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
Aloft Chesapeake
1454 Crossways Boulevard
Chesapeake, Virginia
Red Roof Inn Chesapeake Conference Center
724 Woodlake Dr
Chesapeake, Virginia
Marriott Chesapeake
725 Woodlake Dr
Chesapeake, Virginia
Budget Lodge
3244 Western Branch Blvd
Chesapeake, Virginia
Wingate by Wyndham Chesapeake
817 Greenbrier Circle
Chesapeake, Virginia
Best Western Plus Portsmouth-Chesapeake Hotel
3235 Western Branch Blvd
Chesapeake, Virginia
Value Place Chesapeake Greenbri
1708 Sentinel Drive
Chesapeake, Virginia
Days Inn Chesapeake / Virginia Beach Norfolk
1433 Battlefield Blvd N
Chesapeake, Virginia
Extended Stay America - Chesapeake - Churchland Bl
3214 Churchland Blvd
Chesapeake, Virginia
Studios and Suites 4 Less
721 Conference Center Drive
Chesapeake, Virginia
Econo Lodge Chesapeake
2222 S Military Hwy
Chesapeake, Virginia
Extended Stay America Chesapeake - Greenbrier Circ
809 Greenbrier Cir
Chesapeake, Virginia
Holiday Inn Express Hotel & Suites Chesapeake
2436 Gum Rd
Chesapeake, Virginia
Baymont Inn and Suites Chesapeake
2122 Jolliff Rd
Chesapeake, Virginia
Comfort Suites Chesapeake
1550 Crossways Blvd
Chesapeake, Virginia
Super 8 Chesapeake
3216 Churchland Blvd
Chesapeake, Virginia
Hilton Garden Inn Chesapeake/Greenbrier
1565 Crossways Blvd
Chesapeake, Virginia
Americas Best Value Inn
4433 S. Military Hwy.
Chesapeake, Virginia
Comfort Inn & Suites Chesapeake
3355 S Military Hwy
Chesapeake, Virginia
Springhill Suites by Marriott Chesapeake Greenbrie
1446 Crossways Blvd
Chesapeake, Virginia
Hampton Inn Norfolk/Chesapeake (Greenbrier Area)
701a Woodlake Dr
Chesapeake, Virginia
Hyatt Place Chesapeake
709 Eden Way N
Chesapeake, Virginia
Residence Inn by Marriott Chesapeake Greenbrier
1500 Crossways Blvd
Chesapeake, Virginia
Oakwood at Chesapeake Coveside
150 Coveside Lane
Chesapeake, Virginia
Courtyard by Marriott Chesapeake
1562 Crossways Blvd
Chesapeake, Virginia
Staybridge Suites Chesapeake
709 Woodlake Drive
Chesapeake, Virginia
Days Inn Chesapeake Portsmouth
1439 Geo. Washington Hwy
Chesapeake, Virginia
Studios and Suites 4 Less Gum Road
2424 Gum Rd
Chesapeake, Virginia
Candlewood Suites Chesapeake
4809 Market Pl
Chesapeake, Virginia
Homewood Suites by Hilton Chesapeake - Greenbrier
1569 Crossways Blvd
Chesapeake, Virginia
Sleep Inn & Suites Chesapeake - Portsmouth
3280 Western Branch Blvd
Chesapeake, Virginia
Sun Suites Of Chesapeake
1520 Crossways Blvd
Chesapeake, Virginia
Savannah Suites Chesapeake
1409 Tintern Street
Chesapeake, Virginia
Hampton Inn & Suites-Chesapeake Square Mall
4449 Peek Trail
Chesapeake, Virginia
Quality Inn
100 Red Cedar Court
Chesapeake, Virginia
Extended Stay America Chesapeake - Crossways Boule
1540 Crossways Blvd
Chesapeake, Virginia
Hampton Inn & Suites Chesapeake-Battlefield Boulev
1421 Battlefield Blvd N
Chesapeake, Virginia
Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd
Chesapeake, Virginia
Hotel Tips
Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.
Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.
Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.
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 is the place to buy jewelry offered by downtown merchants with a wide variety of lovely earrings, necklaces, bracelets and of course diamond rings. You are sure to find the top artisan brands and jewelry maker that brings a special touch to each piece offered.
Chesapeake has the perfect game shop for both young and old. Your friends and family will enjoy hours of entertainment with a wide selection of board games, card games and games of skill. A perfect stop for travellers with kids and those seeking a new adventure for game night.
Why Do You Love Downtown?
Megan H.
I love being able to browse a variety of my favorite restaurants and bars, all within easy walking distance of convenient parking. Enjoying local fare and live music downtown after a grilling day at the office makes every day feel like the weekend.
Kim Ward
Unique and wonderful shopping.
Michelle Kleyne
Great vibe
Carrie Homier
6 women looking to explore the area. We will be there Feb. 18th. Whatever you can do to open our wallets easier and more economical would be much appreciated and fun! Thank you.
Jennifer Wagner
First time downtown!
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