Chesapeake, Virginia Short-Term Rental Market
Chesapeake, VA STRs averaged $222/night at 56.0% occupancy in May 2026 across a market dominated by entire-place listings.
Quick Answer: Chesapeake, Virginia is an active short-term rental market. average occupancy is 73%. average monthly revenue is $7,033. average daily rate is $388. the top operator is Village Realty with 351 listings. market score is 55/100 (grade D).
Market data reflects the Norfolk/VA Beach regional market, which includes Chesapeake. Regulations, taxes, and permit details below are specific to Chesapeake.
Market Score Breakdown
Five dimensions Apivex evaluates per market.
Market Overview
Chesapeake, Virginia sits within the Hampton Roads metro, offering STR operators access to a large regional leisure market anchored by outdoor recreation on the Atlantic Intracoastal Waterway, the Great Dismal Swamp, and proximity to Virginia Beach and Norfolk. The market logged a $221.82 average daily rate and 56.0% occupancy in May 2026, producing $124.31 in revenue per available room. Year-over-year, ADR rose 5.9% while occupancy declined 6.5%, resulting in a net revenue increase of 4.1% versus the prior May. The city’s population of approximately 256,610 generates a steady base of drive-market and military-connected demand.
Listing supply is substantial and diversified. The market carries 9,543 active listing records across bedroom tiers: 1-bedroom (2,363 listings), 2-bedroom (2,371), 3-bedroom (1,645), 4-bedroom (1,347), and 5-bedroom or larger (1,802). By listing type, entire-place units account for 8,632 of the total, with private rooms at 910 and shared rooms at just 1, confirming the market is overwhelmingly oriented toward whole-property stays. Channel distribution shows 4,201 listings on both Airbnb and VRBO, 3,763 Airbnb-only, and 1,579 VRBO-only. Market scores from the dimension snapshot show strong investability (69.3) and exceptional revenue growth (98.3 out of 100), partially offset by moderate rental demand (49.6) and a seasonality score of 45.8 reflecting meaningful shoulder-season softness.
Seasonal Patterns
| Month | Occupancy | ADR | Revenue |
|---|---|---|---|
| Jan | 39% | $145 | $1,720 |
| Feb | 52% | $145 | $1,759 |
| Mar | 58% | $164 | $2,277 |
| Apr | 57% | $194 | $2,705 |
| May | 59% | $246 | $3,391 |
| Jun | 71% | $335 | $5,724 |
| Jul | 72% | $324 | $5,883 |
| Aug | 71% | $315 | $5,657 |
| Sep | 51% | $232 | $3,154 |
| Oct | 46% | $184 | $2,311 |
| Nov | 46% | $172 | $2,024 |
| Dec | 44% | $166 | $2,024 |
Top Short-Term Rental Operators in Chesapeake
Ranked by total active listings. Useful for understanding the competitive landscape.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Village Realty | 351 | 1,976 | ★ 4.38 |
| 2 | Vacasa | 277 | 8,440 | ★ 4.29 |
| 3 | Sojourn | 262 | 3,757 | ★ 4.53 |
| 4 | Brindley Beach Vacation & Sales | 234 | 619 | ★ 4.11 |
| 5 | Christian Taylor Vacations | 200 | 1,552 | ★ 4.57 |
What Kind of STR Should I Buy in Chesapeake?
Revenue and pricing by property type, tier, and bedroom count.
Revenue by Bedroom Count
| 1 bed | 2,363 |
| 2 bed | 2,371 |
| 3 bed | 1,645 |
| 4 bed | 1,347 |
| 5 bed | 1,802 |
ADR by Property Tier
| Entire Home | $417 |
| Luxury | $696 |
| Professionally Managed | $504 |
Revenue by Dwelling Type
| Apartment | $4,697 |
| Entire Place | $7,516 |
| House | $8,503 |
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 39.4% |
| vrbo | 16.5% |
| both | 44% |
Investment Analysis
Chesapeake’s investment case rests on a spread between average-tier and professionally managed performance. The overall market ADR in May 2026 was $221.82, while entire-home listings averaged $243.42 and professionally managed properties averaged $278.39 per night, a 25.5% premium over the broad market average. Luxury-tier listings commanded $470.85 per night, a $249 premium above the market average. Revenue for houses averaged $3,737 per month versus $2,641 for apartments, a gap of roughly $1,100 monthly favoring single-family properties.
