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Waterfront Home on the Chesapeake Bay!

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Dining - Waterfront Home on the Chesapeake Bay! (Shady Side)
Marina - Waterfront Home on the Chesapeake Bay! (Shady Side)
Exterior - Waterfront Home on the Chesapeake Bay! (Shady Side)
4 bedrooms, travel crib, free WiFi, bed sheets - Waterfront Home on the Chesapeake Bay! (Shady Side)
Interior - Waterfront Home on the Chesapeake Bay! (Shady Side)
Overlooking the Chesapeake Bay, this West River home offers a serene retreat. Unwind in the sunroom with large sliding doors that welcome the bay breeze or try your hand at crabbing and fishing from the private dock. With a fully stocked kitchen, expansive family room, and offstreet parking for 3 vehicles.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 8

Popular amenities

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

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Waterfront Home on the Chesapeake Bay!

Expansive views of the Cheasapeake Bay, located on the West River this home is private, peaceful and immaculate. Home includes private dock with boat lift, 1 car garage and a large open floor plan.
Large family room over-looks the water with a beautiful Sunroom that has a large sliding door to allow the bay breeze in. Fully stocked kitchen with Kureig/Pot coffee maker and gas stove.
On the upper level you will find 3 large bedrooms. The primary offers beautiful views of the water and is complete with a full ensuite bath. There is a full hallway bath that serves the other two bedrooms. On the main floor you will find the "bunk" room, with a full-size bed on the bottom and a twin up top, with a full hallway bath next to it.
Home offers a large private pier that will allow you to pull right up with your boat. So much to do at this home, crabbing, fishing, paddle-boarding, kayaking, or just relaxing. This property is located just 25 minutes south of Annapolis, and 40 minutes from either downtown DC or Baltimore.
Numerous waterfront restaurants within 10 minutes from the home.
Offstreet parking for 3 vehicles.

Property amenities

Beach

  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Jetted bathtub
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • Near a hospital
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Birdwatching nearby
  • Wildlife walks 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)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden

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    Policies

    Check-in

    Check-in time starts at 4:00 PM
    Minimum check-in age: 25

    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 and a deadbolt lock
    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

    About the neighborhood

    Located in Shady Side, this vacation home is on the waterfront. Captain Avery Museum and The Kunta Kinte Alex Haley Memorial are local landmarks, and the area's natural beauty can be seen at Franklin Point State Park and Smithsonian Environmental Research Center. Looking to enjoy an event or a game while in town? See what's happening at Show Place Arena or Navy-Marine Corps Memorial Stadium. Be sure to check out the area's animals with activities such as game walks and birdwatching. Visit our Shady Side travel guide
    View more Vacation Homes in Shady Side
    Map
    MD, Shady Side

    What's nearby

    • U.S. Naval Academy
      U.S. Naval Academy
      33 min drive - 41.1 km
    • Shadyside Park
      2 min drive - 1.8 km
    • Captain Avery Museum
      3 min drive - 2.1 km
    • Westfield Annapolis Mall
      30 min drive - 37.4 km
    • Annapolis City Dock
      35 min drive - 41.8 km

    Getting around

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

    Restaurants

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

    Frequently asked questions

    Is Waterfront Home on the Chesapeake Bay! 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 Waterfront Home on the Chesapeake Bay!?

    Check-in begins at 4:00 PM.

    What time is check-out at Waterfront Home on the Chesapeake Bay!?

    Check-out is at 11:00 AM.

    Where is Waterfront Home on the Chesapeake Bay! located?

    Situated on the waterfront, this vacation home is within 2 mi (3 km) of Shadyside Park, Captain Avery Museum, and Franklin Point State Park. Chesapeake Bay and Northern Chesapeake Bay are also within 3 mi (5 km).

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    Waterfront Home on the Chesapeake Bay! 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.
    More informationOpens in a new window
    Rating 10 - Excellent. 28 out of 31 reviews
    Rating 8 - Good. 3 out of 31 reviews
    Rating 6 - Okay. 0 out of 31 reviews
    Rating 4 - Poor. 0 out of 31 reviews
    Rating 2 - Terrible. 0 out of 31 reviews

    10

    Cleanliness

    9.4

    Location

    Reviews

    Verified

    10/10 Excellent

    Roxanne K.

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

    Awesome stay

    The property was even bigger than we imagined and we had a wonderful quiet vacation looking at the water and going to museums.
    Stayed 6 nights in Aug 2023
    Verified

    8/10 Good

    Stacie P.

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

    Nice

    Great location and nice rental.
    Stayed 6 nights in Aug 2023
    Verified

    10/10 Excellent

    Parker N.

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

    Amazing property - central location

    We were expecting the usual rental accommodations so were blown away by the homes newly renovated open floor plan, spectacular waterfront view and central location to DC, Annapolis and Alexandria. We had a magnificent time.e bedrond LRs
    Stayed 4 nights in Dec 2024
    Verified

    10/10 Excellent

    Richard R.

