Airbnb Properties for Sale in Shady Side, MD

Looking for a vacation rental investment in Shady Side, MD with high ROI ?

Explore a range of newly added short-term rental homes in Shady Side, MD. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Shady Side, MD

Q: How many Airbnb properties are available for sale in Shady-side?

There are 13 Airbnb properties available for sale in Shady-side

Q: What is the average Airbnb occupancy rate in Shady-side, MD?

In October 2026, the average Airbnb occupancy rate in Shady-side is 28%.

Q: How to get Shady-side, MD Airbnb data?

Airbnb data on vacation rentals in Shady-side, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Shady-side, MD market insights, guest information and booking details, seasonality trends and historical Shady-side, MD Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4721 Oak Rd Shady Side, MD Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking...	4 beds \| 3 baths \| 1,868 sq.ft.	$998,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.87% Airbnb Rental Income: $3702 Traditional Rental Income: $2526 Airbnb ROI: 1.27% Traditional ROI: 0.87%
1704 Maryland Ave Shady Side, MD PRICE REDUCED! Chesapeake Waterview/access with Your Very Own Dock. Property Consists of S...	4 beds \| 2 baths \| 1,930 sq.ft.	$330,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 6.14% Airbnb Rental Income: $3702 Traditional Rental Income: $2656 Airbnb ROI: 6.88% Traditional ROI: 6.14%
1316 Azalia St Shady Side, MD Move in condition & 100% financing approved (USDA Loan). Very well maintained home in a wa...	3 beds \| N/A baths \| 1,500 sq.ft.	$465,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 2.07% Airbnb Rental Income: $2366 Traditional Rental Income: $1691 Airbnb ROI: 2.28% Traditional ROI: 2.07%
1221 Bast Ln Shady Side, MD Almost 1 acre of land with water views! Wood burning fireplace! Large detached garage! Se...	4 beds \| 2 baths \| 2,089 sq.ft.	$625,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.45% Airbnb Rental Income: $3702 Traditional Rental Income: $2424 Airbnb ROI: 3.26% Traditional ROI: 2.45%
1411 Haile Pkwy Shady Side, MD Rivendale Homes introduces the Cedarbury house type to Shady Side! This gorgeous custom bu...	4 beds \| 3 baths \| 1,905 sq.ft.	$525,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 4.34% Airbnb Rental Income: $3702 Traditional Rental Income: $2755 Airbnb ROI: 4.62% Traditional ROI: 4.34%
1199 OAK AVE Shady Side, MD Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhur...	4 beds \| 2 baths \| N/A	$399,900	Airbnb cash on cash: 5.56% Traditional cash on cash: 5.27% Airbnb Rental Income: $3702 Traditional Rental Income: $2786 Airbnb ROI: 5.56% Traditional ROI: 5.27%
1220 Grove Ave Shady Side, MD Welcome to the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shad...	5 beds \| 2 baths \| 1,812 sq.ft.	$465,000	Airbnb cash on cash: 6.57% Traditional cash on cash: 4.75% Airbnb Rental Income: $4684 Traditional Rental Income: $2922 Airbnb ROI: 6.57% Traditional ROI: 4.75%
5314 Al Jones Dr Shady Side, MD Home is ready for immediate occupancy. Ask about 3.99% for FHA & VA loans. Coastal Living ...	4 beds \| 2 baths \| 2,710 sq.ft.	$619,990	Airbnb cash on cash: 2.76% Traditional cash on cash: -0.91% Airbnb Rental Income: $3702 Traditional Rental Income: $771 Airbnb ROI: 2.76% Traditional ROI: -0.91%
1582 Snug Harbor Rd Shady Side, MD 1582 Snug Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 1,915 sq.ft.	$599,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 1.82% Airbnb Rental Income: $3702 Traditional Rental Income: $2280 Airbnb ROI: 2.92% Traditional ROI: 1.82%
1183 Cedar Ave Shady Side, MD Professional pictures coming!! Rarely available and proudly offered for the first time, th...	4 beds \| 3 baths \| 1,964 sq.ft.	$499,900	Airbnb cash on cash: 3.85% Traditional cash on cash: 3.42% Airbnb Rental Income: $3702 Traditional Rental Income: $2686 Airbnb ROI: 3.85% Traditional ROI: 3.42%
1194 Oak Ave Shady Side, MD 1194 Oak Ave, Shady Side, MD 20764 \| Single Family Residential	5 beds \| 4 baths \| 2,680 sq.ft.	$499,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 4.33% Airbnb Rental Income: $4684 Traditional Rental Income: $3087 Airbnb ROI: 5.68% Traditional ROI: 4.33%
5314 Al Jones Rd Shady Side, MD 5314 Al Jones Rd, Shady Side, MD 20764 \| Single Family Residential	4 beds \| 2 baths \| 2,710 sq.ft.	$599,990	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.03% Airbnb Rental Income: $3702 Traditional Rental Income: $2473 Airbnb ROI: 2.76% Traditional ROI: 2.03%

