Jolliff Vacations from $311

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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.
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Coliseum Central
Price was $384, price is now $311 per person
$311
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (1,001 reviews)
Room was clean and nice area, also friendly staff.

Reviewed on Nov 2, 2025

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $798, price is now $565 per person
$565
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.2/10 Very Good! (1,476 reviews)
We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday

Reviewed on Oct 12, 2025

Hilton Virginia Beach Oceanfront

Hilton Virginia Beach Oceanfront

4 out of 5
Northeast Virginia Beach
Price was $837, price is now $624 per person
$624
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,040 reviews)
Loved the view. Stunning

Reviewed on Oct 27, 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 $423, price is now $326 per person
$326
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (560 reviews)
Did not eat there. TV was off and on in the evening. Toilet continually ran until I removed the top and manual closed the plunger. Other than that good stay

Reviewed on Oct 25, 2025

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
Northeast Virginia Beach
Price was $705, price is now $564 per person
$564
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,171 reviews)
Great stay. Everything was wonderful. Clean. Staff was very friendly and helpful. Will be back.

Reviewed on Nov 3, 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 great live music and acclaimed theater scene.

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

$172
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
Visit Norfolk's Perk Up Pass

Visit Norfolk's Perk Up Pass

$17
per adult
Visit Norfolk's Perk Up Pass
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
$101 nightly
The price is $118 total per night from Nov 16 to Nov 17
$118 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Hotel was nice and clean. Located in a great location. Close to everything I needed. Room was nice. There was a small area in the ceiling that needed repairs. Loved the bathroom. Breakfast was tasty. It was worth $11.

Reviewed on Nov 4, 2025

Hyatt Place Virginia Beach Town Center
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $85 total per night from Nov 11 to Nov 12
$85 total
Nov 11 - Nov 12
Total with taxes and fees
8.4/10 Very Good! (1,049 reviews)
The room was clean, modern and well designed. The front end desk clerk, Judy was wonderful and very knowledgeable about the local eateries and local food stores in the area. She recommended a bbq place for dinner, Smokey Joes, and that was just what we were looking for. The breakfast was more than ...

Reviewed on Oct 29, 2025

Comfort Suites Chesapeake - Norfolk
Hampton Inn Norfolk/Virginia Beach

Hampton Inn Norfolk/Virginia Beach

2.5 out of 5
5793 Greenwich Rd, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $104 total per night from Nov 29 to Nov 30
$104 total
Nov 29 - Nov 30
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Room was very clean.

Reviewed on Nov 4, 2025

Hampton Inn Norfolk/Virginia Beach
See all 1,358 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 $311 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.