Jolliff Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Jolliff vacation deals
Price found within the past 48 hours. Click for updated prices.
- The Ocean Key Virginia Beach Resort
Sept 1 - Sept 5The Ocean Key Virginia Beach Resort + Flight
Northeast Virginia Beach4 nights3.0 star property7.6/10 - Good (1,580 reviews)"The elevator was out of service, so we had to carry our luggage up and down five flights of stairs and walk them every time we left. The room wasn’t very clean—the floors were dirty, and it looked like the bed hadn’t been properly cleaned from the previous guests. The hot tub was closed, and despite staff saying it had just broken, it looked like it had been out of service for quite some time. The pool was also much smaller than expected. The balcony constantly smelled like marijuana from other..."Reviewed July 12, 2026Roundtrip • Toronto (YTO) - Norfolk (ORF)YYZ - ORF • 1 stop ORF - YYZ • 1 stopCA $1,165CA $947found 0 hours agoper traveller - Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Sept 1 - Sept 5Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia + Flight
Northeast Virginia Beach4 nights4.0 star property8.2/10 - Very good (1,338 reviews)"Loved balcony and beach access. Nice well stocked kitchen. Friendly staff. Overall great stay"Reviewed July 17, 2026Roundtrip • Toronto (YTO) - Norfolk (ORF)YYZ - ORF • 1 stop ORF - YYZ • 1 stopCA $1,488CA $1,146found 0 hours agoper traveller - The Barclay Towers Resort Hotel
Sept 1 - Sept 5The Barclay Towers Resort Hotel + Flight
Northeast Virginia Beach4 nights2.5 star property8.0/10 - Very good (1,002 reviews)"Facility was a bit worn but it was clean and the staff were friendly. Views of the ocean from the balcony were fabulous."Reviewed July 16, 2026Roundtrip • Toronto (YTO) - Norfolk (ORF)YYZ - ORF • 1 stop ORF - YYZ • 1 stopCA $1,392CA $1,086found 0 hours agoper traveller - Holiday Inn & Suites Virginia Beach North Beach by IHG
Sept 1 - Sept 5Holiday Inn & Suites Virginia Beach North Beach by IHG + Flight
Northeast Virginia Beach4 nights3.0 star property8.0/10 - Very good (1,425 reviews)"Not exactly what we expected from reviews. Pools and bathrooms were quite dirty and honestly not too kid friendly for those under maybe under 8 or those that can’t swim due to depth. Our room door handle was loose as well as balcony door was difficult to open. Bathroom was very tight and old carpet everywhere. It does look like they are doing renovations though, hopefully has a better future outlook. The breakfast was nice and had a great view and was located right on the beach (however no ramps..."Reviewed July 17, 2026Roundtrip • Toronto (YTO) - Norfolk (ORF)YYZ - ORF • 1 stop ORF - YYZ • 1 stopCA $1,391CA $1,122found 0 hours agoper traveller - The Colony at Virginia Beach
Sept 1 - Sept 5The Colony at Virginia Beach + Flight
Northeast Virginia Beach4 nights3.0 star property9.4/10 - Exceptional (28 reviews)"It seemed alot of people staying on the property had been long time customers, which says alot! Hopefully we can stay here again!"Reviewed July 11, 2026Roundtrip • Toronto (YTO) - Norfolk (ORF)YYZ - ORF • 1 stop ORF - YYZ • 1 stopCA $1,445CA $1,184found 0 hours agoper traveller
Jolliff Hotel Deals
Fairfield Inn & Suites by Marriott Chesapeake Suffolk
Fairfield Inn & Suites by Marriott Chesapeake Suffolk3.0 star property
Western Branch North, 1.4 km from Jolliff
8.2 out of 10, Very good, (760 reviews)
8.2/10
Very good
(760 reviews)
"Nice place to stay I will be going back if ever needed"
The price is CA $143
CA $143
CA $170 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express Hotel & Suites Chesapeake by IHG
Holiday Inn Express Hotel & Suites Chesapeake by IHG2.5 star property
Western Branch North, 2.2 km from Jolliff
7.4 out of 10, Good, (843 reviews)
7.4/10
Good
(843 reviews)
"Friendly and helpful staff very professional"
The price is CA $143
CA $143
CA $170 total
includes taxes & fees
Aug 9 - Aug 10
Candlewood Suites Chesapeake by IHG
Candlewood Suites Chesapeake by IHG2.5 star property
Western Branch North, 1.3 km from Jolliff
8.0 out of 10, Very good, (613 reviews)
8.0/10
Very good
(613 reviews)
"Love it will go again!!"
