Chesapeake Holidays

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Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
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Greenbrier East

1 out of top 10 points of interest in this area
3.5/5(2 area reviews)

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

Top hotels in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is S$80 per night from 30 Sept to 1 Oct
S$80
30 Sept - 1 Oct
includes taxes & fees
6.6/10 (552 reviews)
"The staff was very accommodating."

Reviewed on 9 Sept, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
The price is S$145 per night from 25 Sept to 26 Sept
S$145
25 Sept - 26 Sept
includes taxes & fees
7.6/10 Good! (1,686 reviews)
"The beach was beautiful and I walked out of my room to see the ocean.."

Reviewed on 8 Sept, 2025

Wyndham Virginia Beach Oceanfront
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave, Virginia Beach, VA
8.6/10 Excellent! (3,470 reviews)
"I have visited hundreds of times. That speaks for itself."

Reviewed on 10 Sept, 2025

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Schooner Inn
See all 3,398 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.

What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

S$179
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

S$31
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

S$52
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
See all activities in Chesapeake

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.