Airbnb Properties for Sale in Chester, NY

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

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

Airbnb For Sale in Chester, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
Oxford Rd Chester, NY Oxford Rd, Blooming Grove, NY 10914 \| Other	N/A beds \| N/A baths \| N/A	$199,000	Airbnb cash on cash: 6.93% Traditional cash on cash: 3.24% Airbnb Rental Income: $2518 Traditional Rental Income: $1214 Airbnb ROI: 6.93% Traditional ROI: 3.24%
487 Black Meadow Rd Chester, NY Beautiful colonial farm house. Over 4,000 square feet. Large, foyer. Spacious living room ...	6 beds \| 3 baths \| 4,204 sq.ft.	$725,000	Airbnb cash on cash: 1.14% Traditional cash on cash: 0.37% Airbnb Rental Income: $3457 Traditional Rental Income: $2174 Airbnb ROI: 1.14% Traditional ROI: 0.37%
50 Elkay Dr Chester, NY 50 Elkay Dr, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$625,000	Airbnb cash on cash: 0.21% Traditional cash on cash: -0.89% Airbnb Rental Income: $2380 Traditional Rental Income: $1152 Airbnb ROI: 0.21% Traditional ROI: -0.89%
552 Pine Hill Rd Chester, NY 552 Pine Hill Rd, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 1.15% Airbnb Rental Income: $2380 Traditional Rental Income: $1176 Airbnb ROI: 3.34% Traditional ROI: 1.15%
492 Black Meadow Rd Chester, NY 492 Black Meadow Rd, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 0.43% Airbnb Rental Income: $2380 Traditional Rental Income: $1265 Airbnb ROI: 1.85% Traditional ROI: 0.43%
41 Bull Mine Rd Chester, NY 41 Bull Mine Rd, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$210,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 3.51% Airbnb Rental Income: $2380 Traditional Rental Income: $1327 Airbnb ROI: 5.85% Traditional ROI: 3.51%
Catherine Ct Chester, NY Catherine Ct, Chester, NY 10918 \| Other	N/A beds \| N/A baths \| N/A	$210,000	Airbnb cash on cash: 5.85% Traditional cash on cash: 2.24% Airbnb Rental Income: $2380 Traditional Rental Income: $1074 Airbnb ROI: 5.85% Traditional ROI: 2.24%

Vacation Rentals in Chester

There are 7 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $319,835 and the average price per square foot is $163. The cash on cash return on vacation rentals in Chester is 1.00%. The average monthly short term rental income in Chester is $3,457.

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

There are 7 Airbnb properties available for sale in Chester.

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

In June 2026, the average Airbnb occupancy rate in Chester is 23%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Chester, NY

Oxford Rd

Chester, NY

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

$199,000

Airbnb cash on cash: 6.93%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $2518

Traditional Rental Income: $1214

Airbnb ROI: 6.93%

Traditional ROI: 3.24%

487 Black Meadow Rd

Chester, NY

6 beds | 3 baths | 4,204 sq.ft.

$725,000

Airbnb cash on cash: 1.14%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $3457

Traditional Rental Income: $2174

Airbnb ROI: 1.14%

Traditional ROI: 0.37%

50 Elkay Dr

Chester, NY

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

$625,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: -0.89%

Airbnb Rental Income: $2380

Traditional Rental Income: $1152

Airbnb ROI: 0.21%

Traditional ROI: -0.89%

552 Pine Hill Rd

Chester, NY

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

$299,000

Airbnb cash on cash: 3.34%

Traditional cash on cash: 1.15%

Airbnb Rental Income: $2380

Traditional Rental Income: $1176

Airbnb ROI: 3.34%

Traditional ROI: 1.15%

492 Black Meadow Rd

Chester, NY

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

$399,000

Airbnb cash on cash: 1.85%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $2380

Traditional Rental Income: $1265

Airbnb ROI: 1.85%

Traditional ROI: 0.43%

41 Bull Mine Rd

Chester, NY

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

$210,000

Airbnb cash on cash: 5.85%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2380

Traditional Rental Income: $1327

Airbnb ROI: 5.85%

Traditional ROI: 3.51%

Catherine Ct

Chester, NY

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

$210,000

Airbnb cash on cash: 5.85%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $2380

Traditional Rental Income: $1074

Airbnb ROI: 5.85%

Traditional ROI: 2.24%

Vacation Rentals in Chester

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

How many Airbnb properties are available for sale in Chester?

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

What is the average Airbnb occupancy rate in Chester, NY?

How to get Chester, NY Airbnb data?

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