Historical Hotels in Chesapeake, VA
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Featured Chesapeake Historic Hotels

Fairfield Inn & Suites by Marriott Chesapeake Suffolk
2122 Jolliff Rd Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Dec 28 - Dec 29
Total with taxes and fees
At Fairfield Inn & Suites by Marriott Chesapeake Suffolk, guests have access to a gym, free WiFi in public areas, and conference space. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and express check-out.
Breakfast included
Parking included

Days Inn by Wyndham Chesapeake
1439 Geo. Washington Hwy Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$53 nightly
The price is $63 total per night
$63 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at Days Inn by Wyndham Chesapeake enjoy free WiFi in public areas, free newspapers, and an ATM. A stay here includes free parking. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has a vending machine.
Breakfast included
Parking included

STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$51 nightly
The price is $61 total per night
$61 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of STUDIOS & SUITES 4 LESS CHESAPEAKE enjoy free WiFi in public areas, coffee in a common area, and a vending machine. If you decide to drive, there's free parking. Front-desk staff are standing by 24/7 to assist with any requests.
Parking included
Free WiFi

Staybridge Suites Chesapeake by IHG
709 Woodlake Drive Chesapeake VA
Free Cancellation
$118 nightly
The price is $138 total per night
$138 total
Dec 22 - Dec 23
Total with taxes and fees
Guests staying at Staybridge Suites Chesapeake by IHG enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with luggage storage and securing valuables. Additional amenities include a hot tub, conference space, and a 24-hour business center.
Pool
Hot Tub

Hampton Inn Norfolk/Chesapeake (Greenbrier Area)
701a Woodlake Dr Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $91 total per night
$91 total
Dec 28 - Dec 29
Total with taxes and fees
At Hampton Inn Norfolk/Chesapeake (Greenbrier Area), guests have access to a gym, free WiFi in public areas, and a 24-hour business center. If you drive, put free parking to good use. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and express check-in.
Pool
Breakfast included

Delta Hotels by Marriott Chesapeake Norfolk
725 Woodlake Dr Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $104 total per night
$104 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Delta Hotels by Marriott Chesapeake Norfolk have access to an indoor pool, a gym, and free WiFi in public areas. The front desk is staffed 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Pet friendly

Red Roof Inn Chesapeake Conference Center
724 Woodlake Dr Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $88 total per night
$88 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of Red Roof Inn Chesapeake Conference Center enjoy free WiFi in public areas, coffee in a common area, and a vending machine. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready.
Pet friendly
Parking included

Holiday Inn Express Chesapeake - Norfolk by IHG
721 Conference Center Drive Chesapeake VA
Free Cancellation
$79 nightly
The price is $93 total per night
$93 total
Dec 21 - Dec 22
Total with taxes and fees
At Holiday Inn Express Chesapeake - Norfolk by IHG, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a computer station.
Pool
Breakfast included

Extended Stay America Suites Chesapeake Greenbrier Circle
809 Greenbrier Cir Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $84 total per night
$84 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Extended Stay America Suites Chesapeake Greenbrier Circle enjoy a gym, free WiFi in public areas, and conference space. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. Additional amenities include coffee/tea in a common area, laundry facilities, and barbecue grills.
Breakfast included
Pet friendly

Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $93 total per night
$93 total
Dec 22 - Dec 23
Total with taxes and fees
At Wingate by Wyndham Chesapeake, guests enjoy an indoor pool, a gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

WoodSpring Suites Chesapeake - Norfolk Greenbrier
1708 Sentinel Drive Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $86 total per night
$86 total
Dec 21 - Dec 22
Total with taxes and fees
At WoodSpring Suites Chesapeake - Norfolk Greenbrier, guests have access to free WiFi in public areas, express check-out, and laundry facilities. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This smoke-free hotel also has a vending machine.
Pet friendly
Parking included

Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $79 total per night
$79 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Comfort Suites Chesapeake - Norfolk enjoy a 24-hour gym, free WiFi in public areas, and conference space. You can take advantage of free parking if you drive. The front desk is staffed 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, coffee/tea in a common area, and a computer station.
Pool
Breakfast included

Extended Stay America Suites Chesapeake Crossways Blvd
1540 Crossways Blvd Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $85 total per night
$85 total
Dec 28 - Dec 29
Total with taxes and fees
At Extended Stay America Suites Chesapeake Crossways Blvd, guests have access to free WiFi in public areas, coffee in a common area, and laundry facilities. If you decide to drive, there's free parking. Front-desk staff can help secure valuables, and provide local restaurant recommendations. This smoke-free hotel also has a vending machine.
Breakfast included
Pet friendly

Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $100 total per night
$100 total
Dec 28 - Dec 29
Total with taxes and fees
At Fairfield Inn and Suites By Marriott Chesapeake, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and express check-in.
Pool
Breakfast included

Residence Inn by Marriott Chesapeake Greenbrier
1500 Crossways Blvd Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $132 total per night
$132 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At Residence Inn by Marriott Chesapeake Greenbrier, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chesapeake hotels essential information
Accommodation | 3,388 hotels |
|---|---|
Lowest Price | $61 |
Highest Price | $138 |
Popular hotels | Fairfield Inn & Suites by Marriott Chesapeake Suffolk, Days Inn by Wyndham Chesapeake, STUDIOS & SUITES 4 LESS CHESAPEAKE , Staybridge Suites Chesapeake by IHG, Hampton Inn Norfolk/Chesapeake (Greenbrier Area), Delta Hotels by Marriott Chesapeake Norfolk, Red Roof Inn Chesapeake Conference Center, Holiday Inn Express Chesapeake - Norfolk by IHG, Extended Stay America Suites Chesapeake Greenbrier Circle, Wingate by Wyndham Chesapeake, WoodSpring Suites Chesapeake - Norfolk Greenbrier, Comfort Suites Chesapeake - Norfolk, Extended Stay America Suites Chesapeake Crossways Blvd, Fairfield Inn and Suites By Marriott Chesapeake, Residence Inn by Marriott Chesapeake Greenbrier |
Recent Historic Hotels Reviews

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
5/5 Excellent
"Great place!"
A verified traveler stayed at Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)
Posted 4 days ago
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