Chesapeake Holidays

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Our guide on where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Silhouettes of trees in Great Dismal Swamp. Virginia, United States.

Greenbrier East

1 out of top 10 points of interest in this area

If you're spending some time in Greenbrier East, Greenbrier Mall and Jillian's Billiards are top sights worth seeing.

Find hotels in Greenbrier East

Chesapeake Holiday

Our pick of the best Chesapeake Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$187 per night from 5 Apr to 6 Apr
NZ$187
5 Apr - 6 Apr
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Yes yes

Reviewed on 27 Mar 2026

Wingate by Wyndham Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is NZ$217 per night from 5 Apr to 6 Apr
NZ$217
5 Apr - 6 Apr
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
The hotel was clean, quiet, and it suited the purpose for our stay.

Reviewed on 25 Mar 2026

Comfort Suites Chesapeake - Norfolk
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is NZ$216 per night from 5 Apr to 6 Apr
NZ$216
5 Apr - 6 Apr
includes taxes & fees
8.6/10 Excellent! (411 reviews)
was ok

Reviewed on 27 Mar 2026

TRU by Hilton Chesapeake, VA
See all 3,452 properties in Chesapeake
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.

Discover the most popular places to visit in Chesapeake

A bald cypress tree in Lake Drummond in the Great Dismal Swamp Wildlife Refuge, Virginia

Lake Drummond

Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this romantic area or visit its top-notch restaurants.

Lake Drummond

Chesapeake City Hall

After visiting Chesapeake City Hall, make a plan to see the other sights and activities in Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Chesapeake City Hall

Chesapeake Central Library

Chesapeake Central Library is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its great live music.

Chesapeake Central Library

What to do in Chesapeake

View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

NZ$162
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Ziplining and Climbing at The Adventure Park at Virginia Aquarium

Ziplining and Climbing at The Adventure Park at Virginia Aquarium

NZ$109
per adult
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

NZ$71
per adult
100% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
See all activities in Chesapeake

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