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Chesapeake City, Maryland short-term rental listings & supply

Updated By The AirDNA Data Team

Chesapeake City, Maryland has 195 active short-term rental listings, tracked across Airbnb, Vrbo, and Booking.com.

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Total active listings
195
+323.9% YoY
Most popular size
1BR
37.5% 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 195 active short-term rental listings as of August 2026, tracked across Airbnb, Vrbo, and Booking.com. Active supply is up 323.9% from August 2025 to August 2026. Here's how the market breaks down:

  • By property type: 89.2% entire homes, 10.8% private rooms.
  • By size: 37.5% 1-bedroom, 23.6% 2-bedroom, 19.9% 3-bedroom, 11.8% 5+ bedroom, and 7.1% 4-bedroom.
  • By channel: 50.8% Airbnb-only, 41.3% cross-listed and 8% Vrbo-only.
  • By availability: 69.3% full-time (271–365), 11.8% most of year (181–270), 9.5% seasonal (1–90 nights), and 9.5% part-time (91–180 nights).
  • By minimum stay: 54.4% 2 nights, 30.1% 30+ nights, 9.5% 3 nights, 3.7% 7–29 nights, 2% 4–6 nights, and 0.3% 1 night.
  • By cancellation policy: 38.2% moderate, 33.5% strict and 28.3% flexible.
63
Rental demand score
Full Chesapeake City market overview How Market Score is calculated
Analyst's take

Chesapeake City's Rental Demand score: 63 out of 100.

Chesapeake City's Rental Demand subscore is 63 out of 100, one of five inputs to its overall Market Score of 79.

Rental Demand combines two inputs: annual occupancy (48% in Chesapeake City) and year-over-year listing growth (active supply up 323.9% from August 2025 to August 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:

  1. 1Narrow to a neighborhoodNeighborhood metrics give a far more accurate picture of the exact area you're considering.
  2. 2Apply filtersFilter by bedrooms, price tier, amenities, and reviews to reach properties that actually match yours.
  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.

May '26Jul '26Aug '26Sep '26Sep '26Sep '26
See Chesapeake City's month-by-month supply trend in the AirDNA app.

Listing mix

Four ways to slice Chesapeake City's 195 listings

Property type

Entire home leads at 89.2%

  • Entire home89.2%
  • Private room10.8%

Bedrooms

1BR leads at 37.5%

  • 1BR37.5%
  • 2BR23.6%
  • 3BR19.9%
  • 4BR7.1%
  • 5BR+11.8%

Channel

Airbnb only leads at 50.8%

  • Airbnb only50.8%
  • Vrbo only8%
  • Multi-platform41.3%

Availability

Full-time (271–365) leads at 69.3%

  • Seasonal (1–90 nights)9.5%
  • Part-time (91–180 nights)9.5%
  • Most of year (181–270)11.8%
  • Full-time (271–365)69.3%

Listings by minimum stay

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

1 night
0.3%
2 nights
54.4%
3 nights
9.5%
4–6 nights
2%
7–29 nights
3.7%
30+ nights
30.1%

Listings by cancellation policy

Share of Chesapeake City active supply by host cancellation policy

Flexible
28.3%
Moderate
38.2%
Strict
33.5%

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: 195 listings, $47.7K average revenue, 48% occupancy, $321 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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