Jolliff Vacations from $323

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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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
I liked everything. No complaints

Reviewed on Aug 11, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,760 reviews)
Great location with ocean views! We really enjoyed our stay — the view of the ocean was beautiful, and the location couldn’t be more convenient. It was just steps from local stores, eateries, and other amenities, making it easy to get everything we needed. We did have a minor cleanliness issue with ants on the first day, but management addressed it promptly and it was resolved for the rest of our stay. Overall, a great spot for enjoying both the beach and the nearby shops.

Reviewed on Aug 14, 2025

The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Sep 25 - Sep 28
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (357 reviews)
It was an excellent place to stay. The staff was phenomenal. We did not have any issues at all. Their elevator was down, but they accommodated the residence extremely well. They had a staff member stay in the elevator and help residence to get to their floors. They did a great job in a really difficult situation. The view from the hotel is amazing The boardwalk outside is incredible. You just can’t get a better place to stay!

Reviewed on Jul 22, 2025

Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,649 reviews)
Very convenient location. Staff was vwry friendly

Reviewed on Aug 14, 2025

Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

3 out of 5
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (900 reviews)
Only 3 chairs in a room designed for 4 people. Utensils for only 2 people.

Reviewed on Aug 16, 2025

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Discover the most popular places to visit in Jolliff

Greenbrier Mall

Greenbrier Mall

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

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 great live music and acclaimed theater scene.

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

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

$24
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
See all activities in Jolliff

Jolliff Hotel Deals

Casa Del Mar

Casa Del Mar

2 out of 5
1010 W Ocean View Ave, Norfolk, VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $123 total per night from Aug 18 to Aug 19
$123 total
Aug 18 - Aug 19
Total includes taxes and fees
5.2/10 (1,007 reviews)
"It takes some people time to warm up to others, however getting past the greeting, staff was great. They let me borrow a broom to keep down sand in my room. No lifeguard in pool.beach at front door. Beach happening at night. Bring tent, chairs, n tiki meet new people so fun."

Reviewed on Aug 7, 2025

Casa Del Mar
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
$127 nightly
The price is $148 total per night from Aug 24 to Aug 25
$148 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (1,004 reviews)
"The staff in the evening and morning were very nice and helpful. They did an exceptional job. I’ll come back."

Reviewed on Aug 15, 2025

Hyatt Place Virginia Beach Town Center
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $99 total per night from Aug 20 to Aug 21
$99 total
Aug 20 - Aug 21
Total includes taxes and fees
6.8/10 (1,001 reviews)
"I like the King Size Bed -- it is extremely comfortable"

Reviewed on Aug 10, 2025

Red Roof Inn Chesapeake Conference Center
See all 1,369 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.

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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 $323 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.