Title: Chesapeake Vacation Packages & Trips 2026 from CA $1,158 | 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/6608/0c611f9e-81b9-471c-8c9d-00c1df7fb2ec.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Chesapeake Vacation Packages

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

- ##  
Plan, book, travel with confidence
- ###  
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
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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.

![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/7e3313a2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### TRU by Hilton Chesapeake, VA

Greenbrier East

CA $1,158

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.6/10 Excellent! (396 reviews)

Everything was great! The room and bathroom were neat and clean. The bed was comfortable. Breakfast had many options, more than I was expecting. Check in was a breeze. It was very quiet. The location was perfect—very close to the freeway and there were restaurants very close. The only con I have is that the AC in the room sounded like there were crickets in the room when it was running. It made it somewhat difficult to fall asleep.

Reviewed on Mar 22, 2026

![Boardwalk Resort and Villas](https://images.trvl-media.com/lodging/1000000/920000/910400/910351/4f90a79f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Boardwalk Resort and Villas

Northeast Virginia Beach

CA $1,159

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.6/10 Excellent! (1,018 reviews)

Room was clean, staff very friendly

Reviewed on Mar 23, 2026

![The Ocean Key Virginia Beach Resort](https://images.trvl-media.com/lodging/1000000/530000/529400/529337/87f7858a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Ocean Key Virginia Beach Resort

Northeast Virginia Beach

CA $1,269

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

7.8/10 Good! (1,471 reviews)

I’ll admit I was a bit nervous before arriving, based on some of the negative reviews, but we had a great experience. The property is definitely older so everything isn’t perfect, but the renovations in progress are impressive. The only real cons were a slightly odd smell and the door to the balcony wouldn’t open so that was disappointing, but we still had a beautiful view from the large window. Adorable renovated kitchen, very comfy bed (smelled like bleach- nice & clean), clean floors (a big one for me) and clean bathroom. The Roma restaurant food was decent, but very convenient. The lady who worked the restaurant counter was extremely friendly. Would definitely return!

Reviewed on Mar 22, 2026

![Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/26394a34_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Northeast Virginia Beach

CA $1,235

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.4/10 Very Good! (1,215 reviews)

Helpfuly staff and great in site bar and grille

Reviewed on Mar 24, 2026

![The Atrium Resort, Virginia Beach by Vacatia](https://images.trvl-media.com/lodging/2000000/1150000/1141900/1141831/b72945f5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Atrium Resort, Virginia Beach by Vacatia

Northeast Virginia Beach

CA $1,224

per person

Apr 25 - May 2

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Norfolk (ORF)

8.2/10 Very Good! (1,479 reviews)

Staff very friendly.

Reviewed on Mar 22, 2026

## 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)

![Silhouettes of trees in Great Dismal Swamp. Virginia, United States.](https://images.trvl-media.com/place/553248635976479827/3e7f7160-d17f-4047-85a3-7e12c732b1a8.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)

![1.5 miles around. No swimming. But a playground for the kiddos, dog friendly and tons of fishing spots :) ](https://images.trvl-media.com/place/6612/a9713a83-9e8c-48e1-a2a0-408a1c201fa4.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Greenbrier

3 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)

![Newport News, Virginia, USA](https://images.trvl-media.com/place/553248635976388783/200cad18-a893-4842-a3b9-359f8cc97e65.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)

![Traveling south on the intracostal waterway. great bridge va.](https://images.trvl-media.com/place/6612/7937059d-5412-4b6d-aa49-26aec8b431f3.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Greenbrier West

 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)

![Aerial panorama of Chesapeake Bay Bridge Tunnel at sunset. CBBT is a 17.6-mile bridge tunnel that crosses the mouth of the Chesapeake Bay.](https://images.trvl-media.com/place/553248635976469582/a00ce0ef-b210-4160-a5db-1e10c2ab70e6.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Western Branch North

2 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

![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/0d94729b_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 $112

CA $132 total

Mar 29 - Mar 30

includes taxes & fees

8/10 Very Good! (1,000 reviews)

5 star

Reviewed on Mar 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=1513238&PinnedHotelID=1513238&HadPinnedHotel=true&regionId=6612)

![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/038be8fc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Fully refundable

CA $135

CA $158 total

Apr 19 - Apr 20

includes taxes & fees

8.8/10 Excellent! (1,010 reviews)

The lobby was beautifully updated BUT the elevator was not working which make carrying lounge difficult

Reviewed on Mar 23, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=6570&PinnedHotelID=6570&HadPinnedHotel=true&regionId=6612)

![TRU by Hilton Chesapeake, VA](https://images.trvl-media.com/lodging/93000000/92930000/92925200/92925103/7e3313a2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

TRU by Hilton Chesapeake, VA

1570 CROSSWAYS BLVD Chesapeake VA

Fully refundableReserve now, pay when you stay

CA $141

CA $168 total

Apr 5 - Apr 6

includes taxes & fees

8.6/10 Excellent! (408 reviews)

Everything was great! The room and bathroom were neat and clean. The bed was comfortable. Breakfast had many options, more than I was expecting. Check in was a breeze. It was very quiet. The location was perfect—very close to the freeway and there were restaurants very close. The only con I have ...

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=92925103&PinnedHotelID=92925103&HadPinnedHotel=true&regionId=6612)

[See all 3,451 properties in Chesapeake](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&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

![View of the water and the Spirit of Norfolk Dinner Cruise ship](https://mediaim.expedia.com/localexpert/174659/794d9e61-87fc-4a64-b0b9-9b590737e3a7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### City Cruises Norfolk: Signature Dinner Cruise

CA $133

per adult

**76%** of travellers recommend

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

![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 $58

per adult

**100%** of travellers recommend

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

#### City Cruises Norfolk: Signature Brunch Cruise

CA $133

per adult

**88%** of travellers recommend

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

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

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