapolitans who enjoy friendly walks, happy dogs, and the woods, beaches and gorgeous views
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