Title: Chesapeake Vacation Packages & Trips 2025/2026 from CA $1,091 | Expedia.ca

  

[Chesapeake Travel Guide](https://expedia.ca/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.ca/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.ca/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Chesapeake Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chesapeake Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

Photo by Kaylee Spinhirn

-   ## 
    
    Plan, book, travel with confidence
    

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Better together

Save up to CA $1,096 when you book a flight and hotel together\*

### 

Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

### 

Rest easy

Plan, book, and manage your trip all in one place

#### Your Chesapeake Vacation

Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. [Greenbrier Mall](https://www.expedia.ca/Greenbrier-Mall-Greenbrier-East.d6273847.Vacation-Attraction), [Oak Grove Lake Park](https://www.expedia.ca/Oak-Grove-Lake-Park-Greenbrier-West.d6301205.Vacation-Attraction) and [Chesapeake City Park](https://www.expedia.ca/Chesapeake-City-Park-Greenbrier-East.d6083011.Vacation-Attraction) are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

## Top Chesapeake Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Sunrise Inn By OYO Newport News US-60](https://images.trvl-media.com/lodging/1000000/20000/11800/11738/b2440d09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Sunrise Inn By OYO Newport News US-60

North Newport News

CA $1,091

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Norfolk (ORF)

4.8/10 (209 reviews)

Clean room, easy check in and check out. Price is reasonable. Felt safe and secure. Would stay here again if needed.

Reviewed on Sep 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-03/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11738&paandie=true&dealMarker=hde4APAjjXqaL_enEbSuKN-3CpcM_WtxKGEjUK4Ti_7NNwmrAvc7t3kAmVVXG66t)

![Spacious 4BR Home w/ Pool Family Friendly](https://images.trvl-media.com/lodging/121000000/120520000/120512800/120512753/05a7cac7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Spacious 4BR Home w/ Pool Family Friendly

Central Newport News

CA $2,648

per person

Nov 28 - Dec 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Norfolk (ORF)

No reviews

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-05/?FromAirport=YYZ&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=120512753&paandie=true&dealMarker=nmO89eKVubvPae42IwY9FxbrQqIB3e854xEEe13LW3AmBwdPyg5a60b3AVCQSyNq)

![Hampton Inn & Suites Newport News (Oyster Point)](https://images.trvl-media.com/lodging/1000000/30000/21100/21074/1e9dfcd1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hampton Inn & Suites Newport News (Oyster Point)

Central Newport News

CA $1,159

per person

Dec 6 - Dec 12

found 4 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

8.8/10 Excellent! (556 reviews)

We stayed while attending a soccer tournament in Williamsburg. The location and price was perfect, an affordable suite with kitchenette right off the highway. Dollar Tree, Subway and other shops are literally right across the parking lot and a very convenient walk. We would stay again!

Reviewed on Oct 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-12/?FromAirport=YTO&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21074&paandie=true&dealMarker=A5tXlVHbEybHXHgdewKOBI4pkk2WMf1AEr2P-InJxmuquOcS9S0nOJKTT-NEoPXi)

![Hilton Garden Inn Hampton Coliseum Central](https://images.trvl-media.com/lodging/2000000/1760000/1753900/1753824/a371073e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Garden Inn Hampton Coliseum Central

Aberdeen Gardens

CA $1,185

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Norfolk (ORF)

8/10 Very Good! (1,005 reviews)

The manager Nicole was amazing. She really helped out with some scheduling issues that I had

Reviewed on Oct 11, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-03/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1753824&paandie=true&dealMarker=hde4APAjjXqaL_enEbSuKN-3CpcM_WtxKGEjUK4Ti_7TAhbkvFEOqdQKt06ABFpt)

![Candlewood Suites Newport News/Yorktown by IHG](https://images.trvl-media.com/lodging/1000000/910000/904400/904347/013d7590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Candlewood Suites Newport News/Yorktown by IHG

Central Newport News

CA $1,192

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Norfolk (ORF)

8.4/10 Very Good! (327 reviews)

I love the kitchen , it was a very comfortable stay . Would stay here again if I ever end up in the area .

