Jacksonville Vacations from $597

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Your Jacksonville Vacation

Experience the excitement and energy of Jacksonville with a customized Jacksonville vacation package. From its welcoming locals to its lively atmosphere and beyond, you'll never have a dull moment in this city. If a sightseeing tour is on the agenda during your trip to Jacksonville, visit leading attractions like Lake Raponda, Jacksonville Pond and The Ledge. Whatever your travel plans or the size of your budget, putting together a tailored Jacksonville vacation is a breeze with Expedia.

The Latest Jacksonville vacation packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $689, price is now $597 per person
$597
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $1,397, price is now $1,027 per person
$1,027
per person
Jun 14 - Jun 20
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
9.4/10 Exceptional! (922 reviews)
The room was very clean and the beds comfortable with extra pillows and blankets. The staff friendly and the stay easy. All the amenities one needs. Breakfast coffee and small food options in lobby were a good touch. I enjoyed the taproom for dinner too.

Reviewed on May 8, 2026

Chateau Rooms

Chateau Rooms

4.5 out of 5
Price was $917, price is now $782 per person
$782
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (66 reviews)
Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again.

Reviewed on Jan 4, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $926, price is now $801 per person
$801
per person
Jun 14 - Jun 20
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
7.4/10 Good! (1,004 reviews)
Great staff and customer service. Welcoming

Reviewed on May 8, 2026

The Pico Escape: 3br/2ba Ski On/ski Off At Pico Mountain. Close To Killington. 3 Bedroom Condo

The Pico Escape: 3br/2ba Ski On/ski Off At Pico Mountain. Close To Killington. 3 Bedroom Condo

3 out of 5
Price was $3,155, price is now $2,779 per person
$2,779
per person
Jun 14 - Jun 20
found 10 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
No reviews
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Jacksonville Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$139 nightly
The price is $156 total per night from May 14 to May 15
$156 total
May 14 - May 15
Total with taxes and fees
8.8/10 Excellent! (1,008 reviews)
Super clean, great coffee spread for breakfast. I really enjoyed my stay.

Reviewed on May 9, 2026

Hotel Downstreet, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (972 reviews)
Great experience

Reviewed on May 8, 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $128 total per night from May 12 to May 13
$128 total
May 12 - May 13
Total with taxes and fees
8.6/10 Excellent! (877 reviews)
Really great place to stay in Brattleboro. Clean room, friendly and helpful staff, free coffee in the lobby and a great little bar/restaurant is attached. I'll definitely be back.

Reviewed on May 8, 2026

Latchis Hotel
See all 1,320 properties in Jacksonville
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 Jacksonville Vacation Packages

Jacksonville Essential Information

Language
English
Currency
U.S dollars
Population
220
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Mount Snow, Molly Stark State Park and The Ledge

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Frequently asked questions

How much does a Jacksonville vacation package cost?
You can pick up a vacation package to this destination from $597 on Expedia. But how much your vacation to Jacksonville costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Jacksonville?
If you're hoping to score a cheap Jacksonville vacation package, consider visiting in April, May and October. You'll generally find better prices on accommodations and flights during these months — ideal for travelers wishing to save money.
How many days is enough for Jacksonville?
The ideal length of your Jacksonville vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to visit all the top attractions and explore some hidden gems along the way.
How to find the best Jacksonville package deals?
Use Expedia's filters to find some unbeatable Jacksonville package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Jacksonville package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Jacksonville vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still get the freedom to create a tailored Jacksonville vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Jacksonville?
If you've got your Jacksonville travel dates confirmed, book as early as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Jacksonville vacation packages?
Set off on your ideal getaway to Jacksonville with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until the next payday — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals while they last.

Explore a world of travel with Expedia

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