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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

A pier with outdoor seating and a covered area, overlooking a body of water. - Lovely bay views with kayaks, bikes, fire pit, crabbing & more (Shady Side)
A living room with a fireplace, white furniture, and a television. - Lovely bay views with kayaks, bikes, fire pit, crabbing & more (Shady Side)
A large bed with a white and blue bedspread, two bedside tables, and a nightstand with a lamp. - Lovely bay views with kayaks, bikes, fire pit, crabbing & more (Shady Side)
A single-story house with a front porch, a small staircase, and a mailbox. - Lovely bay views with kayaks, bikes, fire pit, crabbing & 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 bay views with kayaks, bikes, fire pit, crabbing & more (Shady Side)
Situated in a picturesque water community on the Chesapeake Bay, this 3-bedroom cottage offers a soothing ambiance and plenty of opportunities for fun. Enjoy kayaking, crabbing, or simply hanging out in the fenced-in backyard with your dogs. With two waterfront restaurants nearby and access to numerous parks and marinas, you'll never be short on adventure.

Reviews

9.6 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 898 sq m

Popular amenities

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

Add dates for prices

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 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, 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

Property amenities

Beach

  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV
  • Video games

Outdoor areas

  • Firepit
  • Garden
  • Gas grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay
  • Near the marina

Things to do

  • Arcade/game room
  • Bicycles
  • Kayak
  • Water sports equipment
  • Birdwatching nearby
  • Fishing nearby
  • Kayaking nearby
  • Motor boating nearby

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

  • Bicycles
  • Garden
  • Unit size: 1,050 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Check-out

Check-out before 11:00 AM

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets

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
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 neighborhood

Shady Side is home to this vacation home. Captain Avery Museum and Dr. Aris T. Allen Memorial are local landmarks, and travelers looking to shop may want to visit Annapolis City Dock and Annapolis Harbour 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 grand hall with ornate columns, a large staircase, and flags.
    U.S. Naval Academy
    37 min drive - 41.5 km
  • A park with a walking path, picnic tables, and a large tree. In the background, there is a bridge over a body of water.
    Sandy Point State Park
    44 min drive - 51.6 km
  • Shadyside Park
    2 min drive - 1.4 km
  • Captain Avery Museum
    3 min drive - 2.1 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
  • 7-Eleven
    9 min drive
  • South County Cafe
    11 min drive
  • Pirates Cove Restaurant
    14 min drive
  • Boat House
    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 is parking?

Onsite 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?

Check-out is at 11:00 AM.

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 27 out of 33 reviews
Rating 8 - Good. 5 out of 33 reviews
Rating 6 - Okay. 1 out of 33 reviews
Rating 4 - Poor. 0 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.8

Cleanliness

9.8

Location

10

Property conditions & facilities

Reviews

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
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
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

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

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

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
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

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
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
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
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
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
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
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
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

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

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