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Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Photo gallery for Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Living room with tv and gas fireplace
Game shed with bar, margarita machine, tv, skeeball and Street Fighter game
King size bed in first floor bedroom
Two twin beds and two twin trundle beds in 2nd floor bedroom
Front of house

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Shady Side, MD
  • Place, Shadyside Park
    ‪2 min drive‬
  • Place, Captain Avery Museum
    ‪3 min drive‬
  • Place, U.S. Naval Academy
    ‪37 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪61 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

4 Single Beds

2 bathrooms

Bathroom 1

Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 2

Towels provided · Bathtub or shower · Toilet · Hair dryer

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

About this property

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Charming 3 bedroom, 2 bathroom private cottage is situated in a friendly water 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 near numerous parks and marinas, with plenty of access to fun on the water, 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, 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 and gas grill.

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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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
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 (limit 2 total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3298374vb
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

About the area

Shady Side

Shady Side is home to this holiday home. Captain Avery Museum and The Kunta Kinte Alex Haley Memorial are local landmarks, and travellers looking to shop may want to visit Annapolis Harbour Center and Annapolis Harbor Center Shopping Center. Travelling with kids? Consider Chesapeake Beach Water Park and Chesapeake Beach Railway Museum. With kayaking, power boating and fishing nearby, you'll find plenty of adventures in the water.
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Map
Shady Side, MD

What's nearby

  • Shadyside Park - 2 min drive - 1.4 km
  • Captain Avery Museum - 3 min drive - 2.1 km
  • U.S. Naval Academy - 37 min drive - 41.1 km
  • Annapolis City Dock - 39 min drive - 42.2 km
  • Chesapeake Bay Bridge - 47 min drive - 53.3 km

Getting around

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

Restaurants

  • ‪Bayside Bull - ‬18 min drive
  • ‪7-Eleven - ‬9 min drive
  • ‪Dunkin' - ‬18 min drive
  • ‪Jesse Jay’s - ‬7 min drive
  • ‪Happy Harbor Restaurant - ‬11 min drive

Frequently asked questions

Is Lovely bay views with kayaks, bikes, fire pit, crabbing & more pet-friendly?

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

How much does it cost to stay at Lovely bay views with kayaks, bikes, fire pit, crabbing & more?

As of 10 May 2026, prices found for a 1-night stay for 2 adults at Lovely bay views with kayaks, bikes, fire pit, crabbing & more on 11 May 2026 start from AU$502, 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 Lovely bay views with kayaks, bikes, fire pit, crabbing & more?

On-site parking is available at the property.

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

Check-in begins at 4:00 PM.

What time is check-out at Lovely bay views with kayaks, bikes, fire pit, crabbing & more?

Checkout is at 11:00 AM.

Where is Lovely bay views with kayaks, bikes, fire pit, crabbing & more located?

This family-friendly Shady Side holiday 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 miles (5 km).

Reviews

9.8

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. 25 out of 29 reviews
Rating 8 - Good. 3 out of 29 reviews
Rating 6 - Okay. 1 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.8/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Brian F.

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

10/10 Excellent

Jennifer O.

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

10/10 Excellent

Lauren W.

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
Response from VrboOwner on 23 Mar 2026
We're so happy to hear that the supplies we provide were helpful. That's our goal so we're so happy to hear that you found everything you needed. Thanks for staying with us and we look forward to hosting you in warmer weather!
Verified

10/10 Excellent

Andrew A.

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

10/10 Excellent

Barry C.

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
Response from VrboOwner on 23 Mar 2026
Thanks for staying with us. We greatly appreciate you taking good care of our home and thanks for the helpful feedback.
Verified

10/10 Excellent

Kimberly B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very cute house. We had a wonderful weekend!
Stayed 3 nights in Dec 2025
Response from VrboOwner on 12 Jan 2026
Thanks for leaving a review and for staying with us. It was a pleasure to host you and we were so happy that you had a great stay!
Verified

10/10 Excellent

Brenda A.

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
Response from VrboOwner on 12 Jan 2026
It was such a pleasure to host you while you were visiting. Thanks for being such a wonderful guest and we hope to host you again next time you visit.
Verified

10/10 Excellent

Kristin A.

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
Response from VrboOwner on 8 Oct 2025
Thanks for staying with us Kristin! We enjoyed hosting you and hope you'll stay with us again.
Verified

10/10 Excellent

Patricia M.

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

Chesapeake Bay House

Very nice property, relaxing comforatable stay
Stayed 2 nights in Aug 2024
Response from VrboOwner on 25 Sept 2024
Thanks so much for staying with us Patricia. So happy to hear that you had a nice, relaxing stay.
Verified

10/10 Excellent

Jon M.

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
Response from VrboOwner on 8 Oct 2025
Thanks for the great feedback Jon and for being such a great guest. It was a pleasure to host you!
Verified

10/10 Excellent

megan f.

