Shady Side Rentals USA Maryland Shady Side

Waterfront Home on the Chesapeake Bay! | House in Shady Side

9.8 (29 Reviews) |   Pet Friendly   4 Bedrooms  3 Bathrooms  8 Guests
Shady Side House | Waterfront Home on the Chesapeake Bay!

4 Bedroom House in Shady Side

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.

Waterfront Home on the Chesapeake Bay! is located in Shady Side. Waterfront Home on the Chesapeake Bay! provides accommodation, featuring TV, Ocean View, Fireplace/Heating, among other amenities. This House features TV, Ocean View, Fireplace/Heating, to make your stay a comfortable one.

Waterfront Home on the Chesapeake Bay! has 4 Bedrooms , 3 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Shady Side has interesting places to visit. If you want to learn more about the House in Shady Side, such as places to visit and things to do nearby, you can check below to learn more.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Fireplace/Heating
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
Read More Read Less

Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 11:00 am
Child Policy Children are welcome.
Pet Policy 2 total pets pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Shady Side, 20764, USA

What Our Guests say 500 + Reviews

Apr 21, 2025 11:16:37 PM
Summary: 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.
Richard R. Richard R.
Jan 1, 2025 06:32:59 AM
Summary: 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
Parker N. Parker N.
Nov 27, 2024 02:15:15 AM
Summary: 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.
Wes L. Wes L.
Oct 16, 2024 09:47:56 AM
Summary: 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!
Jackie C. Jackie C.
Aug 30, 2024 12:44:51 AM
Summary: 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.
Derek B. Derek B.
Aug 13, 2024 09:47:41 PM
Summary: 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!
Elizabeth D. Elizabeth D.
Jun 3, 2024 10:42:34 PM
Summary: 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.
Mike H. Mike H.
Jan 12, 2024 11:58:48 PM
Summary: 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.
Claire S. Claire S.
Nov 29, 2023 10:20:13 AM
Summary: 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.
C H. C H.
Oct 18, 2023 01:44:03 AM
Summary: 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.
Russ G. Russ G.

FAQ's

Is this Shady Side house pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Shady Side house have a swimming pool?

No, this Shady Side house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Shady Side house?

Best-rates for the Shady Side house starts from $470 per night with includes Ocean View, Fireplace/Heating, View, Security/Safety, Sports/Activities, Internet, Laundry, Hot Tub, Balcony/Terrace, Bedding/Linens, Kitchen, Barbecue/Outdoor Cooking, Child Friendly, Air Conditioner, Parking, Pet Friendly, TV StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Shady Side house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Shady Side house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Shady Side house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Shady Side house?

Based on the information reported by the owner or manager, the Shady Side house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Shady Side house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Shady Side house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

People Also Ask

Check House Availability
Nightly rates from:
US $470
Price Details
You will be redirected to  
Hot Deal - It has been viewed 49 times today
Not the right fit? Check out our other properties in Shady Side
9.6 (7 Reviews)
House
Calloway Drive Retreat
  • View
  • Wheelchair Accessible
  • Balcony/Terrace
View Availability
8.0 (12 Reviews)
Apartment
Chesapeake Bayside Loft
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
view more places to stay

Recently Booked Locations

Recently Booked Properties