On an annualized basis, the May 2026 average revenue run rate equates to approximately $39,182 per year at current performance levels. The 2025 full-year annual average was $3,825 per month, implying annualized revenue of roughly $45,900, indicating May 2026 is below the annual average as expected given seasonal timing. The revenue growth market score of 98.3 out of 100 signals strong historical upward momentum. No housing price data was available in the dataset for this area, so gross yield calculations cannot be completed here; investors should source current property values independently. One critical caveat: Chesapeake imposes a Conditional Use Permit requirement for all STRs, and properties in most residential zones cannot legally operate as STRs, making zoning verification essential before any acquisition.
Revenue Trend (5 yr)
ADR & Occupancy Trends (5 yr)
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Booking Insights
Chesapeake guests book an average of 38.4 days in advance, indicating a predominantly near-term booking market. This relatively short lead time suggests most bookings arrive within a five-to-six week window before arrival, which has practical implications for revenue management. Operators holding firm rates beyond the 40-day mark may see slower pickup, and dynamic pricing tools should be calibrated to begin offering incentives around the 30-day threshold.
Average length of stay is 4.9 nights, which places Chesapeake in a mid-stay category, not the quick weekend-getaway profile seen in some urban markets and not the seven-plus-night extended stay common in remote destinations. A nearly five-night average means fewer turnovers per booking compared to markets dominated by two-night weekend stays, reducing cleaning frequency and associated costs. Combined with the 38-day lead time, operators can reasonably anticipate demand patterns and price-adjust with a few weeks of runway.
Short-Term Rental Regulations
Chesapeake is one of the more restrictive STR markets in the Hampton Roads region. Short-term rentals are not permitted by right in most of the city’s residential zoning districts. Per the Zoning Ordinance, STRs are allowed only in two zones: the A-1 Agricultural District and the Historic and Cultural Preservation (HC) Overlay District, and only then with a Conditional Use Permit (CUP) approved through a Planning Department and City Council process.
Operators must register with the city annually for tax purposes. Transient lodging (stays of 90 consecutive days or less) is subject to an 8% transient occupancy tax plus a $1 flat fee per room per night, remitted monthly. A local business license is required, along with compliance with fire and life-safety codes (smoke and carbon monoxide detectors, fire extinguishers) and noise ordinances. Enforcement is rated strict, and the city has indicated criminal charges are possible for non-compliant operators. Specific CUP application fees, an owner-occupancy requirement, and any annual night cap were not confirmed in available sources. No major ordinance overhaul has been confirmed for 2024 through 2026; the A-1 and HC overlay framework and 8% plus $1 per night tax remain in effect. Investors must verify the specific zoning classification of any target parcel before proceeding.
Market Comparison
Chesapeake’s 56.0% occupancy in May 2026 is modestly above the US STR median of approximately 55%, and its $221.82 ADR is roughly in line with the US STR median of approximately $220. RevPAR of $124.31 reflects solid combined performance. The revenue growth market score of 98.3 out of 100 stands out as an exceptionally high signal relative to national benchmarks.
The professional management landscape is active. Village Realty leads with 351 listings and 1,976 reviews (4.38 average rating). Vacasa follows with 277 listings and 8,440 reviews (4.29 average rating). Sojourn holds 262 listings with a 4.53 average rating across 3,757 reviews, and Brindley Beach Vacation and Sales manages 234 listings with 619 reviews (4.11 rating). Christian Taylor Vacations rounds out the top five with 200 listings and a 4.57 rating across 1,552 reviews. The top five operators collectively manage roughly 1,324 listings, representing approximately 13.9% of the 9,543 total listings in the market, indicating a relatively fragmented supply where independent hosts retain majority share.
Frequently Asked Questions About Chesapeake, Virginia
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