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
Response from VrboOwner on 8 Oct 2025
We're so glad you and your family and your pup enjoyed your stay. It was our pleasure to host you all!
Verified

10/10 Excellent

Ed H.

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

10/10 Excellent

Farrah W.

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
Response from VrboOwner on 31 Oct 2023
Thanks so much for staying with us Farrah!
Verified

10/10 Excellent

Don S.

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

8/10 Good

Gloria B.

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

Nice small houee

Four seniors visiting Annapolis. House was adequate for our needs. Twenty miles outside Annapolis. Neighborhood quiet.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Maude H.

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

This is an excellent property in a really nice community!

Lovely home, which we appreciate the host sharing with us. The location was excellent. We enjoyed eating in, cooking out, and kayaking. Also a day in Solomons and then in Annapolis. The neighbors are so friendly! House in excellent condition and host is responsive to texts as needed.
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Marta B.

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

Family Weekend

We had a lovely stay. The house was cozy and comfortable. The bikes were perfect for exploring the neighborhood and we loved walking to the dock to fish and kayak. Our two dogs joined us and they had a wonderful time as well. The yard was perfect for them to romp around and have a wonderful time. It was a wonderful weekend.
Stayed 2 nights in Jun 2023
Verified

10/10 Excellent

Stuart L.

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

10/10 Excellent

Matthew

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

8/10 Good

Kelly M.

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

10/10 Excellent

Kayla T.

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

Great Family Retreat

This was a great property for a young family to stay at, with quick access to the bay. Annapolis is very close by, with a lot of restaurants and other locations to visit. The neighborhood was very nice, with friendly neighbors on each side. Everything was very bright outside at night too, with a lot of street lights. (If you have little ones, consider bringing portable black out screens for some windows.) The house was clean and comfortable, with a backyard and game room that teens would likely love. The owners were great and very easy to get a hold of. They were quick to respond and help out. Highly recommended!
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Kathryn C.

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
Response from VrboOwner on 31 Oct 2023
Thanks for choosing to stay with us Katie. We know that the well water smell is different. We've put room darkening curtains in the primary bedroom and queen bedroom so hopefully that helps with morning light.
Verified

6/10 Okay

Kathleen C.

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

8/10 Good

Maria M.

Liked: Check-in, communication, location

Shady Side getaway

Spent four nights at this house near the bay with my husband and our poodle. We loved the proximity to several waterfront restaurants and Annapolis. Had an incredible dinner at Jesse Jay’s Latin Kitchen! The house is cute and the owners provided lots of supplies like beach towels, coffee and paper products which are often NOT provided by other properties. The windows treatments do not keep out the bright street light from the bedroom. The yard needs a lot of work and the photos looked like there was a secure six foot fence around the yard. In reality one section of the fence is low and open picket type. This wouldn’t be a problem for everyone, but we wanted to have a chance to play with our dog off leash (we don’t have a fenced yard at home).
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Carlos M.

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

Great family stay!

We recently visited this home to celebrate my son's 3rd birthday. It was the perfect location for a quick mid-week escape from DC, only an hour from our home but it felt a world away. The house itself is very cute and decorated in a nautical theme. The beds were comfortable and the kitchen had everything we needed for cooking. We brought our little dog and the owners have the house equipped with dog bowls, blankets, and a dog bed that my pup would not leave. I also want to add that as parents of a 2 and 4 year old who get into everything, the home was super child friendly without dangerous decorations or pointy tables etc. The house is located by the water and we could walk to a playground with a private beach that was perfect for my young kids. We were also surprised by how friendly everyone in this area was and enjoyed the seafood at nearby restaurants. Owner was very responsive to my questions and provided a guidebook with suggestions and house rules that made everything very simple! There are kayaks you can use if you wish which we will have to take advantage of on our next trip. We would definitely return!
Stayed 2 nights in Apr 2023
Response from VrboOwner on 14 Aug 2023
Carlos, we were so happy to host you as one of our first guests at our new vacation home. We're so happy that you had such a great stay and loved the area. Thanks so much!

About the host

Hosted by Mary Denby

Host profile image
Hi! We’re Mary and Chris, parents of two college-aged kids and big believers in travel as a way to recharge. When we need a break from our busy lives in Alexandria, VA, we escape to Shady Side and the peaceful beauty of the Chesapeake Bay. We love being able to welcome guests to our home.

Why they chose this property

We love this neighborhood for its friendly people, relaxed vibe, and easy walkability. We love to spend time at the community pier and kayaking out on the water taking in the beauty of the Chesapeake Bay

What makes this property unique

Our home is a cozy retreat with a big backyard where our family slows down, reconnects, and enjoys a quieter pace of life. Our dogs love the spacious fenced in backyard. We’re happy to share it with guests looking for the same kind of escape.

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