Downtown Chesapeake, Virginia
Discover shopping, dining, and accommodation in downtown Chesapeake.
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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
Days Inn Chesapeake Portsmouth
1439 Geo. Washington Hwy
Chesapeake, Virginia
Courtyard by Marriott Chesapeake
1562 Crossways Blvd
Chesapeake, Virginia
Sun Suites Of Chesapeake
1520 Crossways Blvd
Chesapeake, Virginia
Hampton Inn & Suites Chesapeake-Battlefield Boulev
1421 Battlefield Blvd N
Chesapeake, Virginia
Springhill Suites by Marriott Chesapeake Greenbrie
1446 Crossways Blvd
Chesapeake, Virginia
Hilton Garden Inn Chesapeake/Greenbrier
1565 Crossways Blvd
Chesapeake, Virginia
Budget Lodge
3244 Western Branch Blvd
Chesapeake, Virginia
Studios and Suites 4 Less Gum Road
2424 Gum Rd
Chesapeake, Virginia
Aloft Chesapeake
1454 Crossways Boulevard
Chesapeake, Virginia
Hampton Inn & Suites-Chesapeake Square Mall
4449 Peek Trail
Chesapeake, Virginia
Residence Inn by Marriott Chesapeake Greenbrier
1500 Crossways Blvd
Chesapeake, Virginia
Studios and Suites 4 Less
721 Conference Center Drive
Chesapeake, Virginia
Extended Stay America Chesapeake - Crossways Boule
1540 Crossways Blvd
Chesapeake, Virginia
Baymont Inn and Suites Chesapeake
2122 Jolliff Rd
Chesapeake, Virginia
Hyatt Place Chesapeake
709 Eden Way N
Chesapeake, Virginia
Value Place Chesapeake Greenbri
1708 Sentinel Drive
Chesapeake, Virginia
Hampton Inn Norfolk/Chesapeake (Greenbrier Area)
701a Woodlake Dr
Chesapeake, Virginia
Wingate by Wyndham Chesapeake
817 Greenbrier Circle
Chesapeake, Virginia
Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd
Chesapeake, Virginia
Best Western Plus Portsmouth-Chesapeake Hotel
3235 Western Branch Blvd
Chesapeake, Virginia
Red Roof Inn Chesapeake Conference Center
724 Woodlake Dr
Chesapeake, Virginia
Extended Stay America - Chesapeake - Churchland Bl
3214 Churchland Blvd
Chesapeake, Virginia
Candlewood Suites Chesapeake
4809 Market Pl
Chesapeake, Virginia
Extended Stay America Chesapeake - Greenbrier Circ
809 Greenbrier Cir
Chesapeake, Virginia
Sleep Inn & Suites Chesapeake - Portsmouth
3280 Western Branch Blvd
Chesapeake, Virginia
Days Inn Chesapeake / Virginia Beach Norfolk
1433 Battlefield Blvd N
Chesapeake, Virginia
Homewood Suites by Hilton Chesapeake - Greenbrier
1569 Crossways Blvd
Chesapeake, Virginia
Staybridge Suites Chesapeake
709 Woodlake Drive
Chesapeake, Virginia
Comfort Inn & Suites Chesapeake
3355 S Military Hwy
Chesapeake, Virginia
Quality Inn
100 Red Cedar Court
Chesapeake, Virginia
Americas Best Value Inn
4433 S. Military Hwy.
Chesapeake, Virginia
Comfort Suites Chesapeake
1550 Crossways Blvd
Chesapeake, Virginia
Holiday Inn Express Hotel & Suites Chesapeake
2436 Gum Rd
Chesapeake, Virginia
Savannah Suites Chesapeake
1409 Tintern Street
Chesapeake, Virginia
Super 8 Chesapeake
3216 Churchland Blvd
Chesapeake, Virginia
Marriott Chesapeake
725 Woodlake Dr
Chesapeake, Virginia
Econo Lodge Chesapeake
2222 S Military Hwy
Chesapeake, Virginia
Oakwood at Chesapeake Coveside
150 Coveside Lane
Chesapeake, Virginia
Hotel Tips
Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.
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.
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 can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!
Chesapeake shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.
Chesapeake brings the farming community under one marketplace to offer an assortment of locally grown fruit and vegetables. Traditionally, markets are restricted to anything grown so you can expect to see natural whole foods that are sure to please those working on their plant-based diets!
Why Do You Love Downtown?
Kim Knox
All the quaint shops, I like to support small business.
Aimee Cavill
Love to wander through this beautiful town and I love the wineries!
CJ
Great vibe to this town! My mom lives in Medford so when I come to visit, I like to stop in Ashland.
Deborah
Jacksonville is utterly charming! I love browsing Terra Firma and Pickety Place, eating delicious Umi Sushi, and sitting under the amazing wisteria in the Bella Union garden. I always go to the library in that sweet little building, where Lauren the librarian knows me by name (and recommends good books). The Good Bean people are awfully nice, and even the clerks at Umpqua Bank are especially kind and friendly. Best little downtown ever!
Laura
Very charming.
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