Winter Springs Vacations from $250

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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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $805, price is now $250 per person
$250
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Clean, quiet and the rooms are really nice

Reviewed on Jan 4, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,059, price is now $375 per person
$375
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
The room was spotless very comfortable, and the staff is amazing very friendly

Reviewed on Jan 7, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $673, price is now $304 per person
$304
per person
Mar 26 - Mar 30
found 23 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
We had a wonderful stay here. We came for my birthday and spent two nights, and everything exceeded our expectations. The price was great, and when we arrived, the team upgraded us to a very nice room. It looked recently remodeled, was extremely clean, and felt fresh and comfortable. Our family was very happy, and the hotel was kind enough to let us check out an hour later so we could pack up without rushing. Everyone we interacted with was friendly and helpful. Overall, an excellent experience — we would definitely stay here again.

Reviewed on Jan 4, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $522, price is now $253 per person
$253
per person
Mar 28 - Mar 31
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Stayed at this hotel because I was going to Disney the next day. The room was super clean and comfortable. Would definitely stay here again!

Reviewed on Jan 4, 2026

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Save 100% on your flight
Price was $629, price is now $315 per person
$315
per person
Mar 1 - Mar 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (1,533 reviews)
There is mold in the ceiling of my bathroom and they said the hot tub was fixed and it was not and the pool was ice cold I asked for room service to come and give me clean sheets cause I had a kid spill never showed up, also asked for new towels never showed up. I had to go down to the front desk myself to get what I needed that also included toilet paper being the maid did not do her job.

Reviewed on Jan 3, 2026

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Discover the most popular places to visit in Winter Springs

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

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

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
74% of travellers recommend
Orlando: Central Florida Zoo Skip-the-Line Ticket
Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
2-Hour Clear Kayak & Clear Paddleboar

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

$45
per adult
100% of travellers recommend
2-Hour Clear Kayak and Paddleboard(SUP) Rental in Orlando
See all activities in Winter Springs

Winter Springs Hotel Deals

Wyndham I-Drive Avanti Resort & Conference Center

Wyndham I-Drive Avanti Resort & Conference Center

3.5 out of 5
6515 International Drive Orlando FL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Jan 11 to Jan 12
$90 total
Jan 11 - Jan 12
Total with taxes and fees
7.2/10 Good! (4,065 reviews)
everything

Reviewed on Jan 6, 2026

Wyndham I-Drive Avanti Resort & Conference Center
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 Jan 13 to Jan 14
$150 total
Jan 13 - Jan 14
Total with taxes and fees
8.8/10 Excellent! (5,957 reviews)
This is the place to stay if you have children! Game room, bowling, heated pools - plenty of entertainment. The food was not the best and over priced and served like a cafeteria. But other than that, great location and great place to stay.

Reviewed on Jan 8, 2026

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
$74 nightly
The price is $84 total per night from Feb 8 to Feb 9
$84 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,559 reviews)
Very good hotel, easy on your pocket, kept very well and has lots of places around it to enjoy your stay.

Reviewed on Jan 7, 2026

Rosen Inn at Pointe Orlando
See all 4,627 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

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Frequently asked questions

How much does a Winter Springs vacation package cost?
You'll find cheap prices from $250 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.