Winter Springs Vacations from $219

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Your Winter Springs Vacation

Say bye-bye to the worries of planning and hello to a Winter Springs vacation package. With everything organized before you leave, you can focus on discovering the best of this city, starting with Ivanhoe Village, which is great for dining, bars and pubs and shopping. If taking in sights is on the cards during your trip to Winter Springs, swing by leading attractions like Altamonte Mall, Winter Park Village and Cranes Roost Park. Your Winter Springs vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Winter Springs vacation packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $478, price is now $219 per person
$219
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on Aug 24, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $696, price is now $303 per person
$303
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
Will refer to every one

Reviewed on Aug 24, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $625, price is now $296 per person
$296
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (3,048 reviews)
Our second visit to this property. Was very clean and convenient location for our trip. Only thing that needs improvement would be mattresses.

Reviewed on Aug 23, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,297, price is now $616 per person
$616
per person
Oct 11 - Oct 15
found 4 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
8.8/10 Excellent! (481 reviews)
Decent place. Spacious 2/2 with full kitchen and living room. A bit dated but clean. No room service and food stops at 830. Drinks are overpriced, overall a decent experience. Walking distance to the beach. Great location! Great for kids!

Reviewed on Jul 29, 2025

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $846, price is now $422 per person
$422
per person
Oct 8 - Oct 12
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Great customer service.

Reviewed on Jul 31, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Winter Springs

Tuscawilla Golf Course

Enjoy a round of golf in Winter Springs at Tuscawilla Golf Course. Stroll along the lakeside or attend a sporting event in the area.

Tuscawilla Golf Course

Central Winds Park

After visiting Central Winds Park, make a plan to see the other sights and activities in Winter Springs. Amble around the area's lakeside or attend a sporting event.

Central Winds Park

Trotwood Park

After visiting Trotwood Park, make a plan to see the other sights and activities in Winter Springs. Experience the area's acclaimed theater scene or attend a sporting event.

Trotwood Park

What to do in Winter Springs

Orlando: Central Florida Zoo Skip-the-Line Ticket

Orlando: Central Florida Zoo Skip-the-Line Ticket

$22
per adult
Orlando: Central Florida Zoo Skip-the-Line Ticket
2-Hour Clear Kayak & Clear Paddleboar

2-Hour Clear Kayak & Clear Paddleboard(SUP) Rental in Orlando

$45
per adult
100% of travellers recommend
2-Hour Clear Kayak & Clear Paddleboard(SUP) Rental in Orlando
Sailing Tour - Orlando, FL - Sailing Orlando

Private 2-Hour Day Sailing Experience

$80
per adult
Private 2-Hour Day Sailing Experience
See all activities in Winter Springs

Winter Springs Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
$98 nightly
The price is $110 total per night from Sep 4 to Sep 5
$110 total
Sep 4 - Sep 5
Total with taxes and fees
8.2/10 Very Good! (6,552 reviews)
"."

Reviewed on Aug 23, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $154 total per night from Sep 24 to Sep 25
$154 total
Sep 24 - Sep 25
Total with taxes and fees
8.8/10 Excellent! (5,147 reviews)
"One day delay Frontier cancelled a flight had to cram everything in 2.5 days already had attractions car booked caused me extra money out of pocket Will be call Expedia for some sort of compensation"

Reviewed on Aug 23, 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $68 total per night from Aug 27 to Aug 28
$68 total
Aug 27 - Aug 28
Total with taxes and fees
8.4/10 Very Good! (4,818 reviews)
"Well run, great staff. Very good prices."

Reviewed on Aug 19, 2025

Rosen Inn at Pointe Orlando
See all 4,474 properties in Winter Springs
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 Winter Springs vacation package cost?
You'll find cheap prices from $219 on Expedia for your Winter Springs escape. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Winter Springs costs.
What are the cheapest months to go to Winter Springs?
You can typically find lower prices and greater availability in July, August and December. Check out our cheap Winter Springs vacation packages and you could land some great off-season deals.
How many days is enough for Winter Springs?
Usually, a handful of days is enough to check out the top sights during your Winter Springs vacation. But if you'd like to have some time to unwind or take day tours, think about extending your itinerary.
Is it worth booking a vacation package to Winter Springs?
It's easy to see why a Winter Springs vacation is on the to-do list of many travelers. Leading attractions like Central Winds Park are just the beginning of things to keep you busy here.
How to find the best Winter Springs package deals?
Use Expedia's filter tool to find some great Winter Springs package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winter Springs package deals in the off-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 Winter Springs vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Winter Springs vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winter Springs?
Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Winter Springs trip.
How to plan a trip to Winter Springs?

  1. Pick your travel dates: The things you plan to do in Winter Springs and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter Springs.
  3. Organize your Winter Springs escape with Expedia's trip planning tool: Look for and book hotels and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Winter Springs together.
  4. Decide how many days away: Start by listing all the activities and attractions you'd like to experience in Winter Springs. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Winter Springs vacation package.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to do and see. Explore some of the best things to do in Winter Springs in Winter Springs and book your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Winter Springs vacation packages?
Your Winter Springs getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.