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

    Family Easter weekend

    The views from the primary bedroom, enclosed porch (with outdoor dining for 8 and great room were beautiful!Kitchen was large and well equipped. Neighbors were friendly.Close to Annapolis.Would return in the future.
    Stayed 3 nights in Apr 2025
    Verified

    10/10 Excellent

    Mike H.

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

    Great place, great location

    The house and property are beautiful. We brought our boat with us and made trips to Annapolis and Kent Narrows. If you’re looking for a place that is quiet, has great views, but is centrally located, then consider this as homebase.
    Stayed 3 nights in May 2024
    Verified

    10/10 Excellent

    Stevie A.

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

    Beautiful Views!

    We had an amazing time here. The house was great, the views amazing. The yard was perfect for our child and dog to play around on. We loved being able to use the kayaks and were sad to leave! Would definitely stay again!
    Stayed 4 nights in Jul 2023
    Verified

    10/10 Excellent

    Derek B.

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

    Right place and right time

    Thrilled to stay here with my family. We all enjoyed this waterfront home together and we will cherish the memory. I would like to thank the host for making it all possible.
    Stayed 6 nights in Aug 2024
    Verified

    10/10 Excellent

    Lisa K.

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

    Something For Everyone

    The house was clean, nicely decorated and comfortable. Fishing, boating and biking were enjoyed by all ages.
    Stayed 4 nights in Jul 2023
    Verified

    8/10 Good

    Amena S.

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

    Beautiful house that feels like a home!

    We spent 3 nights and 4 days here and had a very comfortable stay . The house was clean and well maintained and had everything that we needed, even an umbrella to protect our daughter from sun when sitting at the water. The covered patio was a plus to spend time in the morning. Really appreciated the water filter and complimentary coffee in the kitchen.
    Stayed 3 nights in Jul 2023
    Verified

    10/10 Excellent

    C H.

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

    Another Wonderful Holiday Stay!

    We loved this home so much last year that we booked again this year for another peaceful family Thanksgiving getaway. The house is well supplied with everything we needed, and the sun porch facing the water provided seating that allowed us to watch the sunset as we enjoyed each other's company. It's tucked away in a quiet neighborhood off the beaten path, just what we needed to step away from our busy lives to rest. Easy check in and check out, immaculately clean.
    Stayed 4 nights in Nov 2023
    Verified

    10/10 Excellent

    Claire S.

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

    Beautiful retreat

    We loved our stay here! The views are incredible and the house is wonderfully decorated. The only thing I would note is that the water heater seemed to be on demand, so if people are showering at the same time you will lose hot water. A simple "turn off-turn on" fixed it right up, and it saves water! Our group would love to come back in the summer, I'm sure its lovely.
    Stayed 3 nights in Dec 2023
    Verified

    10/10 Excellent

    Elizabeth D.

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

    Relaxation in Shady Side

    The property manager was great at answering questions and offered prompt & courteous assistance. The house was exactly as described, and we really appreciated the toys & books for young children. We enjoyed the dock - we fed the fish with the worms on our hooks! Didn't catch any fish but had fun. The nearby swim area and playground was a 2 minute walk for the kids. We are already talking about coming back!
    Stayed 7 nights in Jul 2024
    Verified

    10/10 Excellent

    Wes L.

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

    Couldn’t be better!

    We arrived after a 17 hour travel nightmare from the mountains of Colorado. Had a two year old and four year old in tow who were very cranky from the journey. We needed the house to be just right and it overperformed in every way. The view is amazing, the house is very clean, everything worked and was well organized. We had some family down from Annapolis and everyone was so impressed. Couldn’t have had a better time. Look forward to visiting again in the future. Very cool neighborhood and a gem of a house.
    Stayed 4 nights in Nov 2024
    Verified

    10/10 Excellent

    Joe B.

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

    Labor Day Weekend Getaway

    Property was as expected based on the listing, property manager very responsive. Location was perfect with a nice size backyard and dock for the kids to enjoy. Beautiful sunset view. Beds were comfortable and more then enough room for 2 families with multiple kids each. Property had onsite cornhole, bikes, and other amenities we weren’t expecting. Kids love to take the kayaks out into the cove and fish off the dock. House was super clean. We loved it so much we are thinking of making this an annual trip with our friends and their family. What an amazing Oasis local to the DMV. Who knew such existed. Definitely will be back.
    Stayed 3 nights in Sep 2023
    Verified

    10/10 Excellent

    Jackie C.

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

    Good relaxation for a Navy midshipmen and family

    Very nice getaway for a family reunion group of 8 while we visited our son at the USNA. Location is 35 min from US Naval academy; perfect to feel like he's really getting off the Yard. Having such a huge yard really offered lots to do (corn hole, frisbee, etc.). The incredible water views drew us all back home every night, along with the gorgeous sunsets. Had really nice weather so we took advantage of the 3 kayaks and paddled around the marina. Bikes were convenient too, as well as small playground 2 houses down. Dock is large, sturdy and fun to fish off of, although we didn't catch anything. House is spacious, clean, roomy and well decorated. Appreciated the info binder which gave great restaurant recommendations. 10 min drive to large grocery store, 5 min to beer & ice store. Neighborhood is family oriented and very quiet. We really felt we were getting away from it all and living the "water life". Thank you!
    Stayed 5 nights in Oct 2024
    Verified

    10/10 Excellent

    Wade C.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    Great home with lots of room.
    Stayed 8 nights in Nov 2025
    Verified

    10/10 Excellent

    Kenneth D.

