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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

A kitchen with a wooden countertop, two black chairs, a stainless steel sink, and hanging pots.
A circular pond surrounded by a brick border, with green lily pads and some leaves floating on the water.
A spacious living room with a white sofa, a coffee table, and a white armchair. There is a ceiling fan, a window with curtains, and a door leading outside.
A spacious living room with a sofa, a coffee table, and a TV. There is a dining table with chairs and a window with plants.
A kitchen with a window, wooden cabinets, and a dining area with a chair and table.

Reviews

10 out of 10
Exceptional

Highlights

  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Discover nearby landmarks
    Walk to Chesapeake Bay
4 bedrooms2 bathroomsSleeps 7

Popular amenities

  • Patio
  • Dog-friendly
  • Toys
  • On-site fitness centre
  • Barbecue
  • Air-conditioning

Explore the area

View map
Annapolis, MD
  • Place, Northern Chesapeake Bay
    ‪2 min walk‬
  • Place, Bay Ridge Beach
    ‪6 min walk‬
  • Place, U.S. Naval Academy
    ‪15 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪49 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
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
We love dogs, love to keep them off the furniture
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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

Property # 20241723
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
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

Bay Ridge, a neighbourhood in 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.
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Map
Annapolis, MD

What's nearby

  • Northern Chesapeake Bay - 2 min walk - 0.2 km
  • Bay Ridge Beach - 6 min walk - 0.6 km
  • U.S. Naval Academy - 15 min drive - 8.3 km
  • Annapolis City Dock - 16 min drive - 9.0 km
  • Chesapeake Bay Bridge - 31 min drive - 24.9 km

Getting around

  • Odenton Station - 28 min drive
  • Fort Meade, MD (FME-Tipton) - 37 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪The Beacon Restaurant - ‬9 min drive
  • ‪Boatyard Bar & Grill - ‬10 min drive
  • ‪Royal Farms - ‬9 min drive
  • ‪Grump's Cafe - ‬6 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 6 Oct 2026, prices found for a 1-night stay for 2 adults at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting on 4 Feb 2027 start from AU$2,031, 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?

Located in Bay Ridge, 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).

Reviews

10

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. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

9.6/10

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
Cute cottage conveniently located near our daughter’s wedding venue. It was clean & comfortable with a nice backyard in a beautiful neighborhood.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great pet-friendly cottage in the Bay Ridge community, one of the originals with modern updates. The host was very responsive and accommodating. The fenced back yard has great little nooks and koi ponds with a bamboo border that makes it very private. We would definitely rent again!
Stayed 7 nights in Aug 2026
Response from VrboOwner on 1 Sept 2026
Thanks so much, Mary Beth! It was a pleasure to host you and we'd love to have you back to stay anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The pictures don’t do this house justice. It’s more spacious than it looks, tastefully decorated, and has all the necessary. This is the house that’s been lived in so it has a real personality, nice art, a quiet backyard. It’s extremely well situated, close to many beaches, and the neighborhood is quaint and walkable. Heather was fantastic. She always responded quickly and addressed our needs. We will definitely come back.
Stayed 3 nights in Jul 2026
Response from VrboOwner on 17 July 2026
Thanks so much for your thoughtful review! I am so glad you had a good stay. Please do book again when you come to Annapolis. It was a pleasure to host your family.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a beautiful house with so much fun character! Our host, Heather was very communicative and the setting was amazing! The only slight downside was that the upstairs was very hot, making sleeping slightly sticky. Overall, wonderful place within a beautiful community.
Stayed 4 nights in Jun 2026
Response from VrboOwner on 2 July 2026
Thank you, Miriam, I'm so glad you enjoyed your stay! It was a pleasure hosting you. We find that setting the two HVAC systems much cooler at night keeps things comfortable, and the extra fans help. I hope guests will reach out with questions about how to optimise settings.

About the host

Hosted by Heather Macintosh

Host profile image

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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