Winter Springs Vacations from $209

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $419, price is now $209 per person
$209
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
no ,black hair found in the bed

Reviewed on Feb 20, 2026

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

2.5 out of 5
International Drive District
Price was $861, price is now $268 per person
$268
per person
May 6 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
6.4/10 (1,001 reviews)
Good generally. Large cleam room

Reviewed on Feb 7, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $586, price is now $250 per person
$250
per person
May 7 - May 12
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
Todo y tal como lo muestra la foto excelente hotel

Reviewed on Feb 18, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,129, price is now $507 per person
$507
per person
Apr 12 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
Clean rooms, nice staff, good amenities!

Reviewed on Jan 25, 2026

Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
International Drive District
Save 100% on your flight
Price was $682, price is now $331 per person
$331
per person
May 7 - May 12
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (943 reviews)
We truly enjoyed our stay! The room was very clean and comfortable, and everything felt well taken care of. The staff was friendly and welcoming from start to finish. We were pleasantly surprised with a complimentary room upgrade and were able to check in earlier than the standard check-in time, which made our experience even better. We would definitely stay here again!

Reviewed on Feb 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Winter Springs
View all trips

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Discover the most popular places to visit in Winter Springs

Central Winds Park on Lake Jesup in Winter Springs, a suburb of Orlando, Florida

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 Gazebo Winter Springs, Florida

Trotwood Park

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

Trotwood Park

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

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
76% of travellers recommend
Orlando: Central Florida Zoo Skip-the-Line Ticket
Pony rides for the littlest cowboys and cowgirls!

Barn Day for Little Cowboys and Cowgirls

$5
per adult
Barn Day for Little Cowboys and Cowgirls
Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
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
Fully refundable
$124 nightly
The price is $140 total per night from Feb 25 to Feb 26
$140 total
Feb 25 - Feb 26
Total with taxes and fees
8.4/10 Very Good! (6,894 reviews)
Room has a mold smell and smoke smell

Reviewed on Feb 19, 2026

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
$133 nightly
The price is $150 total per night from Mar 19 to Mar 20
$150 total
Mar 19 - Mar 20
Total with taxes and fees
9/10 Wonderful! (6,373 reviews)
The staff support was a disappointment. My son $120 slides were stolen at the pool while he was in the pool and I was cleaning up our lunch in an area that was right near the pool. I went to security since there’s cameras there and they told me it will take a few days to investigate so luckily I ...

Reviewed on Feb 20, 2026

Universal's Cabana Bay Beach Resort
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
8101 Aircenter Ct Orlando FL
$109 nightly
The price is $123 total per night from Feb 24 to Feb 25
$123 total
Feb 24 - Feb 25
Total with taxes and fees
8/10 Very Good! (600 reviews)
We had issues with the TV in the room. We made several attempts to get it working, then took the remote to the front desk thinking that it needed batteries. The front desk clerk gave us a remote that was not compatible with the tv. Finally after several trips he came down and got the tv and remote ...

Reviewed on Feb 20, 2026

Sonesta Essential Orlando Airport
See all 4,578 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.

Find the Best Winter Springs Vacation Packages

Winter Springs Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
34,800
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Central Florida Zoo & Botanical Gardens, Sanford Museum and Wayne Dench Performing Arts Center

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winter Springs vacation package cost?
You'll find cheap prices from $209 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.