Airbnb Properties for Sale in Chicago, MD

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

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

Airbnb For Sale in Chicago, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Chicago, Maryland at the moment.
Other Airbnb Properties for Sale in Maryland
1520 BYRD Street Baltimore , MD Welcome home to 1520 Byrd Street! This beautifully updated four level with 3/4bedroom, 3-f...	4 beds \| 3 baths \| 1,571 sq.ft.	$480,000	Airbnb cash on cash: 5.4% Traditional cash on cash: 3.18% Airbnb Rental Income: $4607 Traditional Rental Income: $2653 Airbnb ROI: 5.4% Traditional ROI: 3.18%
2234 FLEET Street Baltimore , MD Welcome to 2234 Fleet St! Nestled in the vibrant Baltimore neighborhood of Canton but just...	3 beds \| 2 baths \| 1,754 sq.ft.	$325,000	Airbnb cash on cash: 5.31% Traditional cash on cash: 3.79% Airbnb Rental Income: $3328 Traditional Rental Income: $2120 Airbnb ROI: 5.31% Traditional ROI: 3.79%
1320 Fenwick Ln #711 Silver Spring , MD Set in the heart of downtown Silver Spring, this stylish condo offers an exceptional blend...	1 beds \| 1 baths \| 549 sq.ft.	$275,000	Airbnb cash on cash: 6.34% Traditional cash on cash: 3.99% Airbnb Rental Income: $2892 Traditional Rental Income: $1610 Airbnb ROI: 6.34% Traditional ROI: 3.99%
3200 N LEISURE WORLD Boulevard unit: 514 #514 Silver Spring , MD ENJOY THE NEXT PHASE OF YOUR LIFE IN THIS BRIGHT, GRACIOUS APARTMENT OVERLOOKING TREES AND...	2 beds \| 2 baths \| 1,035 sq.ft.	$250,000	Airbnb cash on cash: 4.62% Traditional cash on cash: 3.55% Airbnb Rental Income: $3070 Traditional Rental Income: $2118 Airbnb ROI: 4.62% Traditional ROI: 3.55%
15107 Interlachen Dr #2-815 Silver Spring , MD Nestled within the prestigious Greens at Leisure World, this large and roomy 2-bedroom, 2-...	2 beds \| 2 baths \| 1,120 sq.ft.	$215,000	Airbnb cash on cash: 9.25% Traditional cash on cash: 7.89% Airbnb Rental Income: $3070 Traditional Rental Income: $2094 Airbnb ROI: 9.25% Traditional ROI: 7.89%
413 ROBIN Drive unit: A305 #A305 Ocean City , MD Your Beachside Retreat or Investment Starts Here! Discover the perfect blend of comfort, l...	2 beds \| 1 baths \| 792 sq.ft.	$259,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 1.91% Airbnb Rental Income: $1863 Traditional Rental Income: $1361 Airbnb ROI: 1.92% Traditional ROI: 1.91%
7819 Bertha Rd Pasadena , MD Property is Vacant. Interior and exterior inspections available and the property is being ...	3 beds \| 1 baths \| 1,276 sq.ft.	$350,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 2.89% Airbnb Rental Income: $3077 Traditional Rental Income: $1626 Airbnb ROI: 5.17% Traditional ROI: 2.89%
3210 N Leisure World Blvd #610 Silver Spring , MD AS IS 55+ Community, J Model. Beautiful sapcious 3 bedroom unit with ease of access to the...	3 beds \| 2 baths \| 1,550 sq.ft.	$350,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 4.59% Airbnb Rental Income: $3882 Traditional Rental Income: $2329 Airbnb ROI: 6.77% Traditional ROI: 4.59%
800 Baltimore Annapolis Blvd Severna Park , MD Assumable! 2.99% rate. Call for details. This conveniently located Split level home has ju...	4 beds \| 4 baths \| 2,490 sq.ft.	$699,900	Airbnb cash on cash: 4.9% Traditional cash on cash: 3.11% Airbnb Rental Income: $5672 Traditional Rental Income: $3374 Airbnb ROI: 4.9% Traditional ROI: 3.11%
304 Forest Ct Severna Park , MD Bright, turnkey home. Exceptional privacy with a tree-house feel in back. Oak Flooring thr...	4 beds \| 2 baths \| 2,132 sq.ft.	$749,900	Airbnb cash on cash: 4.78% Traditional cash on cash: 1.53% Airbnb Rental Income: $5672 Traditional Rental Income: $2268 Airbnb ROI: 4.78% Traditional ROI: 1.53%
6159 Fishers Station Rd LOTHIAN , MD BEAUTIFUL RANCHER WITH OVER 2800 SQUARE FEET OF LIVING SPACE! MAIN LEVEL HAS 3 BEDROOMS, 2...	3 beds \| 2 baths \| 2,696 sq.ft.	$549,900	Airbnb cash on cash: 5.24% Traditional cash on cash: 2.37% Airbnb Rental Income: $4543 Traditional Rental Income: $2121 Airbnb ROI: 5.24% Traditional ROI: 2.37%
2933 HUDSON Street Baltimore , MD Welcome to 2933 Hudson Street, a three-story rowhome ideally located in the heart of highl...	2 beds \| 2 baths \| 1,120 sq.ft.	$239,900	Airbnb cash on cash: 7.68% Traditional cash on cash: 4.32% Airbnb Rental Income: $3230 Traditional Rental Income: $1741 Airbnb ROI: 7.68% Traditional ROI: 4.32%
606 Snow Goose Ln Annapolis , MD This home has it all. Gorgeous Brazilian hardwoods throughout! Gourmet kit w/top of the li...	4 beds \| 2 baths \| 2,004 sq.ft.	$565,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 2.11% Airbnb Rental Income: $3104 Traditional Rental Income: $2182 Airbnb ROI: 2.51% Traditional ROI: 2.11%
8514 Discovery Blvd WALKERSVILLE , MD USDA ELIGIBLE no down payment.This AMAZING opportunity to live just minutes from DOWNTOWN ...	3 beds \| 1 baths \| 1,500 sq.ft.	$299,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.07% Airbnb Rental Income: $2065 Traditional Rental Income: $1193 Airbnb ROI: 3.27% Traditional ROI: 2.07%
1745 Ridgely Rd Edgewater , MD Welcome home! This charming 2-bedroom, 1-bath single-family home is tucked away in a quiet...	2 beds \| 1 baths \| 800 sq.ft.	$327,500	Airbnb cash on cash: 3.17% Traditional cash on cash: 3.05% Airbnb Rental Income: $2284 Traditional Rental Income: $1679 Airbnb ROI: 3.17% Traditional ROI: 3.05%

