Jacksonville Vacations from $797

Book a Hotel + Flight or Car together to unlock savings

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.

Golden Stage Inn B&B

$797

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Rutland (RUT)

10/10 Exceptional! (45 reviews)

Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!

Reviewed on Jul 6, 2026

Mountain Green Resort

$1,610

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Rutland (RUT)

4/10 (2 reviews)

I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Suites at Killington Center

$1,473

per person

Nov 24 - Nov 28

found 1 day ago

Roundtrip non-stop flight included

Jacksonville (JAX) to Rutland (RUT)

No reviews

The Mountain Inn at Killington

$868

per person

Nov 11 - Nov 18

found 19 hours ago

Roundtrip non-stop flight included

New York (NYC) to Rutland (RUT)

9.2/10 Wonderful! (1,020 reviews)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

$921

per person

Nov 11 - Nov 18

found 19 hours ago

Roundtrip non-stop flight included

New York (NYC) to Rutland (RUT)

9.2/10 Wonderful! (67 reviews)

Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.

Reviewed on Aug 15, 2026

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Stay near popular Jacksonville attractions

Jacksonville Pond

Explore the great outdoors at Jacksonville Pond, a lovely green space in Jacksonville. Discover the area's mountain views and seek out the ski slopes.

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Stickney Hill

Commune with nature and explore the great outdoors at Stickney Hill during your travels in Jacksonville. While you're in the area, wander around the parks.

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Jacksonville Hotel Deals

Bright three-level home with water views, jetted tub, firepit, and pool table

Jacksonville VT

8.8/10 Excellent! (39 reviews)

"This was the perfect getaway on a beautiful piece of property for us to rest and relax after long days of working at my father‘s house. Everything was clean and great working condition tons of room for all of us and the property was just incredible."

Reviewed on Aug 17, 2026

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Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville VT

9.8/10 Exceptional! (46 reviews)

Great stay in cute cabin

"We had a great stay at this pond side cabin. The cabin had all we needed for our family. We really enjoyed the deck and yard in front. When it rained there were fun games in the cabin. All worked well in the kitchen , well stocked with necessary items and extras like spices, olive oil etc that are ..."

Reviewed on Aug 22, 2026

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Hotel Downstreet, an Ascend Collection Hotel

40 Main St North Adams MA

Fully refundable

$143 nightly

$160 total

Sep 22 - Sep 23

Total with taxes and fees

See all 1,315 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 $797 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.

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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.