Airbnb Properties for Sale in Chesapeake, VA

Looking for a vacation rental investment in Chesapeake, VA with high ROI ?

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

Airbnb For Sale in Chesapeake, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4227 Meander Way Chesapeake, VA THIS HOME IS LIKE NEW BUILT IN 2023 4 BEDROOM, 3.5 BATH, UPGRADED LIGHTING, CABINETS, APPL...	4 beds \| 4 baths \| 2,034 sq.ft.	$395,000	Airbnb cash on cash: 9.33% Traditional cash on cash: 4.77% Airbnb Rental Income: $5351 Traditional Rental Income: $2581 Airbnb ROI: 9.33% Traditional ROI: 4.77%
1530 Jolliff Road Chesapeake, VA Start building your custom dream home today! Exceptional new construction opportunity on a...	4 beds \| 3 baths \| 2,000 sq.ft.	$599,900	Airbnb cash on cash: 5.47% Traditional cash on cash: 2.95% Airbnb Rental Income: $5351 Traditional Rental Income: $2860 Airbnb ROI: 5.47% Traditional ROI: 2.95%
2156 Seastone Trace Chesapeake, VA Welcome to the peaceful neighborhood of Waterstone. Access to WB Park directly accross the...	4 beds \| 3 baths \| 2,860 sq.ft.	$554,900	Airbnb cash on cash: 6.07% Traditional cash on cash: 3.46% Airbnb Rental Income: $5351 Traditional Rental Income: $2918 Airbnb ROI: 6.07% Traditional ROI: 3.46%
Airbnb Properties for Sale in Other Cities of Virginia
1322 Porter Street Richmond , VA Charming Manchester Bungalow with Outdoor Living & City Access. Step into comfort while en...	3 beds \| 1 baths \| 1,308 sq.ft.	$214,950	Airbnb cash on cash: 7.34% Traditional cash on cash: 5.86% Airbnb Rental Income: $2655 Traditional Rental Income: $1722 Airbnb ROI: 7.34% Traditional ROI: 5.86%
3874 Main St CHINCOTEAGUE ISLAND , VA Well-maintained 1925 historic home on Main Street in the heart of Chincoteague, within sho...	3 beds \| 1 baths \| 1,652 sq.ft.	$498,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 1.66% Airbnb Rental Income: $2610 Traditional Rental Income: $1710 Airbnb ROI: 2.25% Traditional ROI: 1.66%
270 Bogey Dr Abingdon , VA Welcome to this gorgeously remodeled 4-bedroom, 3-bathroom home located in one of Abingdon...	4 beds \| 2 baths \| 1,984 sq.ft.	$429,000	Airbnb cash on cash: 4.72% Traditional cash on cash: 4.18% Airbnb Rental Income: $3245 Traditional Rental Income: $2301 Airbnb ROI: 4.72% Traditional ROI: 4.18%
1101 Starling Dr Richmond , VA Beautiful brick Rancher available in Tuckahoe! Located in the desirable Greenbrier Hills n...	3 beds \| 1 baths \| 1,088 sq.ft.	$340,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 3.4% Airbnb Rental Income: $4097 Traditional Rental Income: $1769 Airbnb ROI: 7.96% Traditional ROI: 3.4%
4609 W Grace Street Richmond , VA Welcome to 4609 W. Grace Street! This spacious brick-and-slate cape sits on a rare double ...	3 beds \| 3 baths \| 2,470 sq.ft.	$735,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.82% Airbnb Rental Income: $3665 Traditional Rental Income: $2803 Airbnb ROI: 1.91% Traditional ROI: 1.82%
8807 Midway Road Richmond , VA Wonderfully updated ranch situated in sought after location of the west end! Close to rest...	3 beds \| 2 baths \| 1,167 sq.ft.	$355,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 3.81% Airbnb Rental Income: $4097 Traditional Rental Income: $1959 Airbnb ROI: 7.61% Traditional ROI: 3.81%
956 Maiden St Abingdon , VA Condo/Townhouse - Convenient living in Abingdon, VA and Move-in Ready Welcome to Unit ...	2 beds \| 2 baths \| 1,150 sq.ft.	$189,900	Airbnb cash on cash: 7.73% Traditional cash on cash: 6.17% Airbnb Rental Income: $2395 Traditional Rental Income: $1512 Airbnb ROI: 7.73% Traditional ROI: 6.17%
226 Hallock Dr Abingdon , VA This move-in ready home offers comfort and convenience in a great location close to shoppi...	3 beds \| 2 baths \| 1,109 sq.ft.	$210,000	Airbnb cash on cash: 9.62% Traditional cash on cash: 5.99% Airbnb Rental Income: $2965 Traditional Rental Income: $1559 Airbnb ROI: 9.62% Traditional ROI: 5.99%
6058 Old Telegraph Rd Alexandria , VA Priced below assessment! Privacy abounds off the beaten path! Mid-century all-brick ramble...	3 beds \| 3 baths \| 1,520 sq.ft.	$897,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 1.21% Airbnb Rental Income: $5328 Traditional Rental Income: $2600 Airbnb ROI: 3.19% Traditional ROI: 1.21%
705 Keppel Dr Newport News , VA What a house! Hardwood floors throughout! Kitchen has been remodeled recently. Updated ...	4 beds \| 2 baths \| 1,700 sq.ft.	$260,000	Airbnb cash on cash: 9.41% Traditional cash on cash: 4.43% Airbnb Rental Income: $3682 Traditional Rental Income: $1657 Airbnb ROI: 9.41% Traditional ROI: 4.43%
3633 Britt Terrace Virginia Beach , VA Recently renovated and remodeled. This move-in-ready split-level home offers three living ...	4 beds \| 3 baths \| 1,612 sq.ft.	$599,000	Airbnb cash on cash: 3.87% Traditional cash on cash: 3.05% Airbnb Rental Income: $3988 Traditional Rental Income: $2679 Airbnb ROI: 3.87% Traditional ROI: 3.05%
6809 SOUTH Drive Richmond , VA Welcome to your private oasis near the James River, where space, serenity, and nature meet...	4 beds \| 2 baths \| 2,612 sq.ft.	$699,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 2.09% Airbnb Rental Income: $3558 Traditional Rental Income: $2719 Airbnb ROI: 2.18% Traditional ROI: 2.09%
240 Huntstree Pl Newport News , VA Beautiful home in the sought after Summerlake community in Newport News. This home boast m...	4 beds \| 2 baths \| 2,079 sq.ft.	$330,000	Airbnb cash on cash: 6.46% Traditional cash on cash: 5.62% Airbnb Rental Income: $3682 Traditional Rental Income: $2617 Airbnb ROI: 6.46% Traditional ROI: 5.62%
7753 Patriot Dr #51 ANNANDALE , VA Spacious and rarely available top-level end-unit condo featuring 3 bedrooms and 2 full bat...	3 beds \| 2 baths \| 1,132 sq.ft.	$295,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 4.2% Airbnb Rental Income: $3951 Traditional Rental Income: $2820 Airbnb ROI: 5.22% Traditional ROI: 4.2%
3749 Willow St CHINCOTEAGUE ISLAND , VA Turn Key Chincoteague Island Retreat with many stylish updates! This beautifully refreshed...	3 beds \| 1 baths \| 978 sq.ft.	$315,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 4.31% Airbnb Rental Income: $2610 Traditional Rental Income: $1710 Airbnb ROI: 5.24% Traditional ROI: 4.31%