Chicago, MD Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 0 Airbnb properties available for sale in Chicago.

In February 2026, the average Airbnb occupancy rate in Chicago is N/A%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chicago, MD

Other Airbnb Properties for Sale in Maryland

Baltimore , MD

4 beds | 3 baths | 1,571 sq.ft.

$480,000

Airbnb cash on cash: 5.4%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $4607

Traditional Rental Income: $2653

Airbnb ROI: 5.4%

Traditional ROI: 3.18%

Baltimore , MD

3 beds | 2 baths | 1,754 sq.ft.

$325,000

Airbnb cash on cash: 5.31%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $3328

Traditional Rental Income: $2120

Airbnb ROI: 5.31%

Traditional ROI: 3.79%

Silver Spring , MD

1 beds | 1 baths | 549 sq.ft.

$275,000

Airbnb cash on cash: 6.34%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $2892

Traditional Rental Income: $1610

Airbnb ROI: 6.34%

Traditional ROI: 3.99%

Silver Spring , MD

2 beds | 2 baths | 1,035 sq.ft.

$250,000

Airbnb cash on cash: 4.62%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $3070

Traditional Rental Income: $2118

Airbnb ROI: 4.62%

Traditional ROI: 3.55%

Silver Spring , MD

2 beds | 2 baths | 1,120 sq.ft.

$215,000

Airbnb cash on cash: 9.25%

Traditional cash on cash: 7.89%

Airbnb Rental Income: $3070

Traditional Rental Income: $2094

Airbnb ROI: 9.25%

Traditional ROI: 7.89%

Ocean City , MD

2 beds | 1 baths | 792 sq.ft.

$259,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 1.91%

Airbnb Rental Income: $1863

Traditional Rental Income: $1361

Airbnb ROI: 1.92%

Traditional ROI: 1.91%

Pasadena , MD

3 beds | 1 baths | 1,276 sq.ft.

$350,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 2.89%

Airbnb Rental Income: $3077

Traditional Rental Income: $1626

Airbnb ROI: 5.17%

Traditional ROI: 2.89%

Silver Spring , MD

3 beds | 2 baths | 1,550 sq.ft.

$350,000

Airbnb cash on cash: 6.77%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $3882

Traditional Rental Income: $2329

Airbnb ROI: 6.77%

Traditional ROI: 4.59%

Severna Park , MD

4 beds | 4 baths | 2,490 sq.ft.

$699,900

Airbnb cash on cash: 4.9%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $5672