Reviewed on Aug 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-28/2026-01-03/?FromAirport=YYC&Destination=ORF&NumRoom=1&NumAdult=2&NumChild=0&hotelId=904347&paandie=true&dealMarker=hde4APAjjXqaL_enEbSuKN-3CpcM_WtxKGEjUK4Ti_7BTuZfI7ltz7akKOyzP8xM)

## Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. [Learn more about Chesapeake](https://expedia.ca/Chesapeake.dx6612)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481331-Greenbrier-Mall.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Greenbrier East

1 out of top 10 points of interest in this area

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

[Find hotel + flight trips in Greenbrier East](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20East&DestID=553248635976479827&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Greenbrier West

2 out of top 10 points of interest in this area

If you're spending some time in Greenbrier West, Bowlero Chesapeake and Rivercrest Play Area are top sights worth seeing.

[Find hotel + flight trips in Greenbrier West](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier%20West&DestID=553248635976480700&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481331-Greenbrier-Mall.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Greenbrier

1 out of top 10 points of interest in this area

If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.

[Find hotel + flight trips in Greenbrier](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Greenbrier&DestID=946137804512284672&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### South Norfolk

South Norfolk might not have many top sights, but Chesapeake Conference Center and Greenbrier Mall are two attractions nearby that you can check out.

[Find hotel + flight trips in South Norfolk](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=South%20Norfolk&DestID=553248635976388783&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481121-Chesapeake-Square-Mall.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Western Branch North

1 out of top 10 points of interest in this area

4/5(1 area review)

If you're spending some time in Western Branch North, Chesapeake Square Mall and Bowlero Western Branch are top sights worth seeing.

[Find hotel + flight trips in Western Branch North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Western%20Branch%20North&DestID=553248635976469582&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Ready to book your vacation to Chesapeake?

Choose your dates

## Chesapeake Hotel Deals

![Red Roof Inn Chesapeake Conference Center](https://images.trvl-media.com/lodging/1000000/10000/2000/1927/a9448b44_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Red Roof Inn Chesapeake Conference Center

724 Woodlake Dr, Chesapeake, VA

Fully refundableReserve now, pay when you stay

CA $100

CA $118 total

Nov 16 - Nov 17

includes taxes & fees

6.8/10 (1,005 reviews)

"Clean rooms"

Reviewed on Oct 10, 2025

[](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=1927&PinnedHotelID=1927&HadPinnedHotel=true&regionId=6612)

![STUDIOS & SUITES 4 LESS CHESAPEAKE ](https://images.trvl-media.com/lodging/1000000/50000/40500/40428/e945abb1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy, Chesapeake, VA

Fully refundableReserve now, pay when you stay

CA $78

CA $92 total

Oct 19 - Oct 20

includes taxes & fees

6.6/10 (607 reviews)

"Good"

Reviewed on Oct 16, 2025

[](https://expedia.ca/Hotel-Search?startDate=19%2F10%2F2025&endDate=20%2F10%2F2025&selected=40428&PinnedHotelID=40428&HadPinnedHotel=true&regionId=6612)

![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wingate by Wyndham Chesapeake

817 Greenbrier Circle, Chesapeake, VA

Fully refundableReserve now, pay when you stay

CA $118

CA $139 total

Nov 2 - Nov 3

includes taxes & fees

8/10 Very Good! (1,010 reviews)

"Stayed overnight because my flight was canceled, and I must say this hotel was one of the best in terms of room space and comfort. I would highly recommend this hotel!"

Reviewed on Oct 10, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=1513238&PinnedHotelID=1513238&HadPinnedHotel=true&regionId=6612)

[See all 3,400 properties in Chesapeake](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=18%2F10%2F2025&endDate=19%2F10%2F2025&regionId=6612)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### What to do in Chesapeake

![Virginia Zoo](https://mediaim.expedia.com/localexpert/1186873/7f097ff9-ed91-446b-81f3-777883b6b643.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

CA $57

per adult

**80%** of travellers recommend

[](https://expedia.ca/things-to-do/norfolks-combo-tickets-virginia-zoo-battleship-wisconsin.a1186873.activity-details)

![Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia ](https://mediaim.expedia.com/localexpert/174659/e709d57f-50ab-4b75-a124-6d7c3466f431.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Spirit of Norfolk Signature Dinner Cruise

CA $208

per adult

**72%** of travellers recommend

[](https://expedia.ca/things-to-do/spirit-of-norfolk-signature-dinner-cruise.a174659.activity-details)

