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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
241 Meadow Avenue Chester, NY Discover the timeless charm and endless potential of this classic Colonial farmhouse, idea...	4 beds \| 2 baths \| 1,560 sq.ft.	$349,999	Airbnb cash on cash: 8.33% Traditional cash on cash: 4.72% Airbnb Rental Income: $5004 Traditional Rental Income: $2796 Airbnb ROI: 8.33% Traditional ROI: 4.72%
504 Bull Mill Road Chester, NY A NEW HOME IS A NEW BEGINNING!! Impressive home - redone to perfection is waiting for you!...	4 beds \| 3 baths \| 2,777 sq.ft.	$945,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 1.6% Airbnb Rental Income: $5004 Traditional Rental Income: $3905 Airbnb ROI: 1.68% Traditional ROI: 1.6%
2113 Whispering Hills Chester, NY Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a...	2 beds \| 1 baths \| 1,084 sq.ft.	$275,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.12% Airbnb Rental Income: $2930 Traditional Rental Income: $1992 Airbnb ROI: 3.12% Traditional ROI: 2.12%
90 Pewter Circle Chester, NY This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf ar...	4 beds \| 3 baths \| 2,250 sq.ft.	$759,900	Airbnb cash on cash: 3.4% Traditional cash on cash: 3.04% Airbnb Rental Income: $5004 Traditional Rental Income: $3727 Airbnb ROI: 3.4% Traditional ROI: 3.04%
60 Whitetail Run Chester, NY Beautifully maintained Colonial set on a picturesque and private property offering the per...	4 beds \| 3 baths \| 2,588 sq.ft.	$900,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.21% Airbnb Rental Income: $5004 Traditional Rental Income: $3637 Airbnb ROI: 1.62% Traditional ROI: 1.21%
206 Greycourt Road Chester, NY INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 20...	N/A beds \| N/A baths \| 960 sq.ft.	$999,900	Airbnb cash on cash: 1.99% Traditional cash on cash: -0.98% Airbnb Rental Income: $5004 Traditional Rental Income: $1220 Airbnb ROI: 1.99% Traditional ROI: -0.98%
19 Bull Mine Road Chester, NY Set on 2.3 acres in Chester, this impressive property offers space, versatility, and sceni...	4 beds \| 3 baths \| 3,332 sq.ft.	$949,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.79% Airbnb Rental Income: $5004 Traditional Rental Income: $3558 Airbnb ROI: 1.27% Traditional ROI: 0.79%
185 Oxford Road Chester, NY Welcome to 185 Oxford Road, Chester! This charming 3-bedroom Ranch home is now available f...	3 beds \| 1 baths \| 1,062 sq.ft.	$389,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.94% Airbnb Rental Income: $2963 Traditional Rental Income: $2231 Airbnb ROI: 3.08% Traditional ROI: 2.94%
1168 Craigville Road Chester, NY MOTIVATED SELLER PRIVATE WOODED COLONIAL!! 4 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Ea...	4 beds \| 3 baths \| 2,616 sq.ft.	$765,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 1.25% Airbnb Rental Income: $5004 Traditional Rental Income: $3241 Airbnb ROI: 2.29% Traditional ROI: 1.25%
1 Sanford Avenue Chester, NY Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering ov...	4 beds \| 3 baths \| 2,280 sq.ft.	$725,000	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.72% Airbnb Rental Income: $5004 Traditional Rental Income: $3789 Airbnb ROI: 3.01% Traditional ROI: 2.72%
20 Mountainside Drive Chester, NY 20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on ...	4 beds \| 4 baths \| 3,080 sq.ft.	$739,900	Airbnb cash on cash: 2.44% Traditional cash on cash: 1.75% Airbnb Rental Income: $5004 Traditional Rental Income: $3505 Airbnb ROI: 2.44% Traditional ROI: 1.75%
13 Bianca Boulevard Chester, NY Gracious Colonial home features the best of the traditional style with the appeal of a con...	4 beds \| 3 baths \| 3,296 sq.ft.	$690,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 1.68% Airbnb Rental Income: $5004 Traditional Rental Income: $3238 Airbnb ROI: 2.84% Traditional ROI: 1.68%
3 Garnett Hill Road Chester, NY This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansi...	4 beds \| 3 baths \| 2,516 sq.ft.	$789,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 0.8% Airbnb Rental Income: $5004 Traditional Rental Income: $3192 Airbnb ROI: 1.87% Traditional ROI: 0.8%
1212 Whispering Hills Chester, NY Welcome to stress-free Hudson Valley living in the desirable Whispering Hills community! T...	2 beds \| 1 baths \| 1,084 sq.ft.	$269,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 1.68% Airbnb Rental Income: $2930 Traditional Rental Income: $1866 Airbnb ROI: 3.21% Traditional ROI: 1.68%
3706 Whispering Hills Chester, NY Discover a compelling combination of space, convenience and Chester accessibility at 3706 ...	2 beds \| 2 baths \| 1,086 sq.ft.	$339,900	Airbnb cash on cash: 3.65% Traditional cash on cash: 2.44% Airbnb Rental Income: $2930 Traditional Rental Income: $1868 Airbnb ROI: 3.65% Traditional ROI: 2.44%
28 Pewter Circle Chester, NY Discover a lovingly maintained 4-bedroom Colonial home for sale in Chester, NY, in the War...	4 beds \| 3 baths \| 3,763 sq.ft.	$719,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 1.39% Airbnb Rental Income: $5004 Traditional Rental Income: $3268 Airbnb ROI: 2.45% Traditional ROI: 1.39%
34 Boville Court Chester, NY Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a...	4 beds \| 4 baths \| 2,707 sq.ft.	$839,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 1.36% Airbnb Rental Income: $5004 Traditional Rental Income: $3520 Airbnb ROI: 1.95% Traditional ROI: 1.36%
166 Bull Mill Road Chester, NY Looking for the perfect weekend stay, peaceful getaway, or a one-of-a-kind place to call h...	2 beds \| 1 baths \| 1,004 sq.ft.	$289,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 2.9% Airbnb Rental Income: $2930 Traditional Rental Income: $1982 Airbnb ROI: 3.89% Traditional ROI: 2.9%
7 Hambletonian Avenue Chester, NY Great new price! Come take a look at this 2 bedroom charmer with additional room offers po...	2 beds \| 1 baths \| 1,026 sq.ft.	$379,900	Airbnb cash on cash: 2.99% Traditional cash on cash: 2.4% Airbnb Rental Income: $2930 Traditional Rental Income: $2043 Airbnb ROI: 2.99% Traditional ROI: 2.4%
63 Hubshop Road Chester, NY Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3...	4 beds \| 3 baths \| 2,060 sq.ft.	$459,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 4.66% Airbnb Rental Income: $5004 Traditional Rental Income: $3669 Airbnb ROI: 5.38% Traditional ROI: 4.66%
8 Bridle Lane Chester, NY Welcome to 8 Bridle Lane, Chester, NY, located in the desirable Surrey Meadows neighborhoo...	4 beds \| 2 baths \| 1,820 sq.ft.	$495,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 4.04% Airbnb Rental Income: $5004 Traditional Rental Income: $3382 Airbnb ROI: 5.34% Traditional ROI: 4.04%

