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Lovely home in bay community with kayaks, bikes, fire pit, & more

Photo gallery for Lovely home in bay community with kayaks, bikes, fire pit, & more

A living room with a fireplace, white furniture, and a television. - Lovely home in bay community with kayaks, bikes, fire pit, & more (Shady Side)
Two wicker chairs with striped pillows, a small table with a muffin and a mug, and a straw hat on the floor. - Lovely home in bay community with kayaks, bikes, fire pit, & more (Shady Side)
A single-story house with a front porch, a small staircase, and a mailbox. - Lovely home in bay community with kayaks, bikes, fire pit, & more (Shady Side)
A modern living room with a white sectional sofa, a wooden coffee table, and a dining area with a kitchen in the background. - Lovely home in bay community with kayaks, bikes, fire pit, & more (Shady Side)
A large bed with a white and blue bedspread, two bedside tables, and a nightstand with a lamp. - Lovely home in bay community with kayaks, bikes, fire pit, & more (Shady Side)
Take advantage of a firepit, a garden, and a playground at Lovely home in bay community with kayaks, bikes, fire pit, & more. Adventurous travelers may like the bicycling and kayaking at this vacation home. 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 an arcade/game room and laundry facilities.

Reviews

9.6 out of 10
Exceptional

Popular amenities

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

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About this property

Lovely home in bay community with kayaks, bikes, fire pit, & more

  • Charming three bedroom, two bathroom private cottage is situated in a friendly community along the beautiful Chesapeake Bay.

    Take advantage of all the Chesapeake Bay has to offer during your stay. We provide kayaks and supplies for crabbing. The home is located across the street from the water with plenty of access to fun on the water, near numerous parks and marinas, or hang out in the fenced in backyard, perfect for your dogs to visit with you. The home is also right across the waterway from two waterfront restaurants and a short drive to Deale where there are numerous waterfront restaurants and marinas. We are also a close drive to Annapolis and Washington DC.

    Enjoy the updated, soothing ambiance, back deck, firepit, gas fireplace, stand up arcade game, skeeball, kayaks, paddle boat, bikes and more. Perfect get away anytime of the year!

    The house has one bedroom and a full bathroom on the lower entry level. There’s also a washer and dryer on that level available for guest use. The second floor has two bedrooms and a second full bathroom.

    The primary bedroom has a door out to the back deck. Enjoy the outdoor dining table, gas grill or wood burning firepit.

    We have well water that it filtered and disinfected with two different filtration systems. We provide bottled water that you can use to drink and cook with although the tap water is safe to consume. If you have not used well water before, please note that it can have a sulfur smell.

    Anne Arundel short term residential license number STR00674

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About the neighborhood

Shady Side is home to this vacation home. Captain Avery Museum and The Kunta Kinte Alex Haley Memorial are local landmarks, and travelers looking to shop may want to visit Annapolis City Dock and Annapolis Harbor Center Shopping Center. Traveling with kids? Consider Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. With kayaking, motor boating, and fishing nearby, you'll find plenty of adventures in the water. Visit our Shady Side travel guide
View more Vacation Homes in Shady Side
Map
Shady Side, MD

What's nearby

  • A large building with ornate architecture, a cannon, and a sign reading "Bancroft Hall".
    U.S. Naval Academy
    38 min drive - 41.5 km
  • A large suspension bridge over a body of water with a sandy beach in the foreground.
    Chesapeake Bay Bridge
    47 min drive - 53.6 km
  • Shadyside Park
    2 min drive - 1.4 km
  • Navy-Marine Corps Memorial Stadium
    36 min drive - 40.4 km
  • Annapolis City Dock
    40 min drive - 42.5 km

Getting around

  • Bowie State Station
    44 min drive
  • Fort Meade, MD (FME-Tipton)
    46 min drive

Restaurants

  • Bayside Bull
    18 min drive
  • Boat House
    11 min drive
  • South County Cafe
    11 min drive
  • 7-Eleven
    9 min drive
  • Pirates Cove Restaurant
    14 min drive

Frequently asked questions

Is Lovely home in bay community with kayaks, bikes, fire pit, & more pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking?

Onsite parking is available at the property.

What time is check-in at Lovely home in bay community with kayaks, bikes, fire pit, & more?

Check-in begins at 4:00 PM.

What time is check-out at Lovely home in bay community with kayaks, bikes, fire pit, & more?

Check-out is at 11:00 AM.

Where is Lovely home in bay community with kayaks, bikes, fire pit, & more located?

This family-friendly Shady Side vacation home is within 2 mi (3 km) of Shadyside Park, Franklin Point State Park, and Captain Avery Museum. Chesapeake Bay and Northern Chesapeake Bay are also within 3 mi (5 km).

