Title: Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=6034082&destination=Annapolis%2C+Maryland%2C+United+States+of+America&selected=125095572&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # 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 ![Sun loungers - Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting (Annapolis)](https://images.trvl-media.com/lodging/126000000/125100000/125095600/125095572/c494f81a.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting (Annapolis)](https://images.trvl-media.com/lodging/126000000/125100000/125095600/125095572/f750bd2f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior detail - Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting (Annapolis)](https://images.trvl-media.com/lodging/126000000/125100000/125095600/125095572/96697fff.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, books, stereo - Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting (Annapolis)](https://images.trvl-media.com/lodging/126000000/125100000/125095600/125095572/11a394f9.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Dining - Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting (Annapolis)](https://images.trvl-media.com/lodging/126000000/125100000/125095600/125095572/ce456712.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies A firepit, a garden, and laundry facilities are just a few of the amenities provided at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting. Stay connected with free in-room WiFi, with speed of 500+ Mbps (good for 6+ people or 10+ devices), and guests can find other amenities such as a gym. ## Reviews 10 Exceptional ### Entire home 4 bedrooms2 bathrooms2000 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Pet friendly - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### 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. ## Property amenities ### Beach - Beach loungers ### Internet - Available in the house: Free WiFi ### Parking and transportation - Wheelchair-accessible parking and van parking available ### Kitchen - Blender - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Lobster/crab pot - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Bidet - Hair dryer - Shampoo - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Separate dining area - Wood stove ### Entertainment - Books - Smart TV - Stereo ### Outdoor areas - Barbecue grill - Firepit - Garden - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - Welcoming dogs only - 2 pets total (up to 50 lbs per pet) ### Suitability/Accessibility - If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking. - 1 accessible parking space - Upper floors accessible by stairs only - Wheelchair-accessible parking - Wheelchair-accessible path of travel - Wheelchair-accessible van parking - Smoking not allowed ### Services and conveniences - Housekeeping (on request) - Iron/ironing board ### Things to do - Gym ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - First aid kit - Fire extinguisher - Deadbolt lock ### General - At least 10% of profits reinvested in community and sustainability - At least 80% lighting from LEDs - Composting - Comprehensive recycling policy - Double-glazed windows - Eco-friendly cleaning products used - Eco-friendly toiletries - Garden - Housekeeping (on request) - Local artist showcase - Local culture and ecosystem education - Locally-owned and organized tours and activities - Unit size: 2,000 square feet - Water-efficient showers - Water-efficient toilets ## Similar properties ![House, 4 Bedrooms | Living area](https://images.trvl-media.com/lodging/116000000/115460000/115456000/115455947/460b766b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Peaceful Pet Friendly Chesapeake Escape 4 Bedroom Home Prince Frederick - Washer - Dryer - Pet friendly - Free WiFi [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&selected=115455947&PinnedHotelID=115455947&HadPinnedHotel=true®ionId=-1&adults=2) ![Oven, stovetop](https://images.trvl-media.com/lodging/121000000/120860000/120855800/120855751/009658d6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 40' Bristol sailboat with spectacular views Stevensville - Kitchen - Parking available - Water view CA $411 CA $595 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-20&endDate=2026-03-21&selected=120855751&PinnedHotelID=120855751&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/98000000/97710000/97708200/97708157/4a4248ac.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Sunny and spacious water view/access home in Annapolis. Arundel on the Bay - Washer - Dryer - Pet friendly - Air conditioning 2.0 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&selected=97708157&PinnedHotelID=97708157&HadPinnedHotel=true®ionId=-1&adults=2) ![TV, offices](https://images.trvl-media.com/lodging/106000000/105550000/105549100/105549011/b24c0f35.