Vacation Rentals in Chester

There are 21 vacation rental properties available for sale in the city of Chester . The median list price of Airbnb properties available for sale in Chester is $384,817 and the average price per square foot is $217. The cash on cash return on vacation rentals in Chester is 2.00%. The average monthly short term rental income in Chester is $3,960.

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

There are 21 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 30%.

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

241 Meadow Avenue

Chester, NY

4 beds | 2 baths | 1,560 sq.ft.

$349,999

Airbnb cash on cash: 8.33%

Traditional cash on cash: 4.72%

Airbnb Rental Income: $5004

Traditional Rental Income: $2796

Airbnb ROI: 8.33%

Traditional ROI: 4.72%

504 Bull Mill Road

Chester, NY

4 beds | 3 baths | 2,777 sq.ft.

$945,000

Airbnb cash on cash: 1.68%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $5004

Traditional Rental Income: $3905

Airbnb ROI: 1.68%

Traditional ROI: 1.6%

2113 Whispering Hills

Chester, NY

2 beds | 1 baths | 1,084 sq.ft.

$275,000

Airbnb cash on cash: 3.12%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $2930

Traditional Rental Income: $1992

Airbnb ROI: 3.12%

Traditional ROI: 2.12%

90 Pewter Circle

Chester, NY

4 beds | 3 baths | 2,250 sq.ft.

$759,900

Airbnb cash on cash: 3.4%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $5004

Traditional Rental Income: $3727

Airbnb ROI: 3.4%

Traditional ROI: 3.04%

60 Whitetail Run

Chester, NY

4 beds | 3 baths | 2,588 sq.ft.

$900,000

Airbnb cash on cash: 1.62%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $5004

Traditional Rental Income: $3637

Airbnb ROI: 1.62%

Traditional ROI: 1.21%

206 Greycourt Road

Chester, NY

N/A beds | N/A baths | 960 sq.ft.

$999,900

Airbnb cash on cash: 1.99%

Traditional cash on cash: -0.98%

Airbnb Rental Income: $5004

Traditional Rental Income: $1220

Airbnb ROI: 1.99%

Traditional ROI: -0.98%

19 Bull Mine Road

Chester, NY

4 beds | 3 baths | 3,332 sq.ft.

$949,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 0.79%

Airbnb Rental Income: $5004

Traditional Rental Income: $3558

Airbnb ROI: 1.27%

Traditional ROI: 0.79%

185 Oxford Road

Chester, NY

3 beds | 1 baths | 1,062 sq.ft.

$389,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $2963

Traditional Rental Income: $2231

Airbnb ROI: 3.08%