Where to Stay in Chesapeake: Waterfront B&Bs, Luxury Hotels & Budget Options

For the discerning professional seeking accommodations that complement rather than compromise their standards, Chesapeake's waterfront luxury options deliver exceptional value. The Chesapeake Waterfront Resort stands as the region's premier establishment, with its floor-to-ceiling windows framing the Elizabeth River's gentle flow. Having secured a corner suite during my visit, I appreciated the dedicated workstation with ergonomic furnishings—a thoughtful touch for those of us who inevitably allocate time to professional matters even during ostensible leisure trips.

The Delta Hotels Chesapeake Norfolk offers another excellent option with its sophisticated maritime aesthetic. Their executive suites feature separate living areas ideal for impromptu meetings, while the pillow menu—a detail I've encountered in only the finest international establishments—ensures optimal rest. I particularly valued their executive lounge access, where I could enjoy morning coffee while reviewing documents before transitioning to vacation mode.

For those seeking more privacy, the Waterside Executive Suites provide residential-style accommodations with full kitchens and private balconies. I found their in-room coffee system particularly impressive—a significant upgrade from the standard hotel offerings that rarely satisfy discerning palates.

While luxury hotels excel in amenities, Chesapeake's historic bed-and-breakfasts offer something equally valuable: authentic regional character and personalized hospitality. The Captain's Manor, a meticulously restored 19th-century shipbuilder's home, provides an immersive experience into the area's maritime heritage. Each room features period-appropriate furnishings without sacrificing modern comforts—a balance I particularly appreciate as someone who values both historical context and practical functionality.

During my three-night stay, proprietors James and Eleanor Whitfield shared fascinating insights about local history over breakfast—information no corporate hotel concierge could provide. Their recommendation to explore the nearby Great Dismal Swamp led to an exceptional morning of birding, where my premium binoculars proved invaluable for spotting prothonotary warblers among the cypress trees.

The Mains Mansion B&B offers another excellent option in a Georgian-style home surrounded by three acres of gardens. Their Commodore Suite features a private entrance and screened porch—ideal for evening reading sessions with their collection of maritime literature. The proprietor's attention to detail extended to personalized breakfast menus accommodating my preference for South Indian coffee, an unexpected touch that demonstrated exceptional hospitality.

For travelers seeking the waterfront experience without premium pricing, Chesapeake offers several mid-range options that maintain quality standards. The Intracoastal Hotel positions guests directly along the Intracoastal Waterway with marina views and water access. Their recently renovated rooms feature locally-inspired design elements and surprisingly comfortable beds—a critical factor I assess in every accommodation.

During my exploration of Chesapeake's extensive water trails, I appreciated returning to accommodations where I could easily rinse and store my inflatable stand-up paddleboard. The hotel's dedicated storage area for recreational equipment demonstrates thoughtful consideration for active guests—a detail often overlooked by larger chains.

The Bridgewater Inn offers another excellent mid-range option with its distinctive position adjacent to the Great Bridge Lock. My room provided fascinating views of vessels transitioning between waterways—an engineering marvel that appealed to my technical background. Their complimentary water bottles proved exceptionally useful during daytime explorations, maintaining ice-cold water despite summer temperatures exceeding 90°F.

For extended stays, the Waterway Suites offers apartment-style accommodations with full kitchens and separate living areas at surprisingly reasonable rates. Their weekly rates represent approximately 30% savings compared to nightly bookings—valuable information for those planning extended visits.

While my recent Chesapeake visit focused on luxury options, my decades of business travel have taught me the value of strategic economizing. For travelers prioritizing experiences over accommodations, several budget-friendly options merit consideration.

The Chesapeake Inn & Suites, while lacking waterfront positioning, offers clean, comfortable rooms within a 10-minute drive of major attractions. Their complimentary breakfast exceeds typical budget hotel offerings, featuring hot options beyond the standard continental fare. During previous visits to the region, I've found their business center adequately equipped for impromptu work requirements.

For extended stays, the Extended Stay Chesapeake provides studio accommodations with kitchenettes at rates approximately 40% below waterfront properties. Their weekly housekeeping schedule rather than daily service contributes to cost efficiency without significantly impacting comfort. I recommend bringing your own travel pillow for these accommodations—a practice I've maintained throughout my travels regardless of property category.

Budget-conscious travelers should also consider alternative accommodations. Several well-reviewed vacation rentals in the South Norfolk Historic District offer authentic local experiences at competitive rates. During summer months, nearby Old Dominion University offers dormitory accommodations—a particularly economical option for those primarily using accommodations for sleeping rather than relaxation.

Beyond conventional hotels and B&Bs, Chesapeake offers specialized accommodations catering to specific interests—options that align particularly well with my passion for outdoor activities. The Fishing Lodge at Deep Creek provides direct water access with private docks, equipment storage, and fish cleaning stations. Their packages include guided fishing excursions targeting Chesapeake's renowned striper population—an experience I found exceptionally rewarding despite my extensive fishing background across three continents.

For cycling enthusiasts, the Trailside Inn positions guests directly adjacent to the Dismal Swamp Canal Trail. Their secure bicycle storage, maintenance station, and trail-oriented amenities demonstrate genuine understanding of cyclists' requirements. I particularly appreciated their bike repair kit available for guest use—an essential resource when I discovered my derailleur required adjustment after transport.

Those seeking wellness-focused accommodations should consider The Retreat, a boutique property offering daily yoga sessions, nutritional consultation, and spa services. Their meditation cushions and guided relaxation resources provided welcome balance to active days exploring Chesapeake's waterways. While their rates exceed standard accommodations, the integrated wellness services represent excellent value compared to à la carte pricing at conventional properties.