Vacation Rentals in Chesapeake

There are 3 vacation rental properties available for sale in the city of Chesapeake . The median list price of Airbnb properties available for sale in Chesapeake is $439,000 and the average price per square foot is $208. The cash on cash return on vacation rentals in Chesapeake is N/A%. The average monthly short term rental income in Chesapeake is $1,001.

Chesapeake, VA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 3 Airbnb properties available for sale in Chesapeake.

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

In February 2026, the average Airbnb occupancy rate in Chesapeake is 19%.

In 2026, the highest Airbnb occupancy rate in Chesapeake are in Greenbrier West (21%), South Norfolk (22%) and South Norfolk (28%).

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

Your search for investment property begins and ends here

Airbnb For Sale in Chesapeake, VA

4227 Meander Way

Chesapeake, VA

4 beds | 4 baths | 2,034 sq.ft.

$395,000

Airbnb cash on cash: 9.33%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $5351

Traditional Rental Income: $2581

Airbnb ROI: 9.33%

Traditional ROI: 4.77%

1530 Jolliff Road

Chesapeake, VA

4 beds | 3 baths | 2,000 sq.ft.

$599,900

Airbnb cash on cash: 5.47%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $5351

Traditional Rental Income: $2860

Airbnb ROI: 5.47%

Traditional ROI: 2.95%

2156 Seastone Trace

Chesapeake, VA

4 beds | 3 baths | 2,860 sq.ft.

$554,900

Airbnb cash on cash: 6.07%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $5351

Traditional Rental Income: $2918

Airbnb ROI: 6.07%

Traditional ROI: 3.46%

Airbnb Properties for Sale in Other Cities of Virginia

Richmond , VA

3 beds | 1 baths | 1,308 sq.ft.

$214,950

Airbnb cash on cash: 7.34%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $2655

Traditional Rental Income: $1722

Airbnb ROI: 7.34%

Traditional ROI: 5.86%

CHINCOTEAGUE ISLAND , VA

3 beds | 1 baths | 1,652 sq.ft.

$498,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $2610

Traditional Rental Income: $1710

Airbnb ROI: 2.25%

Traditional ROI: 1.66%

Abingdon , VA

4 beds | 2 baths | 1,984 sq.ft.

$429,000

Airbnb cash on cash: 4.72%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $3245

Traditional Rental Income: $2301

Airbnb ROI: 4.72%

Traditional ROI: 4.18%

Richmond , VA

3 beds | 1 baths | 1,088 sq.ft.

$340,000

Airbnb cash on cash: 7.96%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $4097

Traditional Rental Income: $1769

Airbnb ROI: 7.96%

Traditional ROI: 3.4%

Richmond , VA

3 beds | 3 baths | 2,470 sq.ft.

$735,000

Airbnb cash on cash: 1.91%

Traditional cash on cash: 1.82%

Airbnb Rental Income: $3665

Traditional Rental Income: $2803

Airbnb ROI: 1.91%

Traditional ROI: 1.82%

Richmond , VA

3 beds | 2 baths | 1,167 sq.ft.

$355,000