The price is CA $132
CA $132
CA $158 total
includes taxes & fees
Aug 16 - Aug 17
YourSpace Hotels Chesapeake
YourSpace Hotels Chesapeake3.0 star property
Western Branch North, 1.5 km from Jolliff
9.4 out of 10, Exceptional, (137 reviews)
9.4/10
Exceptional
(137 reviews)
"I have stayed at Your Space twice and I love it! I just wish they had a swimming pool, indoor or outdoor. The property has everything a family would need for a trip, it just needs a swimming pool. Other than that, Your Space Hotel is great!"
The price is CA $152
CA $152
CA $181 total
includes taxes & fees
Aug 16 - Aug 17
Comfort Suites Suffolk - Chesapeake
Comfort Suites Suffolk - Chesapeake2.5 star property
6.1 km from Jolliff
7.6 out of 10, Good, (1,000 reviews)
7.6/10
Good
(1,000 reviews)
"Close to several attractions and dining.
Staff was overwhelmed when I arrived"
The price is CA $148
CA $148
CA $172 total
includes taxes & fees
Aug 16 - Aug 17
American Inn Chesapeake – Portsmouth
American Inn Chesapeake – Portsmouth2.0 star property
4.4 km from Jolliff
7.0 out of 10, Good, (362 reviews)
7.0/10
Good
(362 reviews)
"Would not recommend."
The price is CA $95
CA $95
CA $115 total
includes taxes & fees
Jul 26 - Jul 27
Sleep Inn & Suites Chesapeake - Portsmouth
Sleep Inn & Suites Chesapeake - Portsmouth2.5 star property
7.3 km from Jolliff
6.8 out of 10, (631 reviews)
6.8/10
(631 reviews)
"There was something wrong with everything in our room. Everything was broken or not working right. I even had to have the refrigerator in our room replaced the very 1st night because it was warm, and I had medication with us that needed to be refrigerated. The beds were stained, uncomfortable, and disgusting. I also had to call for an extra blanket for the pull out couch that should have already been in our room, also that pull out couch was so stained, and disgusting I had to call down for...
The price is CA $117
CA $117
CA $140 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Garden Inn Chesapeake/Suffolk
Hilton Garden Inn Chesapeake/Suffolk3.0 star property
8.1 km from Jolliff
8.6 out of 10, Excellent, (1,001 reviews)
8.6/10
Excellent
(1,001 reviews)
"Highly recommended. Rooms were amazing, super clean and amazing area"
The price is CA $183
CA $183
CA $212 total
includes taxes & fees
Aug 2 - Aug 3
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.
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.
Frequently Asked Questions
How much does a Jolliff vacation package cost?
You'll find cheap prices from CA $947 on Expedia for your Jolliff getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Jolliff costs.
What are the cheapest months to go to Jolliff?
You can usually find lower prices and greater availability in January, February and November. Check out our cheap Jolliff vacation packages and you could land some great off-season discounts.
How many days is enough for Jolliff?
The ideal duration of your Jolliff vacation depends on what you'd like to do and see. Typically, a few days to a week will give you time to hit all the main attractions and explore some hidden gems along the way.
How to find the best Jolliff package deals?
Landing a cheap Jolliff package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Jolliff package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Jolliff vacation as a package?
You can enjoy significant savings on your Jolliff retreat by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Jolliff?
Secure amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Jolliff break.
How to plan a trip to Jolliff?
- Pick your dates: The things you'd like to do in Jolliff and your favourite season can help you decide when to go.
- Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your hotel will likely be the biggest expense during your trip to Jolliff.
- Decide how long to go away for: Now that you're up to speed on Jolliff, you can figure out the perfect length of your break. Create a rough plan and give yourself enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Jolliff vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.