Airbnb Properties for Sale in Chester, MD

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

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

Airbnb For Sale in Chester, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1509 CALVERT RD CHESTER, MD Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. F...	4 beds \| 3 baths \| N/A	$1,350,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.06% Airbnb Rental Income: $4254 Traditional Rental Income: $3214 Airbnb ROI: 1.17% Traditional ROI: 1.06%
107 LEE Road CHESTER, MD 107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backya...	3 beds \| 1 baths \| 960 sq.ft.	$305,000	Airbnb cash on cash: 6.37% Traditional cash on cash: 4.85% Airbnb Rental Income: $3121 Traditional Rental Income: $1974 Airbnb ROI: 6.37% Traditional ROI: 4.85%
54F QUEEN CAROLINE CT CHESTER, MD Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters...	3 beds \| 3 baths \| N/A	$349,900	Airbnb cash on cash: 3.53% Traditional cash on cash: 2.29% Airbnb Rental Income: $3121 Traditional Rental Income: $2006 Airbnb ROI: 3.53% Traditional ROI: 2.29%
134 RICHARD INGLE Way CHESTER, MD Experience the best of Kent Island living in this beautifully maintained coastal home, ide...	4 beds \| 4 baths \| 2,185 sq.ft.	$739,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 2.45% Airbnb Rental Income: $4254 Traditional Rental Income: $3344 Airbnb ROI: 2.46% Traditional ROI: 2.45%
315 BENTONS PLEASURE Road CHESTER, MD REDUCED!!! This 3 bedroom 2 full bath brick rancher is located 1.88 for plenty of privacy ...	3 beds \| 2 baths \| 1,688 sq.ft.	$599,900	Airbnb cash on cash: 2.54% Traditional cash on cash: 2.1% Airbnb Rental Income: $3121 Traditional Rental Income: $2161 Airbnb ROI: 2.54% Traditional ROI: 2.1%
1717 HARBOR Drive CHESTER, MD Discover exceptional waterfront living on picturesque Cox Creek. Beautifully renovated app...	3 beds \| 3 baths \| 2,742 sq.ft.	$1,199,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 0.26% Airbnb Rental Income: $3121 Traditional Rental Income: $2235 Airbnb ROI: 0.42% Traditional ROI: 0.26%
205 DOMINION Lane CHESTER, MD Opportunity on Kent Island! Welcome to 205 Dominion Lane in Chester, a detached home situa...	3 beds \| 2 baths \| 1,160 sq.ft.	$300,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 6.11% Airbnb Rental Income: $3121 Traditional Rental Income: $2321 Airbnb ROI: 6.44% Traditional ROI: 6.11%
2627 CECIL DR CHESTER, MD Harbor View - This beautiful waterfront home has been completely remodeled in 2026, new si...	3 beds \| 2 baths \| N/A	$699,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.36% Airbnb Rental Income: $3121 Traditional Rental Income: $2340 Airbnb ROI: 1.47% Traditional ROI: 1.36%

Vacation Rentals in Chester

There are 8 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $567,230 and the average price per square foot is $309. The cash on cash return on vacation rentals in Chester is 1.00%. The average monthly short term rental income in Chester is $3,121.

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

There are 8 Airbnb properties available for sale in Chester.

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

In November 2026, the average Airbnb occupancy rate in Chester is 25%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chester, MD

1509 CALVERT RD

CHESTER, MD

4 beds | 3 baths | N/A

$1,350,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4254

Traditional Rental Income: $3214

Airbnb ROI: 1.17%

Traditional ROI: 1.06%

107 LEE Road

CHESTER, MD

3 beds | 1 baths | 960 sq.ft.

$305,000

Airbnb cash on cash: 6.37%

Traditional cash on cash: 4.85%

Airbnb Rental Income: $3121

Traditional Rental Income: $1974

Airbnb ROI: 6.37%

Traditional ROI: 4.85%

54F QUEEN CAROLINE CT

CHESTER, MD

3 beds | 3 baths | N/A

$349,900

Airbnb cash on cash: 3.53%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $3121

Traditional Rental Income: $2006

Airbnb ROI: 3.53%

Traditional ROI: 2.29%

134 RICHARD INGLE Way

CHESTER, MD

4 beds | 4 baths | 2,185 sq.ft.

$739,000

Airbnb cash on cash: 2.46%

Traditional cash on cash: 2.45%

Airbnb Rental Income: $4254

Traditional Rental Income: $3344

Airbnb ROI: 2.46%

Traditional ROI: 2.45%

315 BENTONS PLEASURE Road

CHESTER, MD

3 beds | 2 baths | 1,688 sq.ft.

$599,900

Airbnb cash on cash: 2.54%

Traditional cash on cash: 2.1%

Airbnb Rental Income: $3121

Traditional Rental Income: $2161

Airbnb ROI: 2.54%

Traditional ROI: 2.1%

1717 HARBOR Drive

CHESTER, MD

3 beds | 3 baths | 2,742 sq.ft.

$1,199,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $3121

Traditional Rental Income: $2235

Airbnb ROI: 0.42%

Traditional ROI: 0.26%

205 DOMINION Lane

CHESTER, MD

3 beds | 2 baths | 1,160 sq.ft.

$300,000

Airbnb cash on cash: 6.44%

Traditional cash on cash: 6.11%

Airbnb Rental Income: $3121

Traditional Rental Income: $2321

Airbnb ROI: 6.44%

Traditional ROI: 6.11%

2627 CECIL DR

CHESTER, MD

3 beds | 2 baths | N/A

$699,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $3121

Traditional Rental Income: $2340

Airbnb ROI: 1.47%