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Chesapeake City, Maryland short-term rental listings & supply

Updated By The AirDNA Data Team

Chesapeake City, Maryland has 47 active short-term rental listings, tracked across Airbnb, Vrbo, and Booking.com.

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Total active listings
47
+0.0% YoY
Most popular size
1BR
38.3% of all active listings
AirDNA tracks daily performance across 10M+ Airbnb, Vrbo, and Booking.com listings in 120K+ global markets. How we collect this data →10M+ listings across Airbnb, Vrbo & Booking.com in 120K+ markets. How we collect →

Chesapeake City, Maryland short-term rental listings

Chesapeake City has 47 active short-term rental listings as of July 2026, tracked across Airbnb, Vrbo, and Booking.com. Active supply is up 0.0% from July 2025 to July 2026. Here's how the market breaks down:

  • By property type: 89.4% entire homes, 10.6% private rooms.
  • By size: 38.3% 1-bedroom, 25.5% 2-bedroom, 17% 5+ bedroom, 12.8% 3-bedroom, and 6.4% 4-bedroom.
  • By channel: 57.4% Airbnb-only, 38.3% cross-listed and 4.3% Vrbo-only.
  • By availability: 74.5% full-time (271–365), 10.6% most of year (181–270), 8.5% seasonal (1–90 nights), and 6.4% part-time (91–180 nights).
  • By minimum stay: 59.6% 2 nights, 34% 30+ nights, 4.3% 7–29 nights, and 2.1% 3 nights.
  • By cancellation policy: 53.3% moderate, 40% flexible and 6.7% strict.
65
Rental demand score
Full Chesapeake City market overview How Market Score is calculated
Analyst's take

Chesapeake City's Rental Demand score: 65 out of 100.

Chesapeake City's Rental Demand subscore is 65 out of 100, one of five inputs to its overall Market Score of 75.

Rental Demand combines two inputs: annual occupancy (39% in Chesapeake City) and year-over-year listing growth (active supply up 0.0% from July 2025 to July 2026).

It is benchmarked against other short-term rental markets in the same country with at least 15 active listings.

The Market Score is a starting point, not an investment decision.

Market-level averages hide wide variation. Here's how to go deeper in the app:

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  3. 3Estimate one addressProject what one specific property can earn with a custom comp set built from its exact specs.
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Key definitions

How AirDNA defines these metrics

Active listings
Active listings are the short-term rentals on Airbnb, Vrbo, and Booking.com that were available or booked in the trailing 12 months. AirDNA de-duplicates the same home across channels, and the count refreshes monthly.How AirDNA counts active listings →
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Active listings over timeIllustrative preview

How Chesapeake City's active short-term rental supply has trended over the past year.

Oct '25Dec '25Feb '26Apr '26Jun '26Aug '26
See Chesapeake City's month-by-month supply trend in the AirDNA app.

Listing mix

Four ways to slice Chesapeake City's 47 listings

Property type

Entire home leads at 89.4%

  • Entire home89.4%
  • Private room10.6%

Bedrooms

1BR leads at 38.3%

  • 1BR38.3%
  • 2BR25.5%
  • 3BR12.8%
  • 4BR6.4%
  • 5BR+17%

Channel

Airbnb only leads at 57.4%

  • Airbnb only57.4%
  • Vrbo only4.3%
  • Multi-platform38.3%

Availability

Full-time (271–365) leads at 74.5%

  • Seasonal (1–90 nights)8.5%
  • Part-time (91–180 nights)6.4%
  • Most of year (181–270)10.6%
  • Full-time (271–365)74.5%

Listings by minimum stay

Share of Chesapeake City active supply by host-set minimum stay

2 nights
59.6%
3 nights
2.1%
7–29 nights
4.3%
30+ nights
34%

Listings by cancellation policy

Share of Chesapeake City active supply by host cancellation policy

Flexible
40%
Moderate
53.3%
Strict
6.7%

This is the tip of the iceberg

Go deeper on Chesapeake City supply in the app.

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Explore more Chesapeake City data

Keep digging into Chesapeake City

Chesapeake City market overview

The full Chesapeake City market: 47 listings, $34.3K average revenue, 39% occupancy, $471 ADR. Topline metrics and the AirDNA Market Score.

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Revenue

Annual earnings, revenue by property type, and daily rates by segment.

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Seasonality

Occupancy, RevPAR, peak and trough months, seasonality score.

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Property Managers

The largest property managers operating in Chesapeake City.

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Explore more markets

Other short-term rental markets in Maryland

Frequently asked

Common questions about Chesapeake City

Get more in the app

There's a lot more inside the AirDNA app.

  • Custom comp sets
  • Neighborhood data
  • Deep filters
  • Heat maps
  • For Sale by yield
  • Export the data
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