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Reviews

Lovely home in bay community with kayaks, bikes, fire pit, & more Reviews

9.6

Exceptional

9.8

Cleanliness

9.6

Location

10

Property conditions & facilities
Rating 10 - Excellent. 36 out of 44 reviews
Rating 8 - Good. 6 out of 44 reviews
Rating 6 - Okay. 2 out of 44 reviews
Rating 4 - Poor. 0 out of 44 reviews
Rating 2 - Terrible. 0 out of 44 reviews

Reviews

Verified review

6/10 Okay

Liked: Cleanliness, check-in, location, listing accuracy
Property was very nice and our dog enjoyed the fenced in back yard. The house was very clean and spotless.
Stayed 14 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Bright clean beach house in a nice family-friendly and pet-friendly neighborhood. We really appreciated the large fenced-in backyard and being supplied with bottled water and the thoughtful dog basket. The beach house was perfect for two couples. The driving distance between the house and dining & entertainment options was comfortable. We appreciated the messages from our hosts - perfect mix of information and frequency. Thank you for the opportunity to stay at your beach house!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chesapeake Bay House

Very nice property, relaxing comforatable stay
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot for us

The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location.
Stayed 10 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend Away

Very clean, everything as described. Awesome host, communication an A+. Would definitely stay again, if we are in the area.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful home

We had a great stay in this beautiful property. Three good size bedrooms and two nice baths. Well equipped kitchen and nice living area. Large yard for kids or dogs and just relaxing. Convenient to restaurants and markets. Hope to visit again soon.
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean and comfortable

This property was awesome. The house was so clean and well stocked. The kitchen had everything we needed. The appliances are new and not a thing was out of place. They even had a dog bed and supplies for our dog. The owners were very accessible and reached out to make sure we had everything we needed. The neighbors were very friendly and it is a really special place. We will seek this place out if we ever return to Shady Side.
Stayed 7 nights in Jan 2024
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Shady Side Stay

We had a great time in Shady Side relaxing, taking a boat ride and playing on jet skis. We even found a really great ice cream shop right by the house. The house was clean and comfortable. The only downside was the water was not potable and very sandy. The owners did provide a water cooler which was definitely needed. Shady Side is a great place to escape the hustle and bustle of everyday life!
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Great little house! The fenced in yard for pets is absolutely perfect. Fully stocked kitchen, plenty of supplies like paper towels, soap, TP, even condiments and coffee filters. There's a grocery store down the street, and Annapolis is about 30 minutes away. People may have issues with the water, but the owners provide a fancy bubbler so you're more than covered. Neighborhood seems nice and access to the bay is a short stroll down the street. We had a great visit. Thanks Mary and Chris!
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Comfy home

Met up with a friend from college and had a great visit for a few days. House was comfortable and clean. Mary & Chris were very responsive as well. We enjoyed sitting outside in the back yard and letting the dog explore and enjoy being off leash. Quiet neighborhood and beautiful area. Short drive into Annapolis as well. There were really only 2 downsides 1 - the water and the sulphur smell really made it hard to shower or wash dishes but that’s nothing that can be changed and we dealt with it 2 - the curtains don’t block out the street lights or the very early morning sun Overall we had a great stay and would definitely consider staying here again if we visit the area!
Stayed 3 nights in Oct 2023
Verified review

6/10 Okay

Liked: Cleanliness, check-in

Comfortable home for small family group

The home was well appointed with basic amenities provided. It was clean. We were 4 adults and 2 12 yr olds. It is a bit small for that many to spend any more than short periods of time. The kitchen was a bit small for preparing anything other than basic meals. The owners did respond to questions and concerns. The well water was a distraction and although bottled water was provided it was still an inconvenience not being able to use the tap water. The location was convenient to Annapolis and Crofton and DC, areas we needed to get to.
Stayed 4 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable.
Stayed 3 nights in Aug 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a nice time at the house, but it was not exactly like the pictures showed. The house was clean except for the floors, which we contacted the host with our concerns. The host was quick to respond. The kitchen had all necessities and a nice large picnic-type table for meals. Since drinking tap water was discouraged, there was a water machine/dispenser with a jug below.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great host and we enjoyed our stay!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really enjoyed the walks and water views.
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute little house with a lakeside theme. Fit our family of 5 perfectly! Hosts checked in with us via the app during our stay to make sure everything was to our liking. We didn’t have any issues during our stay, but it was nice knowing they would have been very responsive if we needed them! Highly recommend this property!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The hosts are lovely and so kind and really made us feel welcomed! Everything is as described and our girls trip was excellent with their recommendations of things to do and their home is a great place e to gather! We would be back for sure!!!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a great home base for exploring the Chesapeake Bay Area. In all the rentals we’ve ever stayed at, this one was the most generous in stocking supplies for us to use and they were also the most welcoming to our dog. We’d love to visit again during warmer weather so we can enjoy that beautiful backyard.
Sadly this was our only day of sunshine as we arrived. Would have loved to grill and eat outside.
Our winter visit included snow. It still was lovely to be in a cozy space together.
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very cute house. We had a wonderful weekend!
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a quiet neighborhood with friendly neighbors. Very did friendly as well!
Stayed 28 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean with modern decor. Owners were attentive and gave detailed instructions for check-in and check-out. Plenty of beds and extra sheets, blankets and towels. Large dining table for game nights. Additional game shed/man cave in the back yard. Very nice property in a cute area with views of the water. Highly recommend!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Was a great stay. Was on a work detail and needed something close to elderly parents and work. Coo k ed every night with all needed to achieve dinner. Thx again. JBCAIN
Stayed 28 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Get Away

Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay.
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute place!

Great for families and friends. 30 Minute drive to Annapolis.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great little spot in Shady Side

We had a great time with our family and another family plus our new pup! The house is very dog friendly and the fenced in yard was key. Everyone we met in the neighborhood and Shadyside was so friendly.
Stayed 3 nights in May 2025