Chesapeake Vacations from $511
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The Latest Chesapeake vacation packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
Northeast Virginia Beach
Save 100% on your flight
Price was $1,017, price is now $571 per person
$571
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,018 reviews)
Stunning views and little touches made this such a wonderful stay. Staff was very friendly and responsive. I love the thoughtful layout of the room and the spaciousness. Hands down the best stay I’ve had in VA beach.
Reviewed on Mar 29, 2026
Sea Ranch Resort
Save 100% on your flight
Price was $865, price is now $542 per person
$542
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,000 reviews)
Very spartan room which was fine as it had decent amenties. One small thing that would really help would be to fix the drapery on the window. It was hanging off the rod & made the room look terrible. Staff was friendly & efficient.
Reviewed on Mar 28, 2026
Pamlico Station Edgecamp
South Rodanthe
Save 100% on your flight
Price was $1,707, price is now $1,082 per person
$1,082
per person
May 9 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (24 reviews)
This hotel was fabulous. Staff were super friendly and made pre-check in so easy, and were very quick to respond to any questions. Everything was so clean, thoughtful, and welcoming. Amenities were amazing, relaxing and clean. Kitchen was fully equipped with everything you need and very clean.
Reviewed on Mar 18, 2026
John Yancey Oceanfront Inn
Save 100% on your flight
Price was $841, price is now $557 per person
$557
per person
Apr 30 - May 4
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
Room was cleaned every day. Staff was super nice. Breakfast had fresh fruit, muffins, and a waffle maker along with other things.
Reviewed on Mar 29, 2026
Where to stay in Chesapeake
Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Greenbrier East
1 out of top 10 points of interest in this area
4/5(440 area reviews)
While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.
Discover the most popular places to visit in Chesapeake
Greenbrier Mall
4/5(263 reviews)
You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
Chesapeake Square Mall
4/5(78 reviews)
You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.
Chesapeake Conference Center
After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.
What to do in Chesapeake
City Cruises Norfolk: Signature Dinner Cruise
$94
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
$87
per adult
88% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
$43
per adult
100% of travellers recommend
Chesapeake Hotel Deals
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $96 total per night from Apr 5 to Apr 6
$96 total
Apr 5 - Apr 6
Total with taxes and fees
8/10 Very Good! (1,010 reviews)
Breakfast was great. Front desk person was great! Price was right✅️.
Reviewed on Mar 29, 2026
Comfort Suites Chesapeake - Norfolk
1550 Crossways Blvd Chesapeake VA
Fully refundable
$98 nightly
The price is $115 total per night from Apr 5 to Apr 6
$115 total
Apr 5 - Apr 6
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Staff is extremely courteous. Great location mini stores around. Very quiet
Reviewed on Mar 29, 2026
TRU by Hilton Chesapeake, VA
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $122 total per night from Apr 5 to Apr 6
$122 total
Apr 5 - Apr 6
Total with taxes and fees
8.6/10 Excellent! (412 reviews)
was ok
Reviewed on Mar 27, 2026
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.
Find the Best Chesapeake Vacation Packages
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- Hotels near Oak Grove Lake Park
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- Portlock Galleries at SoNo
- Oak Grove Lake Park
- Cahoon Plantation Golf Course
- Chesapeake Arboretum
- Greenbrier Mall
- Jillian's Billiards
- Chesapeake Conference Center
- Chesapeake City Park
- Chesapeake Veterans' Memorial
- Children's Museum of Virginia
- Chesapeake Central Library
- Chesapeake City Hall
- Commodore Theatre
- Portsmouth Naval Shipyard Museum
- Virginia Sports Hall of Fame and Museum
- Portsmouth Vacations
- Tidewater Yacht Marina
- Frank D Lawrence Stadium
- Visit Portsmouth
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