![View of Spirit of Norfolk](https://mediaim.expedia.com/localexpert/434982/dcd9584b-e114-4bc2-9c6e-f55b97e7f340.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Spirit of Norfolk Signature Brunch Cruise

CA $159

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/spirit-of-norfolk-signature-brunch-cruise.a434982.activity-details)

[See all activities in Chesapeake](https://expedia.ca/things-to-do/search?rid=6612)

## Explore a world of travel with Expedia

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFPUlEQVR4Xu3aQXLbOBBGYaS80DJH0FF4NPJoPIqOkKUXrmDcP5pAE2K50pXKLKz3NpFbAD7uYHqm1P+hMg/+RSCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJFZCPMnU/Rj9q3cvtc/HnSP2y6VLfy+f2h31e2yi2jpNBCsi8DKS1jpNBCsi8DKS1jpO/K7KOn3TicJc2fLTtEfGNv+xReuezQEBAQCwQBaJAer5W3Tqyti93m/rCrfi1r9HD/nFEo/NGCwQExP4BASkgIN7XiPLtt77KW+xH/wwCUkBAPJACAlL+GtmKLvRa39s3bzb62Tf5qD+KAgFpi8ZHEBCQva0BAWmLxsfzF0KeRl5EfJWQHohGIL2nE0HqfBbIGIEoEPUayLm4fS+3+cR5NLWOk0EuRlPrOBnkYjS1jpNBLkZT6zgZ5GI0tY6TQS5GU+s4GeRiNLWOkwNy0ThRr9i1Ptr7tNrbYY58FUgFeQ5kCqSCPAcy9X0Rv6pv9bi9vUWLP3vrf/T2Oz7WV5WTCwKiQKZVBQQEBERt5Wf97WvtQo/bdcf3VdWQ0q/9rcjtvwkUEBAQEAUCUkG+RsaF3u94pVdsv9D7qPRH8Y3j6eynt+M7BQICAgKiEQiINyO6vftVPdbuB/92eaHHjb4qBAIC0uYgIG1VCATkw16LdXtf3PFzutCFnEcqPp0FAgJyGimQORCQ00i9DuJp+6OBur13c8P23/4ofXR+lHgWCAgISAUZgYDUGZl7s/dpIXJ95CfKLeXevh6j8CgeCAhI+xoEBKSCqDOytk+7neYjb7Ef/cStjL9w2+j66UIgICAgts5H3mI/goCA+NqxXa3t9o4n9tG58dY9BwICcgQCMgUCUu32Hv+XdBipM1Js1bv9JvA4PYryUQ8EpIKAnEcKpIKAVNtu/bBX7NvnN621fbnbZ9uul2ed6CO1+epj4x+8YoMUkLV9udtnEBAQEGvz1S+EVFurO17ZiUp3/N4+39s63fGqr/KnU3d74HUcC3IE4ntACgiIB3L04shTa41/u/Y7/unP2eenqyAgFghIBdFGELVWkP5lRPyL3+e/cPcL3ZEpX7MV3fE9EJAKMvI1WwHxQMZPIEe+Ziuviehv1+f/muzuezhRF7pGtso7ns6G/puABwICcuwHAQEB0WR8HMhebmNctd3veGWIkvs4ToyuP50HokBA2ioQC+QIRIH4WvumrbXkPhVPjJlbQOZA1goSAgHxQMrLIxdpu96nfbvaity4am2f+i8HY2SBgFwEAgJigYDoxNjdpltDdKHb7e3v09VPtFU60d/NvbHKAqkg4Xx1tylIDKSChPPV3aYgse+KrOMnbY+99+3uFkPMLX1jR8bIAgEBCSfuhzBGFggISDhxP4Qxsr4vMv5fakM++pZFi4uQnty46sK1QBQIyBGIWrS4gPRAQE6ILvRFi0tHdMeX/tZt1371O76f1QMBAQEBAQFJImrR4s+R0qqlvrfvhPh/c9bIV/VANAIBKSAgICCtGRn5WtseTxwtYfF2jEDi9tgSFm/HCCRujy1h8XaMQOL22BIWb8cIJG6PLWHxdoxA4vbYEhZvxwgkbo8tYfF2jP4AOXe3qb08j1fsPqr2Pn2zfx621H450B2vVbr2QyAV5CQUEBCQI5D68si/CyQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpvg/yHyp5YVS6eYxQAAAAAElFTkSuQmCC)