Vacation Rentals in Shady Side

There are 13 vacation rental properties available for sale in the city of Shady Side . The median list price of Airbnb properties available for sale in Shady Side is $468,719 and the average price per square foot is $233. The cash on cash return on vacation rentals in Shady Side is 3.00%. The average monthly short term rental income in Shady Side is $2,366.

Shady Side, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 13 Airbnb properties available for sale in Shady Side.

In 2026, the best neighborhood to buy short term rental property is Shady Side.

In October 2026, the average Airbnb occupancy rate in Shady Side is 28%.

Airbnb data on vacation rentals in Shady Side, MD is available at Mashvisor. You can access data such as listings, real-time pricing trends, Shady Side, MD market insights, guest information and booking details, seasonality trends and historical Shady Side, MD Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Shady Side, MD

4721 Oak Rd

Shady Side, MD

4 beds | 3 baths | 1,868 sq.ft.

$998,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $3702

Traditional Rental Income: $2526

Airbnb ROI: 1.27%

Traditional ROI: 0.87%

1704 Maryland Ave

Shady Side, MD

4 beds | 2 baths | 1,930 sq.ft.

$330,000

Airbnb cash on cash: 6.88%

Traditional cash on cash: 6.14%

Airbnb Rental Income: $3702

Traditional Rental Income: $2656

Airbnb ROI: 6.88%

Traditional ROI: 6.14%

1316 Azalia St

Shady Side, MD

3 beds | N/A baths | 1,500 sq.ft.

$465,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 2.07%

Airbnb Rental Income: $2366

Traditional Rental Income: $1691

Airbnb ROI: 2.28%

Traditional ROI: 2.07%

1221 Bast Ln

Shady Side, MD

4 beds | 2 baths | 2,089 sq.ft.

$625,000

Airbnb cash on cash: 3.26%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $3702

Traditional Rental Income: $2424

Airbnb ROI: 3.26%

Traditional ROI: 2.45%

1411 Haile Pkwy

Shady Side, MD

4 beds | 3 baths | 1,905 sq.ft.

$525,000

Airbnb cash on cash: 4.62%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $3702

Traditional Rental Income: $2755

Airbnb ROI: 4.62%

Traditional ROI: 4.34%

1199 OAK AVE

Shady Side, MD

4 beds | 2 baths | N/A

$399,900

Airbnb cash on cash: 5.56%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $3702

Traditional Rental Income: $2786

Airbnb ROI: 5.56%

Traditional ROI: 5.27%

1220 Grove Ave

Shady Side, MD

5 beds | 2 baths | 1,812 sq.ft.

$465,000

Airbnb cash on cash: 6.57%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $4684

Traditional Rental Income: $2922

Airbnb ROI: 6.57%

Traditional ROI: 4.75%

5314 Al Jones Dr

Shady Side, MD

4 beds | 2 baths | 2,710 sq.ft.

$619,990

Airbnb cash on cash: 2.76%

Traditional cash on cash: -0.91%

Airbnb Rental Income: $3702

Traditional Rental Income: $771

Airbnb ROI: 2.76%