Top Chesapeake Hotel Deals

Make the Most of Your Chesapeake Stay

A gateway to coastal Virginia's natural side

Chesapeake offers something increasingly rare among American cities: space to breathe. Formed in 1963 through the merger of Norfolk County and South Norfolk, this sprawling municipality prioritizes green corridors and waterways over dense development. The Great Dismal Swamp National Wildlife Refuge anchors the western edge with 112,000 acres of protected wetlands, while the historic Dismal Swamp Canal—surveyed by George Washington—remains the oldest continuously operating artificial waterway in the country. The city's Algonquian-derived name, meaning "Great Shellfish Bay," hints at the maritime character defining daily life here.

Dining and business convenience

The Greenbrier district serves as the commercial center, offering quality dining like Luce Secondo for handcrafted Italian pastas and The Butcher's Son for dry-aged steaks. Business travelers appreciate the concentration of hotels and meeting facilities, with Norfolk International Airport just 20 minutes away. The Great Bridge area provides different appeal, where the Revolutionary War battlefield and working lock system along the Intracoastal Waterway offer engaging breaks between meetings.

Regional access and exploration

Chesapeake's position makes it an excellent base for exploring coastal Virginia. Virginia Beach lies 20 minutes east, while Colonial Williamsburg awaits 45 minutes north. Hampton Roads Transit and Amtrak's Northeast Regional service provide options beyond driving, though a car offers the most flexibility for experiencing the region's diverse attractions.

Frequently Asked Questions about Chesapeake

Can I use my miles on Delta Stays to book hotels in Chesapeake?

Yes, you can book your hotel stay in Chesapeake using your Delta miles, or a combination of miles and cash. Simply log in to your SkyMiles® account, where you will also discover Member-only offers at select properties that could enhance your travel experience.

What is the benefit of booking my Chesapeake hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 spent on completed hotel stays and vacation rentals reserved through Delta Stays. Plus, you will receive access to Member promotions at select properties, along with the option to complete payment using miles, cash, or a combination. To ensure you earn your miles, simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies differ depending on the property you choose. We recommend reviewing the specific cancellation policy displayed under each hotel's details before finalizing your reservation. Some rates are fully refundable while others are non-refundable. Please note that if you make changes to or cancel your booking, this may affect the number of miles you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

As a Delta SkyMiles® Gold, Platinum, or Reserve American Express® Cardholder, you enjoy the advantage of earning additional miles alongside numerous valuable benefits, including an annual statement credit of up to $200 applicable toward prepaid accommodations booked through Delta Cars and Stays. Terms apply. If you would like to explore all the benefits available with your card, please visit the Delta SkyMiles® American Express Credit Cards page for complete details.

Can I earn MQDs on Delta Stays hotel bookings?

Periodically, Delta Stays provides special promotions for SkyMiles Members to earn Medallion® Qualification Dollars on accommodations reserved through their booking service. For the most current MQD earning opportunities and their associated requirements, we recommend visiting the dedicated Delta Stays MQD Offer page where you can review all available offers and their corresponding terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

Delta Stays provides hotel booking services to all customers. However, registering as a SkyMiles Member enhances your experience by allowing you to earn miles and access Member pricing and promotions. As a SkyMiles Member, you will receive 2 miles per $1 spent through Delta Cars and Stays (not including taxes and other charges). Joining the SkyMiles program is entirely free. Register today by going to the delta.com.

Can I book a vacation rental through Delta Stays?

Yes, Delta Stays extends beyond conventional hotel offerings to include a wide selection of vacation rentals for your travel accommodations. You can explore a variety of homes, condos, and specialty lodging powered by Vrbo by visiting the Vacation Rentals page.

What hotels in Chesapeake have high ratings?

You will find 47 hotels in Chesapeake to choose from when you book on Delta Stays. Delta Hotels by Marriott Chesapeake Norfolk has a guest rating of 8.6 out of 10, and features an indoor pool and a restaurant.

What's a good time of year to visit Chesapeake?

To experience Chesapeake during great weather, consider a visit in May when temperatures are pleasant and the skies are mostly sunny. For off-peak prices and fewer crowds, consider visiting during January or February when temperatures reach the 40s with lower visitor numbers and significantly reduced pricing.

Which hotels in Chesapeake are located near Greenbrier Mall?

This regional shopping center features over 100 stores and eateries, plus a Cinema Café where you can dine during movies. Families appreciate the supervised soft play area. The Founders Inn and Spa, Tapestry Collection by Hilton is a popular hotel, which is just a short drive away. Hilton Norfolk The Main is another well-reviewed hotel and it is within a short drive.

Which hotels in Chesapeake are located near Chesapeake Square Mall?

Chesapeake Square Mall combines shopping with a 12-screen Cinemark XD theater. Visit on weekday mornings for a more relaxed experience at this regional center. Popular hotels include Hilton Norfolk The Main which is a short drive away. Another top hotel is The Founders Inn and Spa, Tapestry Collection by Hilton and it is within a short drive.

Which hotels in Chesapeake are located closest to Chesapeake City Park?

This 90-acre park hosts Chesapeake's signature events like the Jubilee and Symphony Under the Stars. Families enjoy the Fun Forest Playground and peaceful walking trails. One popular hotel is The Founders Inn and Spa, Tapestry Collection by Hilton which is a short drive away. Another top hotel is Hilton Norfolk The Main and it is within a short drive.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar