Chesapeake Beach, Maryland Short-Term Rental Market
Chesapeake Beach, MD STRs averaged $211/night at 48.6% occupancy in April 2026, concentrated in maritime and commercial zones.
Quick Answer: Chesapeake Beach, Maryland is an active short-term rental market. average occupancy in the Maryland Area market area is 58%. average monthly revenue in the Maryland Area market area is $4,538. average daily rate in the Maryland Area market area is $290. the top operator in the Maryland Area market area is Evolve with 95 listings. market score is 59/100 (grade C).
Market data reflects the Maryland Area regional market, which includes Chesapeake Beach. Regulations, taxes, and permit details below are specific to Chesapeake Beach.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Chesapeake Beach is a small bayfront resort town of approximately 6,504 residents in Calvert County, Maryland, about 35 miles southeast of Washington, D.C. The town draws drive-market visitors from the D.C. and Baltimore metro areas for fishing, water park access, and Chesapeake Bay recreation. STR activity is legally concentrated in maritime and commercial zoning districts, as the town prohibits short-term rentals in residential zones under a 2019 housing ordinance.
The market posted a $210.85 average daily rate and 48.6% occupancy in April 2026, generating $102.42 in RevPAR. Year-over-year, occupancy declined 1.1%, ADR rose 1.3%, and revenue fell 0.3%, reflecting a broadly flat market trend. The 3,415 total listing records are distributed across bedroom sizes: 1-bedroom (1,272), 2-bedroom (686), 3-bedroom (748), 4-bedroom (397), and 5-bedroom or larger (308). By listing type, entire-place units dominate at 2,762, with private rooms at 643 and shared rooms at 10. Channel data shows 1,960 Airbnb-only listings, 1,233 on both platforms, and 222 VRBO-only. Market scores reflect balanced performance: investability 71.1, regulation 70.0, rental demand 69.5, seasonality 63.4, and revenue growth 62.9.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 40% |
| Feb | 49% |
| Mar | 51% |
| Apr | 53% |
| May | 56% |
| Jun | 61% |
| Jul | 63% |
| Aug | 61% |
| Sep | 53% |
| Oct | 51% |
| Nov | 46% |
| Dec | 45% |
Month-by-month nightly rates and revenue figures for Chesapeake Beach are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Maryland Area market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Maryland Area market as a whole, which includes Chesapeake Beach, so these counts are not Chesapeake Beach-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 95 | 2,986 | ★ 4.74 |
| 2 | Eastern Shore Vacations | 61 | 806 | ★ 4.76 |
| 3 | Flaneur | 34 | 981 | ★ 4.89 |
| 4 | Equitable | 28 | 286 | ★ 4.38 |
| 5 | Bartlett Real Estate Solutions | 16 | 1,109 | ★ 4.74 |
What Kind of STR Should I Buy in Chesapeake Beach?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Chesapeake Beach are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 57.4% |
| vrbo | 6.5% |
| both | 36.1% |
Home Value Trends (Chesapeake Beach)
Typical home values, median sale prices, and the 10-year price trend for Chesapeake Beach are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Chesapeake Beach — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Chesapeake Beach imposes one of the stricter local STR frameworks in Maryland. The town defines a rental as a housing unit leased for 30 consecutive days or more, making any stay under 30 days a short-term rental. Under the Zoning Ordinance and Housing Code Ordinance O-19-11 adopted in May 2019, STRs are prohibited in all residentially zoned districts. Short-term lodging is permitted only in maritime and commercial zoning districts, with an approved zoning permit required.
In residential areas, the only legal short-term lodging option is a Bed and Breakfast, defined as an owner-occupied or manager-occupied property providing lodging and meals by prearrangement. Operating a B&B requires a permit application, county inspection, full town and county permitting, and membership on the Maryland state B&B registry before any operations begin. Enforcement is strict: each day a violation continues is treated as a separate infraction subject to separate fines. On the tax side, Calvert County imposes a 5% accommodations tax on transient lodging charges, and Maryland’s 6% state sales and use tax also applies. As of 2025, Maryland requires booking platforms with 200 or more bookings or $100,000 or more in annual revenue to collect and remit hotel occupancy taxes to the state comptroller. No permit cost was confirmed in available sources for the zoning permit. Investors should treat residential Chesapeake Beach properties as STR-ineligible without a zoning reclassification.
Market Comparison
Chesapeake Beach’s 48.6% occupancy in April 2026 is below the US STR median of approximately 55%, and its $210.85 ADR is modestly below the US STR median of approximately $220. Both figures reflect the town’s small scale (6,504 residents) and the legal restriction of STR operations to commercial and maritime zones. RevPAR of $102.42 is modest by coastal mid-Atlantic standards. The 2025 annual average occupancy of 50.5% and ADR of $224 paint a somewhat stronger picture of full-year performance.
The professional management landscape is modest in scale relative to total listings. Evolve leads with 95 listings and 2,986 reviews (4.74 average rating). Eastern Shore Vacations follows with 61 listings and 806 reviews (4.76 rating). Flaneur holds 34 listings with a 4.89 average rating across 981 reviews. Equitable manages 28 listings with 286 reviews (4.38 rating), and Bartlett Real Estate Solutions rounds out the top five with 16 listings and 1,109 reviews (4.74 rating). The top five operators collectively manage 234 listings, representing approximately 6.9% of the 3,415 total listing records, a highly fragmented supply where independent operators hold dominant share.
Frequently Asked Questions About Chesapeake Beach, Maryland
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