Downtown Chesapeake, Virginia
Discover shopping, dining, and accommodation in downtown Chesapeake.
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ShopDowntown.org Discount Card Program
The ShopDowntown.org Discount Card Program encourages local shopping by offering exclusive savings at participating downtown businesses. Shoppers can obtain a discount card by donating $20 or more to the American Cancer Society, unlocking deals of up to 15% off at local stores. The program supports small businesses, funds community health initiatives, and helps strengthen the local economy, making it a win-win for both merchants and consumers.
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Hotels
Super 8 Chesapeake
3216 Churchland Blvd
Chesapeake, Virginia
Comfort Inn & Suites Chesapeake
3355 S Military Hwy
Chesapeake, Virginia
Quality Inn
100 Red Cedar Court
Chesapeake, Virginia
Red Roof Inn Chesapeake Conference Center
724 Woodlake Dr
Chesapeake, Virginia
Residence Inn by Marriott Chesapeake Greenbrier
1500 Crossways Blvd
Chesapeake, Virginia
Baymont Inn and Suites Chesapeake
2122 Jolliff Rd
Chesapeake, Virginia
Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd
Chesapeake, Virginia
Hilton Garden Inn Chesapeake/Greenbrier
1565 Crossways Blvd
Chesapeake, Virginia
Staybridge Suites Chesapeake
709 Woodlake Drive
Chesapeake, Virginia
Budget Lodge
3244 Western Branch Blvd
Chesapeake, Virginia
Wingate by Wyndham Chesapeake
817 Greenbrier Circle
Chesapeake, Virginia
Homewood Suites by Hilton Chesapeake - Greenbrier
1569 Crossways Blvd
Chesapeake, Virginia
Holiday Inn Express Hotel & Suites Chesapeake
2436 Gum Rd
Chesapeake, Virginia
Hampton Inn & Suites Chesapeake-Battlefield Boulev
1421 Battlefield Blvd N
Chesapeake, Virginia
Extended Stay America Chesapeake - Greenbrier Circ
809 Greenbrier Cir
Chesapeake, Virginia
Hampton Inn & Suites-Chesapeake Square Mall
4449 Peek Trail
Chesapeake, Virginia
Days Inn Chesapeake / Virginia Beach Norfolk
1433 Battlefield Blvd N
Chesapeake, Virginia
Sun Suites Of Chesapeake
1520 Crossways Blvd
Chesapeake, Virginia
Comfort Suites Chesapeake
1550 Crossways Blvd
Chesapeake, Virginia
Americas Best Value Inn
4433 S. Military Hwy.
Chesapeake, Virginia
Courtyard by Marriott Chesapeake
1562 Crossways Blvd
Chesapeake, Virginia
Marriott Chesapeake
725 Woodlake Dr
Chesapeake, Virginia
Studios and Suites 4 Less
721 Conference Center Drive
Chesapeake, Virginia
Studios and Suites 4 Less Gum Road
2424 Gum Rd
Chesapeake, Virginia
Springhill Suites by Marriott Chesapeake Greenbrie
1446 Crossways Blvd
Chesapeake, Virginia
Days Inn Chesapeake Portsmouth
1439 Geo. Washington Hwy
Chesapeake, Virginia
Extended Stay America - Chesapeake - Churchland Bl
3214 Churchland Blvd
Chesapeake, Virginia
Aloft Chesapeake
1454 Crossways Boulevard
Chesapeake, Virginia
Hyatt Place Chesapeake
709 Eden Way N
Chesapeake, Virginia
Candlewood Suites Chesapeake
4809 Market Pl
Chesapeake, Virginia
Sleep Inn & Suites Chesapeake - Portsmouth
3280 Western Branch Blvd
Chesapeake, Virginia
Extended Stay America Chesapeake - Crossways Boule
1540 Crossways Blvd
Chesapeake, Virginia
Best Western Plus Portsmouth-Chesapeake Hotel
3235 Western Branch Blvd
Chesapeake, Virginia
Savannah Suites Chesapeake
1409 Tintern Street
Chesapeake, Virginia
Value Place Chesapeake Greenbri
1708 Sentinel Drive
Chesapeake, Virginia
Econo Lodge Chesapeake
2222 S Military Hwy
Chesapeake, Virginia
Hampton Inn Norfolk/Chesapeake (Greenbrier Area)
701a Woodlake Dr
Chesapeake, Virginia
Oakwood at Chesapeake Coveside
150 Coveside Lane
Chesapeake, Virginia
Hotel Tips
Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.
Not all online booking systems are fully integrated with hotel reservations systems so there is a chance that smaller hotels are hand entering your stay from a fax machine which leaves room for errors. Book directly with hotel to avoid any problems and ask for a price match if you find a better price online.
Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.
Things To Do
Chesapeake has a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.
Chesapeake keeps your pets fed, groomed, clothed and entertained with a wide assortment of ts.s available online and in-store. Does your dog need a bit of training? Check with us for great referrals to dog walkers, trainers and veterinarians who can work with your pets.
Chesapeake thanks the collection of small business owners who devote their time and energy to make shopping downtown a great experience. Inventory offered downtown is shopped by the merchant buyer to bring the best products to your neighborhood.
Why Do You Love Downtown?
Ashlee
We're visiting from Portland and we love the laid back atmosphere of this town. It is a clean and friendly town!
Robert Drennan
Planning a trip and want to visit after reading all the reviews
Liisa Shunn
We love going downtown, because we like to support our local economy. The shops and restaurants we visit -- we have gotten to know the owners, so when our money is spent downtown, we know who benefits. Also? We live only a mile from downtown, so we walk or ride our bikes. No worries about a designated driver or looking for parking. We chose to live in Medford, so of course we want our money to stay in Medford, not going off to some corporate office of a chain store.
Janet White
Never been but I love discounts! Going Today!
Devany
I love downtown because there is so much life all around. From the shoppers walking the streets to the workers stocking the stores. Everybody comes together in one place, different purposes, yet all the same. Downtown stores are always so beautiful. You can see the care workers put into making their store not only clean and beautiful, but also safe and homey.
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The American Cancer Society does not endorse any product or service.