Florida Vacations from $442
Book a Hotel + Flight or Car together to unlock savings
Your Florida Vacation
Skip the hassle of planning your next exciting adventure with a Florida vacation package. Whether you're interested in its art, food, architecture or other highlights, there's a never-ending supply of new experiences to be had. Like to explore your surroundings? Massachusetts Museum of Contemporary Art, Natural Bridge State Park and Western Gateway Heritage State Park are just three of the top-rated places to visit during your trip to Florida. Whoever you're taking a break with and whatever you plan to spend, your dream Florida vacation is only clicks away with Expedia.
The Latest Florida vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort
$451
per person
Oct 27 - Nov 1
found 2 hours ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (965 reviews)
Oak’n’Spruce is a lovely resort in a wonderful area of the Berkshires. Very nice amenities, along with pools, tennis, mini golf, ping pong and other family activities. Best of all, it’s a short drive to the charming town of Stockbridge, a short drive to Tanglewood, and another short drive to Jacob’s pillow, a wonderful indoor and outdoor dance performance venue. We stay there often, and always makes four a cultural experience and wonderful family time.
Reviewed on Aug 23, 2026
Stay near popular Florida attractions
Florida Town Hall
After visiting Florida Town Hall, make a plan to see the other sights and activities in Florida. Wander the forest and gardens while you're in the area.
Florida Free Library
After visiting Florida Free Library, make a plan to see the other sights and activities in Florida. Discover the area's mountain views and sunsets.
Florida Free Public Library
After visiting Florida Free Public Library, make a plan to see the other sights and activities in Florida. Discover the area's mountain views and sunsets.
Reed Brook Preserve
You can take time to visit Reed Brook Preserve during your travels to Florida. Discover the area's mountain views and sunsets.
Florida Hotel Deals
Blue Vista Motor Lodge
229 Mohawk Trail North Adams MA
$240 nightly
$254 total
Sep 9 - Sep 10
Total with taxes and fees
9.8/10 Exceptional! (225 reviews)
"Incredible view! Clean property! Loved our stay. Definitely recommend"
Reviewed on Aug 16, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (2,560 reviews)
"Excellent off season sky resort. Family oriented. 2 pools, indoors and out. Kids game room. Rooms are spacious, fireplace, dining table for 8, kitchen, and jacuzzi in bedroom. Couldn't ask for anything more. The night stand hand a sticky something and had to be cleaned. Otherwise, I would highly ..."
Reviewed on Aug 25, 2026
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$61 nightly
$68 total
Aug 27 - Aug 28
Total with taxes and fees
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 Florida Vacation Packages
Florida Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 690 |
Top Sights | Natural Bridge State Park, Western Gateway Heritage State Park and Clarksburg State Park |
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Frequently asked questions
How much does a Florida vacation package cost?
You can snap up a vacation package to this popular destination from $442 on Expedia. But how much your vacation to Florida costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Florida?
You can usually find reduced prices and better availability in August, October and December. Browse our cheap Florida vacation packages and you could get some great off-season deals.
How many days is enough for Florida?
The ideal duration of your Florida vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to visit all the leading attractions and discover some hidden treasures along the way.
How to find the best Florida package deals?
Finding a cheap Florida package deal is easy with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Florida package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Florida vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights separately. Better still, you can personalize your Florida getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Florida?
If you have your Florida vacation dates confirmed, book as early as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Florida vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Florida trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.