Airbnb Properties for Sale in Chestertown, MD

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

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

Airbnb For Sale in Chestertown, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
0 Round Top Rd CHESTERTOWN, MD 0 Round Top Rd, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 0.82% Airbnb Rental Income: $1882 Traditional Rental Income: $643 Airbnb ROI: 4.7% Traditional ROI: 0.82%
109 2nd St CHESTERTOWN, MD 109 2nd St, CHESTERTOWN, MD 21620 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 3.18% Airbnb Rental Income: $1882 Traditional Rental Income: $774 Airbnb ROI: 7.85% Traditional ROI: 3.18%
1904 Pondtown Rd CHESTERTOWN, MD 1904 Pondtown Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,967 sq.ft.	$265,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.53% Airbnb Rental Income: $2448 Traditional Rental Income: $1496 Airbnb ROI: 4.95% Traditional ROI: 3.53%
517 Round Top Rd CHESTERTOWN, MD 517 Round Top Rd, CHESTERTOWN, MD 21620 \| Single Family Residential	3 beds \| 1 baths \| 1,248 sq.ft.	$349,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 2.9% Airbnb Rental Income: $2448 Traditional Rental Income: $1730 Airbnb ROI: 3.27% Traditional ROI: 2.9%

Vacation Rentals in Chestertown

There are 5 vacation rental properties available for sale in the city of Chestertown . The median list price of Airbnb properties available for sale in Chestertown is $454,765 and the average price per square foot is $216. The cash on cash return on vacation rentals in Chestertown is 2.00%. The average monthly short term rental income in Chestertown is $2,288.

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

There are 5 Airbnb properties available for sale in Chestertown.

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

In June 2026, the average Airbnb occupancy rate in Chestertown is 25%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chestertown, MD

0 Round Top Rd

CHESTERTOWN, MD

N/A beds | N/A baths | N/A

$200,000

Airbnb cash on cash: 4.7%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $1882

Traditional Rental Income: $643

Airbnb ROI: 4.7%

Traditional ROI: 0.82%

109 2nd St

CHESTERTOWN, MD

N/A beds | N/A baths | N/A

$135,000

Airbnb cash on cash: 7.85%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $1882

Traditional Rental Income: $774

Airbnb ROI: 7.85%

Traditional ROI: 3.18%

1904 Pondtown Rd

CHESTERTOWN, MD

3 beds | 1 baths | 1,967 sq.ft.

$265,000

Airbnb cash on cash: 4.95%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2448

Traditional Rental Income: $1496

Airbnb ROI: 4.95%

Traditional ROI: 3.53%

517 Round Top Rd

CHESTERTOWN, MD

3 beds | 1 baths | 1,248 sq.ft.

$349,900

Airbnb cash on cash: 3.27%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $2448

Traditional Rental Income: $1730

Airbnb ROI: 3.27%

Traditional ROI: 2.9%

Vacation Rentals in Chestertown

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

How many Airbnb properties are available for sale in Chestertown?

Which neighborhoods in Chestertown to invest in 2026 for short term rentals?

What is the average Airbnb occupancy rate in Chestertown, MD?

How to get Chestertown, MD Airbnb data?

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