Jolliff Vacations from $339

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Your Jolliff Vacation

Say goodbye to the worries of planning and hello to a Jolliff vacation package. With your travel details organized before you leave, you can focus on discovering every inch of this city, starting with Downtown Norfolk, which is good for shopping, history and culture. Your trip to Jolliff has to include a little sightseeing. Chesapeake Square Mall is a popular place to kick things off. A few clicks is all it takes to craft the perfect Jolliff vacation on Expedia.

The Latest Jolliff vacation packages

Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Price was $446, price is now $339 per person
$339
per person
Jan 16 - Jan 20
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.6/10 Excellent! (329 reviews)
Nice location, newer rooms and great staff.

Reviewed on Dec 8, 2025

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Price was $483, price is now $381 per person
$381
per person
Jan 16 - Jan 20
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.4/10 Very Good! (1,434 reviews)
The room was very clean, and we had the top floor suite. The view was great also but what stood out to us the most was the staff. Everywhere we went, ALL the staff was so over courteous to us. I did not like to have to pay to park I think this is another way that businesses are soaking customers for more money. With what we paid for that room, the parking should have most definitely been included. $30.00 a night to park is over the top. We only stayed there because my wife's company party was there. If not for that, we would have shopped around for a place that does not charge for parking. What are you paying for anyway? They take no responsibility for your vehicle, so what do you get out of a $60.00 charge on top of your other fees they are charging?

Reviewed on Dec 7, 2025

Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Price was $711, price is now $565 per person
$565
per person
Jan 16 - Jan 20
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
9/10 Wonderful! (1,000 reviews)
Great hotel! Will stay again.

Reviewed on Dec 5, 2025

Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Central Newport News
Price was $563, price is now $456 per person
$456
per person
Feb 13 - Feb 17
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (565 reviews)
Staff was very nice and accommodating.

Reviewed on Nov 29, 2025

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
Central Newport News
Price was $511, price is now $415 per person
$415
per person
Feb 13 - Feb 17
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (1,005 reviews)
Room was nice, clean , breakfast was good

Reviewed on Dec 9, 2025

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Discover the most popular places to visit in Jolliff

Greenbrier Mall

Greenbrier Mall

4/5(260 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.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

4/5(76 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 Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene and great live music.

Chesapeake Conference Center

What to do in Jolliff

View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

$139
per adult
72% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

$40
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Wetland Zip Tour

Wetland Zip Tour

$65
per adult
98% of travellers recommend
Wetland Zip Tour
See all activities in Jolliff

Jolliff Hotel Deals

Hyatt Place Virginia Beach Town Center

Hyatt Place Virginia Beach Town Center

3 out of 5
335 Independence Blvd Virginia Beach VA
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $111 total per night from Dec 17 to Dec 18
$111 total
Dec 17 - Dec 18
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
As always the staff were wonderful. Breakfast has also greatly improved!

Reviewed on Dec 3, 2025

Hyatt Place Virginia Beach Town Center
Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Dec 16 to Dec 17
$102 total
Dec 16 - Dec 17
Total with taxes and fees
8.4/10 Very Good! (1,140 reviews)
Staff, amenities

Reviewed on Dec 2, 2025

Embassy Suites by Hilton Hampton Convention Center
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $131 total per night from Dec 14 to Dec 15
$131 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Great weekend getaway. Water was cold on my last day

Reviewed on Dec 2, 2025

Norfolk Waterside Marriott
See all 1,404 properties in Jolliff
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 Jolliff Vacation Packages

Jolliff Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Portlock Galleries at SoNo, Jillians Billiards and Oak Grove Lake Park

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Frequently asked questions

How much does a Jolliff vacation package cost?
You can pick up a vacation package to this popular destination from $339 on Expedia. However, how much your vacation to Jolliff costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Jolliff?
If you're hoping to book a cheap Jolliff vacation package, consider planning a trip in December, January and February. You're likely to find better prices on flights and accommodations during these months — ideal for a budget-friendly getaway.
How many days is enough for Jolliff?
Generally, a handful of days is enough to tick off the main attractions during your Jolliff vacation. But if you want to have some time to relax or go on day trips, consider extending your itinerary.
How to find the best Jolliff package deals?
Use Expedia's handy filters to help you find some of the best Jolliff package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Jolliff package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Jolliff vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Jolliff vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Jolliff?
If you have your Jolliff vacation dates confirmed, book as soon as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Jolliff vacation packages?
Your Jolliff trip is meant to be an escape from your busy life, not a reason for money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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