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Wright's Cottage- Pet's Welcome & EV Charging Annapolis - Kitchen - Washer - Dryer - Pet friendly 9.2 Wonderful 16 reviews CA $241 CA $508 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24&selected=105549011&PinnedHotelID=105549011&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/112000000/111250000/111246400/111246308/e7831933.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pet Friendly-newly built house in peaceful beach community, located in Riva MD. Riva - Kitchen - Washer - Dryer - Pet friendly [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&selected=111246308&PinnedHotelID=111246308&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101900000/101897400/101897342/dc0187f5.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Neptune by the Water - Pet Friendly Fenced Yard Cape Saint Claire - Kitchen - Washer - Dryer - Pet friendly 9.8 Exceptional 11 reviews CA $263 CA $838 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-24&endDate=2026-03-25&selected=101897342&PinnedHotelID=101897342&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-04-02&endDate=2026-04-03&selected=125095572&PinnedHotelID=125095572&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=125095572,115455947,120855751,97708157,105549011) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 25 ### Check-out Check-out before 11:00 AM Contactless check-out available ### 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: 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. ### Pets Pets allowed Service animals are welcome, and are exempt from fees Welcoming dogs only 2 total (up to 50 lbs per pet) Note from host: We love dogs, love to keep them off the furniture ### 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 This property uses eco-friendly cleaning products Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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 ### We should mention This property does not have elevators ## About the area Annapolis is home to this vacation 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. [Visit our Annapolis travel guide](https://www.expedia.ca/Annapolis.dx6034082) [View more Vacation homes in Annapolis](https://www.expedia.ca/Annapolis-Private-Vacation-Homes.d6034082-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=38.94168,-76.45708&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:qtulFv_tqM%3FS%3FS%3FU%3FS%40S%40S%40S%40Q%40U%40SBS%40SBQBSBSBSBQBSDSDQBQDSDQDQFQDSDQFQFODSHOFOFQFQHOFOHOHOHOFOJOHMHOHMJMJMHMJMJMJKJMJKJKLKJKLIJKLIJILKLILILGLILGLGLGNGLGLGLENENELENELCNCLENCNCNALCNANANANAL%3FNAN%3FNAN%40N%3FN%40L%3FN%40N%40N%40N%40LBN%40NBLBNDNBLBNDNDLDLDNDLFLFLFNFLFLFLHLFLHLHLJJHLHJJLHJJJJLJJJJLJJJLJLHLJLHLJLHNHLHNHNHNHNFNHPHLFPFPFNFNFRFNFPDPDRFPDPDPDRBPDPDRBRBPBRBRBRBR%40P%40RBT%40R%40P%40R%40R%40R%3FR%3FT%3FR%3FR%3FR%3FP%3FT%3FRARARARARARCRARAPCRCRCRCRCPCREREPCPEREPERGPEPEPGPGPGPGNGPGPGNININGPILIPILINILINKLINKJILKLKLKJKLKJMJKJKJMJKHMHKJMHMHMHMHMFMHMFODMFMFMFODMDMDODODMBODOBMBOBO%40MBO%40O%40OBO%3FM%3FO%40O%3FO%40OAO%3FOAM%3FO%3FOCOAOAMCOAOCOCMCOEMCOEMEOEOEMEMGMGOGMEMGMIMGMIMIMIMIKKMIKIMKKKMKKKKKKMKKKMKMIMKKKOIMIOIMKOGMIQIMIQGMIQGOGQGQIOEQGQGQEQEQGQESEQESCQEQESCSCQCSCSCSCQASCSASASASASASAS%3FS%3FU%3FQ%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=jgC6j1su5knNRIbqRJqXHMmDn1Q=) Annapolis, MD ### What's nearby - ![U.S. Naval Academy featuring military items, interior views and heritage architecture](https://images.trvl-media.com/place/6077390/365a14c8-731b-4cc4-a5d7-9baf0c5edd8f.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) U.S. Naval Academy 12 min drive \- 7.9 km - ![Chesapeake Bay Bridge](https://images.trvl-media.com/place/6077400/6584abf3-a806-4d48-87f3-d73ac35445d0.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Chesapeake Bay Bridge 24 min drive \- 23.1 km - Bay Ridge Beach 6 min walk \- 0.6 km - Annapolis City Dock 12 min drive \- 7.9 km - Westfield Annapolis Mall 16 min drive \- 12.1 km ### Getting around - Odenton Station 28 min drive - Fort Meade, MD (FME-Tipton) 37 min drive ### Restaurants - McDonald's 6 min drive - Bay Ridge Wine & Spirits 6 min drive - Carrol's Creek Cafe 10 min drive - Boatyard Bar & Grill 10 min drive - Starbucks 6 min drive ## Frequently asked questions ### Is Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting pet-friendly? ### How much is parking? ### What time is check-in at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting? ### What time is check-out at Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting? ### Where is Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Cheerful Cottage Home near Annapolis in Beautiful Chesapeake Bay Beach setting Reviews ## Reviews 10 ### Exceptional