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

    Quiet place to relax

    Very nice and friendly community very peaceful and serene. Enjoyed our stay very much.
    Stayed 4 nights in Apr 2023
    Verified

    10/10 Excellent

    Erik Z.

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

    Great place to stay

    This was an ideal setup for our family. Multiple bedrooms, bathrooms, and plenty of space to stretch out. Backyard and location on the water was fantastic. Loved watching the sunset over the water each night. Would stay here again in a heartbeat!
    Stayed 8 nights in May 2023
    Verified

    10/10 Excellent

    Subir D.

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

    Wonderful weekend getaway

    The house was very nice and comfortable sitting nicely along the bay. The backyard of the house has some amazing views of the bay. The house is at half an hour drive to Annapolis and Sandy point state park. There are a lot of restaurant options at 15 min drive from the house. The house was very clean and we enjoyed our stay at the house.
    Stayed 3 nights in Apr 2023
    Verified

    10/10 Excellent

    Fred M.

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

    Happy New Year

    Our family thoroughly enjoyed our New Years together in this welcoming home. Kitchen and dining area well appointed, very clean and comfortable. GREAT location to many activities incl Washington D.C., Annapolis etc. Weather cooperating made the location even better !!!!Owner is really interested in making sure our stay a success.
    Stayed 6 nights in Dec 2022
    Verified

    10/10 Excellent

    Justin Z.

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

    Amazing property!

    Our family enjoyed a wonderful week here. The house was very spacious, clean and comfortable. Even better than the photos. Our nine year old loved the dock, bunk room and big bath upstairs. Crabbing and fishing was a blast! Host was phenomenal and went out of his way to make our stay amazing. Several great restaurants within 15-30 minutes of the house. Lots of great historical places to visit within one to two hours.
    Stayed 7 nights in Jun 2023
    Verified

    10/10 Excellent

    Deborah S.

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

    Happy Gathering

    We really enjoyed staying here. Perfect size and very clean. Amazing master suite overlooking the water. Love that it had a porch, deck and chairs to enjoy the water view. Only suggestion would be to put grab bars in all the showers. We are senior citizens with one handicapped, so really need it. Overall, loved it! Thank you.
    Stayed 4 nights in May 2023
    Verified

    10/10 Excellent

    Russ G.

    Liked: Cleanliness, check-in, location, listing accuracy
    Disliked: Communication

    Great

    The only problem was the dorr key information we had people coming in form Panama.New York and Boston Did not get the key in time to send before the plane left Asked and got no repones till about 1300 on the day we arrived.
    Stayed 5 nights in Oct 2023
    Verified

    10/10 Excellent

    Vicki D.

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

    Perfect Bridal Shower weekend

    We rented the property for My Daughter’s Bridal Shower weekend so that we could all be together. The house was perfect with the most beautiful sunsets! The windows at the back of the house in the family room and in the Master bedroom allow the sunlight in with expansive views of the water. We did not want to leave! The house is very well equipped with everything that you need to cook a large family meal. The property Manager is awesome and she responded very quickly. I loved this house and would definitely rent it again. Also- for anyone that needs a reference of where the property is located- you are only 25 minutes to Annapolis and less than 20 minutes to Dunkirk in Calvert County .This property is also close to enough to DC and Baltimore if you want to do some sightseeing in addition to relaxing on the water. I would highly recommend planning to spend time here just relaxing and enjoying the beautiful sunsets!!
    Stayed 4 nights in Apr 2023
    Verified

    10/10 Excellent

    Daniel W.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    Great house and a boaters dream with a wonderful view on top of it all! House is clean and sizeable. Many amenities are included so you don't have to bring much even though we did! :-) Nice bulkheaded lot with good dock and boat lift. There is a community boat ramp 4 doors down and we put our 21' boat and jetskis in there no problem. We brought 4 kayaks to go along with the 3 they have. They also had a couple bikes to enjoy. Quick access to the Chesapeake and fun local dock and dine restaurants and bars. Good tennis courts near by at Shady Side park. Close by boat to Annapolis, the multiple rivers and even up to Sandy Point state park. You will not run out of things to do nearby. As far as the house, we had use of the 1 car garage and enough parking for our 3 cars and trailers. Showers were good with plenty of hot water. Washer and dryer are newer and were put to good use. Yard is fenced in and our dogs had the freedom to move about. The back enclosed porch had nice views and we ate most all meals at the long table. Smart TV's kept me entertained for the 5 minutes before I fell unconscious from the days activities :-) Grill was available for use as well and worked nicely. A fire pit would be a nice addition...we brought our own. as well as patio blocks, 1/2 cord of wood, and chairs but the fun we had at night enjoying the view, listening to music and toasting marshmallows was well worth the effort. It was a great family bonding time. Shady Side is a great spot to vacation.
    Stayed 8 nights in Aug 2025