Jolliff Vacations from $575

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Ocean Pines Resort

Ocean Pines Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.2/10 Very Good! (119 reviews)
It was bigger than I expected and the bedrooms were separated from each other which I really appreciated. Kitchen had everything we needed and the larger bedroom had its own TV which was convenient. The bed was hard and the mattress cover nearly non existent. The top sheet came off each time I moved around. Be prepared for a lack of Wi Fi and lack of cell reception. It was alittle dated but I would definitely stay here again.

Reviewed on May 4, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,781 reviews)
Very nice place on the ocean

Reviewed on Jul 2, 2025

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Norfolk (ORF)
9.4/10 Exceptional! (10 reviews)
Rooms are very nice. Like a studio apartment setup. Cozy and spacious. Beach is a very short walk away. Have plenty of restaurants, shops, and attractions nearby. Definitely going again in the future.

Reviewed on Jun 5, 2025

Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
7.6/10 Good! (35 reviews)
Property could use a bit of power washing and some paint. Update to memory foam beds, update the appliances and it will be perfect.

Reviewed on May 5, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,005 reviews)
It was ocean front with easy access to the beach. Has a nice bistro with good food. Close to stores and restaurants.

Reviewed on Jun 27, 2025

Don't see what you're looking for?
See all available trips from Columbus to Jolliff
View all trips

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

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

$139
per adult
72% of travellers recommend
Spirit of 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
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Virginia Beach: Neptune Ghosts Haunted Walking Tour

$24
per adult
Virginia Beach: Neptune Ghosts Haunted Walking Tour
See all activities in Jolliff

Jolliff Hotel Deals

Crowne Plaza Virginia Beach Town Center by IHG
Crowne Plaza Virginia Beach Town Center by IHG
3.5 out of 5
4453 Bonney Rd, Virginia Beach, VA
Fully refundable
$139 nightly
The price is $162 total per night from Jul 13 to Jul 14
$162 total
Jul 13 - Jul 14
Total includes taxes and fees
8.8/10 Excellent! (45 reviews)
"Great stay would definitely book again"

Reviewed on Jun 29, 2025

Crowne Plaza Virginia Beach Town Center by IHG
Hyatt Place Hampton Convention Center
Hyatt Place Hampton Convention Center
3 out of 5
1905 Coliseum Dr, Hampton, VA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $122 total per night from Jul 9 to Jul 10
$122 total
Jul 9 - Jul 10
Total includes taxes and fees
8.8/10 Excellent! (1,240 reviews)
"The hotel staff’s customer service was phenomenal! What a great team! I never encountered anyone who did not ask are you enjoying your stay and how can I help you!"

Reviewed on Jul 1, 2025

Hyatt Place Hampton Convention Center
Days Inn by Wyndham Virginia Beach Town Center
Days Inn by Wyndham Virginia Beach Town Center
2 out of 5
4600 Bonney Road, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $80 total per night from Jul 6 to Jul 7
$80 total
Jul 6 - Jul 7
Total includes taxes and fees
5.6/10 (1,018 reviews)
"An ok stay for the price just to go to the beach."

Reviewed on Jun 22, 2025

Days Inn by Wyndham Virginia Beach Town Center
See all 1,362 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

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Jolliff vacation package cost?
You can pick up a vacation package to this popular destination from $575 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.