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Chesapeake Short-Term Rental Laws & Regulations| Chesapeake, Virginia Real Estate

Updated: Oct 31, 2023

If you’re interested in operating a short-term rental property in Chesapeake, Virginia, it’s important to be familiar with all of the current rules and regulations surrounding investment properties. Keep reading to get the scoop on where vacation rentals are allowed in Chesapeake and what regulations must be followed.

Chesapeake, VA short-term rental laws and regulations.

What is the definition of a “short-term rental” in Chesapeake?

In general, the term “short-term rental” will refer to a furnished property that is rented out for short periods, often less than 30 days. In Chesapeake, Virginia, the length of time isn’t officially defined, but there are a few important synonyms used in local laws that you should be aware of.

Many of Chesapeake’s laws governing short-term rentals refer to such properties as “bed and breakfast/tourist home establishments.” In the Transient Occupancy Tax Ordinance, the term “hotel” also applies to any short-term or vacation rental.

Take note: Hosting and rental properties marketing through apps like Airbnb, VRBO, and Homestay fall under the same laws and regulations as any other short-term rental in Chesapeake, so everything in this blog applies to those as well.


Where can I operate a short-term rental in Chesapeake, VA?

Throughout most of Chesapeake, it is illegal to run a short-term rental property.

Chesapeake Virginia’s Short-Term Rental Laws and Regulations

There are only two zoning districts in Chesapeake, Virginia where short-term rentals are permitted to operate: the A-1 Agricultural District and the Historic and Cultural Preservation Overlay District (or “HC District”). You’re unlikely to get permission from the Planning Department to start a new vacation rental outside these districts.


The Chesapeake, Virginia Agricultural District

The A-1 Agricultural District is zoned to protect and preserve the agricultural industry and rural parts of Chesapeake. Residential development is very limited in this area, so it would‌ be more difficult to access new construction to use as a rental property in this area. In this district, a property can operate as a short-term rental as its principal (or primary) use, or as an accessory use of the building.


The Chesapeake, Virginia Historical and Cultural Preservation Overlay District

Also known as the “HC District,” this area of Chesapeake was designated by City Council to preserve buildings and landmarks that have important architectural, archaeological, or cultural interest. This benefits the city’s tourist industry – which is why it could be a great area to operate a bed and breakfast rental here if you are approved.


In the HC District, short-term rentals are only able to be an accessory use of the property. In other words, the home must be the primary residence of the owner. No business should be run by an absentee owner.


There are a few others guidelines for the HC district. The owner – who lives on the property – has to be the record owner of at least 50% of the rental property. He or she could also have joint ownership with a family member.


Also, properties built after November 15, 2001 can’t be used as bed and breakfasts or vacation rentals in the HC district of Chesapeake, VA.


What permits are required for Chesapeake rental homes?

To operate a short-term rental in either the Agricultural District or HC District of Chesapeake, Virginia, you’ll need to apply and be approved for a Conditional Use Permit (CUP).


Once filed online with the Planning Department, applications are reviewed by City Council and the Planning Commission. There are several forms and documents you’ll need to include, which are listed on the City of Chesapeake website. (Make sure to apply by the 4th Monday of the month for the quickest consideration!)


The CUP process does include a public forum, so keep in mind that the public is invited to comment on your application and plans.


If your short-term rental CUP is approved, there will likely be stipulations outlined governing how you can operate the business. Those conditions will need to be followed along with all Chesapeake’s other regulations and laws listed below.


If you are not approved for a short-term rental permit in Chesapeake, you’ll have to wait at least 366 days to restart the CUP process.


If ownership of the rental property is transferred, the permit becomes void. So if the new owner wants to use it as a vacation rental as well, they will have to re-apply. Additionally, City Council does have the right to revoke CUPs for other reasons.


A Complete List of Short-Term Rental Laws in Chesapeake, VA

Here’s a list of all the short-term rental conditions and regulations that all bed and breakfasts must adhere to in Chesapeake, Virginia:

  1. Conditional Use Permit and Its Conditions: We already discussed how rental owners need a Conditional Use Permit to operate in Chesapeake. Any stipulations outlined during the process of getting that permit must be continually followed.

  2. Maximum Space Used: When you get a Conditional Use Permit from City Council, it will clarify the maximum number of bedrooms and the maximum percentage of gross floor area you can use to operate a vacation rental in your building.

  3. Length of Stay: Guests can only stay in the short-term rental for a maximum of ten days within any 30-day period.

  4. Guest Registers: The owner/operator of the vacation rental must keep a log of the names, addresses, and stay dates for each guest. All records from the past year must be available to ‌Chesapeake’s zoning administrator upon request.

  5. Off-Street Parking: Each short-term rental must provide at least one off-street parking spot per bedroom that is available for rent on the property. Parking spaces must be located behind the front building line of the residence and screened from view. (If you have a corner lot or are unsure, it’s best to check with City Council about your parking when you apply for the CUP.)

  6. Character Alterations: Chesapeake is a beautiful and unique place to stay for a reason! As such, the City prohibits any changes to the exterior appearance of the rental property or accessory structure being rented out if the updates change its residential character.

  7. Landscaping: If your property fronts ‌a street lined with small trees, you’ll need to make sure your landscaping plan adheres to article 19. City Council can help with any issues through your Conditional Use Permit process, so it’s a good idea to have a landscape plan ready when you apply.

  8. Accessory Structure Use: If your short-term rental property is in the HC District, accessory structures like garages can only be used in a manner “incidental and subordinate” to a single-family home. So it’s unlikely you’ll be approved to rent them as their own dwelling spaces.

  9. Signage: Any signs on the exterior of your property need to follow section 14-704(i) of Chesapeake’s zoning ordinance. (There’s a nifty chart on there that will help you determine the rules for your property based on type and district.)

  10. State Laws: All short-term rental homes in Chesapeake, Virginia must also adhere to any laws or regulations set for this type of business by the state of Virginia.

  11. Taxes: Don’t forget to keep up with your short-term rental taxes! Read all about them in the official ordinances here.

What are the penalties for short-term rental homes that aren’t compliant with regulations in Chesapeake?

All long-term rental homes in Chesapeake, Virginia require an inspection at least once every four years. However, there’s a good chance that your Condition Use Permit will specify a requirement for inspections as well.


If the inspector finds the property in violation of any Chesapeake laws or regulations, they may require a follow-up inspection to give you a chance to bring the rental home up to code.


If a short-term rental is operating without a permit or if it is in violation of the regulations, criminal charges may be assessed. Additionally, failing to pay the required short-term rental taxes in Chesapeake is considered a class 1 misdemeanor, so keep your books up to date.


The Bottom Line

Though Chesapeake, Virginia is a beautiful part of Hampton Roads with a vital tourist industry, opportunities for running a short-term rental or bed and breakfast here are limited. The A-1 Agricultural District and the Historical and Cultural Preservation Overlay District are the only areas where such rental operations are allowed through the Conditional Use Permit process.


If you do have the great opportunity to own a vacation rental in Chesapeake, make sure to keep all the short-term rental laws and regulations in mind.


Have questions about owning or operating a short-term rental property in Chesapeake, Virginia? Contact your local broker and real estate consultant today!



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