Chesapeake is an independent city in Virginia, spread across a large area of suburban and semi-rural landscape south of Norfolk and west of Virginia Beach. It is not a dense, walkable city with a single centre; instead it is a collection of distinct communities connected by highways, which means where you base yourself has a real effect on how much driving you do.
For a visitor, the practical geography is defined by a handful of clusters: the Greenbrier area with its conference and business facilities, and the Woodlake area nearby, both close to the interstate corridor that links Chesapeake to Norfolk and the wider Hampton Roads region. This guide covers which of these areas to choose depending on your trip, and what kind of accommodation you will find at each budget level.
Best areas to stay in Chesapeake
1. Greenbrier
Greenbrier is the most practical base for most visitors. It is a business and commercial district with a concentration of hotels along Crossways Boulevard and Eden Way North, and it sits close to the interstate, making it straightforward to reach Norfolk, Virginia Beach and the wider Hampton Roads area by car.
It suits first-time visitors and business travellers who want reliable access to the region's road network and a choice of accommodation styles, from limited-service to extended-stay. Because the area is built around roads and commercial centres rather than pedestrian streets, you will need a vehicle to get around.
2. Woodlake
Woodlake is a smaller cluster of accommodation just off the same corridor, with hotels on Woodlake Drive. It is quieter than the main Greenbrier commercial strip but still close to the same highway connections, so it works well as a lower-key alternative base with the same access to the region.
It suits travellers who want a calmer setting while staying within easy driving distance of the business district and the routes into Norfolk. As with Greenbrier, a car is the practical way to reach shops, restaurants and attractions.
Where to stay on a budget, mid-range or splurge
- Budget: Limited-service hotels and inns in the Greenbrier and Woodlake clusters, offering basic rooms with free parking and straightforward access to the highway. Expect simpler facilities and fewer on-site services.
- Mid-range: Chain hotels and all-suite properties, some specialising in extended stays and pet-friendly accommodation, with amenities such as free breakfast, Wi-Fi, fitness facilities and indoor pools.
- Splurge: The area's full-service hotel, offering business centres, concierge services and express check-in, aimed at corporate travellers and those wanting more on-site facilities.
Best area for a first visit
Greenbrier is the best base for a first visit. It has the widest choice of accommodation in Chesapeake and the most convenient connections to the interstate, which matters in a city this spread out. Staying here puts you within easy driving distance of Norfolk, Virginia Beach and the rest of the Hampton Roads region.
Frequently asked questions
Do I need a car to stay in Chesapeake?
Yes. The city is spread out and its accommodation clusters are built around highways and commercial corridors rather than walkable streets, so a vehicle is the practical way to reach shops, restaurants and nearby cities.
Which area is best for business travellers?
Greenbrier, where the hotels are concentrated near the conference and business facilities, and where the full-service option in the city is located.
Are there extended-stay or pet-friendly options?
Yes. The Woodlake and Greenbrier clusters include all-suite properties specialising in extended stays, and at least one of these is pet-friendly.
How close is Chesapeake to Norfolk and Virginia Beach?
The main accommodation areas sit just off the interstate corridor south of Norfolk, giving quick road access to both Norfolk and Virginia Beach.
Compare live prices for the areas above using the booking tools on this page.